When I was kid, I had this idea that to ride a bike I should learn how to balance first.

So I sat on my bike, in the driveway, trying to steady myself before I started moving. 

After watching me for a while, my mom finally shook her head, came out of the house and gave me a push. Then she ran behind, pushing the bike until I could make it go by myself.

What’s the takeaway?

There’s no stability without momentum, not with biking and often not with life.

Plus sometimes you need an outside push to get you going. 

I’ve since found paying attention to momentum to be a critical skill, particularly if you are starting something new or when you find yourself stuck.

Do you have it? No? Then, where can you find momentum? Can you use it?

It’s one of the most important lessons I’ve learned and yet it’s one I constantly had to relearn. I have a habit of pursuing passions without paying enough attention to where the wind is blowing.

For example, when I finished grad school, I was hellbent on starting a toy design company that drew on the inspiration of kids and parents in developing countries. It was creative and based on firsthand observations, but I struggled to get it going.

Finally, I managed to secure a meeting with Alan Hassenfeld, CEO of Hasbro. He listened to my pitch politely, but then told me frankly:

“This just isn’t a focus for us, let me know when you have some momentum.” 

I was devastated. But I left that meeting looking for momentum, which eventually took me to Kenya, India and Brazil working on an entirely different business. But that’s another story.

Momentum is energy, when you have it, so much more is possible. When you don’t, so much is harder or impossible.

So when you are looking to get rolling on your proverbial bike and start something new, pay careful attention to momentum.

Here are a few things to keep in mind.

Don’t take it personally

If you are in a rut, don’t beat yourself up. Being stuck is unlikely to be due to your personal value or capabilities. Not 100% any ways. You are probably just hanging out in a place with no momentum.

But you need momentum. You can’t change orbits without it.

Momentum is necessary and often sufficient

I’ve seen it again and again throughout my career, two people who are equally creative, capable and hardworking, but the one who succeeds is the one who had momentum or chose the opportunity where momentum could be found.

Product leader Michael Levinson used to advise new PMs at Facebook to think about organization first when considering what role to take: before manager, product and team. At the heart of his advice was to look for parts of the business that were stable and had momentum because it gave you the most reliable place to grow.

Building momentum by yourself takes time

In the U.S. there’s the phrase “to pull yourself up by your bootstraps” around an American ideal of being self-made.

Physics-defying nature of that phrase aside—and apparently its original use was sarcastic—in reality it’s really difficult to build momentum on your own. It takes time.

If you want to do it quickly, you almost always need external momentum or something you already have that you can turn into momentum: e.g. distribution channels, a good brand, money spent well etc.

Show up where the momentum is

In Improv Wisdom, Patricia Ryan Madson advises us to “just show up”:

"Love your parents? Pay them a visit. Need to write? Sit down at your desk. Want to have more friends? Show up at a volunteer job or a class in a subject that interests you. Need to exercise? Go to the gym or walk to the park. Believe in ecology? Take a plastic bag to the neighborhood park and pick up the trash."

Often change just comes from showing up somewhere new, where you can be surrounded by people doing what you want to do. Finding a good reason to be there is sometimes all the strategy you need.

For example, Stanley Jones once told me that his customer acquisition strategy for his mission-driven website agency was just working out of the Impact Hub in San Francisco, where he could be surrounded by people that needed his services.

It worked.

You need to paddle, but not all the time

As a surfer, you can’t catch a wave without paddling. But if you paddle too much, or too soon, you can miss the wave and exhaust yourself quickly.

So you need to take action to take advantage of momentum you find, but make the action purposeful and directed.

Practice doing what you want to do, regularly, in a place where people value it. Take breaks, ask for feedback, adjust and do it again.

And if it’s not working, try showing up somewhere new.

You don’t need to blindly follow momentum

You don’t have to go where momentum takes you, you just need to use its energy.

After all, a kite rises against the wind, not with it. You can even sail into the wind, but you can’t sail without it.

Create a Venn Diagram of 1) what you’re passionate about, 2) what you are good at, and 3) where you can take advantage of momentum, and then use it to chart a path to places you can go.

You’re looking for momentum to propel you where you want to go, or to create unanticipated opportunities you never considered.

In closing, the best way to create momentum is to borrow some that already exists.

Then do your best to stay in front of it, or to launch yourself to somewhere new.

Start pedaling, but don’t be afraid to ask for a push.

“Nothing bad can happen to a writer. Everything is material.” — Philip Roth

Throughout my career, I’ve encountered moments that really tested my resilience and determination. Whether it was dealing with exhausting initiatives, toxic leaders and systems, or just immense pressure, the challenges have been real.

During moments or periods like these, it helped me to recall Philip Roth’s quote about writers—that nothing bad truly happens to them. 

I first heard this quote from my father, a writer himself who faced an intense crucible at a young age, commanding a river boat squadron in combat during the Vietnam War. Then it was raising lots of children and supporting so many people and organizations, often while he was struggling to figure out where the money was coming from week-to-week. 

My Dad loved how Philip Roth’s quote highlighted a writer’s opportunity to transform life events, good or bad, into writing that could transcend the individual and their personal experience.

Even if a writer is struck by misfortune, that same misfortune can form the basis of a poem, a script, an essay or more. Accidents can be transformed into comedy, adversity into learning, failures into triumphs of a different sort.  

Using the lens of a writer gives you the chance to step back and view events as an observer, as input to another process or purpose. One that isn’t dependent on the failure or success of the individual events, but on what you do with them as a whole. 

And you don’t need to be a writer to gain this benefit, though I’d certainly recommend developing a regular writing practice, whether for yourself or others. 

The key is to build a mechanism or platform that can transform your challenges into “material” for something else.

Here are a few elements of a good platform:

• Serves a greater purpose: You are looking to view your individual experiences as part of a bigger or longer term objective, so there’s much less riding on each experience. For example, if you can view your efforts to develop a product as just one attempt in serving a greater mission, or just one step in your development as a product manager, then you will be much more resilient. 

• Is related but diversified: You want your platform to connect easily to your work or your efforts, but at the same time you’re looking for the ability to transform failures into learning or success. For example, blogging about your experiences writing a novel is not very diverse, as it could suffer from similar risks. On the other hand, convening a meetup of aspiring novelists is less exposed to the same risks and provides more diverse benefits.

• Connects you to others: One of the biggest traps when you are in midst of intense efforts or experiences is get stuck in your own head and to not reach out to others. A great “material” platform is one that naturally connects you to other people and their perspectives. 

• Shows your work in a good light: An effective “material” platform is one that disposes both you and other people to view your failures and successes in a positive light. For example, if you are sharing a chronicle of your experiences, would it be better to frame it as an expert’s journey or a learner’s journey?  

For further brainstorming, it can also be helpful to try on a few different lenses for what your platform can focus on:

• Teaching others: Your own failures and what you learned can create meaningful value for people facing similar challenges. Even when you’re in the midst of a challenging situation, you can reflect on how you would frame it and what you learned to gain some emotional distance from the situation.

• Supporting others: Therapists and social workers can leverage their personal challenges to deepen their empathy and understanding of the people they serve. You too, can reflect on the groups you would be better able to connect to and help given your experiences.

• Engaging or entertaining others: Speakers, comedians and all types of leaders use their personal stories to infuse authenticity into their work. Consider how your experience can help you demonstrate such authenticity and what audiences it might engage.  

Become like water

Ultimately, you are looking to build on Bruce Lee’s imagery of water:

"When you pour water in a cup, it becomes the cup. When you pour water in a bottle, it becomes the bottle. When you pour water in a teapot, it becomes the teapot. Water can drip and it can crash."

Create a form to hold the “water” of your experiences and to generate the “material” for something even greater. 

Don’t just let your experiences direct your life.

Create a container to transform them into something greater.

It was 2006, I was on a boat in Hussain Sagar, the heart-shaped lake in the middle of Hyderabad, India. My colleague Erik and I had just finished a first, intense month researching and developing novel business concepts for Dupont to address protein deficiencies in the urban slums of Hyderabad and nearby villages.

We decided that we and our team—made up of local professionals—could use a break, and an evening cruise by the world famous Buddha Statue of Hyderabad seemed like a great opportunity for some calm reflection.

However, once we approached the giant statue, loud music started blaring from speakers onboard and our colleagues and everyone else on the boat rushed over to watch a group of performers dance and lip sync to the music. Minutes later the dancers parted and a ventriloquist with a Donald Duck mannequin came out on stage.

It all seemed so bizarre. Here we were, floating aside this incredible landmark, but Erik and I were the only ones looking at it. No one else paid the Buddha any attention.

Then struck by a sudden insight I turned to Erik and said:

“You realize that we are the weird ones here, right?”

As I’ve written about before, my career has been decidedly non-linear, which has led to a fair number of “fish out of water” moments like the above.

Whether that was from working in a new country or culture, switching domains or companies, or just trying to work with a new group of people.

You may have experienced similar moments, too, perhaps acute like the Buddha example above or more subtle. Times when you just can’t seem to make sense of the behaviors around you or you feel a nagging sensation that people just don’t view the world like you do.

When you experience that feeling, it’s helpful to question if you’re the weird one.

Because while the behavior you are observing may seem strange, invariably there is a system of motivations and incentives that underlie it, an established structure in which the behavior makes sense… and where you don’t.

I guarantee you there is, even if you can’t see it. At least not with what you know now.

Whether you want to change that behavior or integrate with it, I have found that you are much better off accepting that such a structure exists. And accepting that you are most likely the outlier.

You are the weird one.

Once you do accept it, there are a few strategies you can then take to help you both manage and take advantage of being weird.

• Find translators - Look for people that both understand your reality but also appreciate the new one you’re facing. They can empathize with your experiences and provide emotional support. But even better they can help you understand the weirdness you observe, and whether and why it’s actually you that is weird. Be careful to look for people that can see the positives in both realities, not just grumble about the negatives.
  

• Practice reflective journaling - Keep a journal where you reflect on your experiences, observations and interactions in new or unfamiliar situations. Write down any insights, challenges or lessons learned, and identify areas for growth and improvement. If you have found translators, share parts of your journal with them to get their feedback and insights.
  

• Build common ground - Look for commonalities and shared values that can serve as a bridge between your perspective and those of others. Even better, find something quick that you can build together, based around your mutual interests or goals. The act of building will quickly bring to light the differences in your world views, but also begin establishing context and trust for future efforts.
  

• Discover points of leverage - If you are looking to change yourself or the behavior of the people around you, look for intersections between what you can offer and what people value. These intersections are incredibly fertile ground for innovation and new opportunities, but you can only identify them if you first appreciate the differences that exist.

In the end, with any new situation or effort there is a real challenge in being different. It can be tiring, confusing and often demotivating.

But whether you are looking to just cope, or to assimilate, or even to make the world change, it all starts with accepting your own weirdness in the eyes of others.

You’ll be better off for it.

If you find these posts insightful, consider subscribing to my Probable Wisdom newsletter or following me on LinkedIn. Plus share your own wisdoms in the comments, if I’ve learned anything, it’s that there is still so much to learn.

Small Wisdom 1: Gratitude has transformative power

Whenever I’ve felt stuck, expressing gratitude has been one of the most sure fire methods to help me get out of whatever rut I am in.

This has been true for both me as an individual, but also as a practice for the teams and organizations I have led.

That’s because gratitude has a transformative power to shift your perspective. 

Instead of allowing our brains to be hijacked by thoughts of what we lack or what’s going wrong, expressing gratitude diverts your thinking out of its negative spiral and back on to a positive track as you acknowledge and celebrate the blessings that have graced you, big and small.

As an individual, embracing gratitude means recognizing that those blessings have come from outside of yourself. It reminds you that you wouldn’t be where you are, if it weren’t for someone or something else. It preps you to accept the help that you need.

As an organization, gratitude means celebrating the contributions and victories of your team, but also recognizing the factors and conditions that helped you succeed.

In short, gratitude makes you look up and look around, which is a requirement if you want to go somewhere new with any real probability of success. 

I mean, with your eyes down you could stumble and grumble onto something new, but is it likely?

Want some help expressing gratitude? Here are a few methods that have worked for me.

Gratitude rampage

I was introduced to this method in coaching training, which you can use anytime you want to bring your mind into a more positive state: for example, before an interview, when tackling something creative, or before a potentially difficult conversation.

Set a timer for 5, 10 or 15 minutes, open a blank document, and start naming the things your are grateful for and why.

A variation of this that I’ve used during team meetings, is to write down 3 to 5 things you are grateful for. Work with your team to name the source or cause of those good things before moving on to the rest of your meeting.

Gratitude letters

Write an email or letter to someone you never properly thanked. We all have people who impacted our lives positively, many of whom you may have never had the chance to thank… or didn’t realize their impact until much later.

Delivering a message of gratitude also gives you the chance to reconnect, which can be especially valuable if it’s someone you have fallen out of touch with. And research has shown that reactivating these so-called “dormant ties”*—people you once had a strong connection to—can be particularly beneficial when facing difficult obstacles.  

*Thank you Michael Soto for introducing me to the concept.

Reflecting on the life of a loved one

When you experience the passing of a loved one, as I have recently, it can be extremely cathartic to look back on their life and reflect on how much richer your life is for having had them in it. 

Of course, you don’t need to wait for someone to pass to do this. Identify someone who has inspired you or impacted your life and reflect on how they did it. You could even write them a gratitude letter with your reflections.

You can also do this for organizations or even products that you feel grateful for. Think about how they were able to impact your life and why to get inspiration for how you might do the same for others.

“Gratitude makes sense of our past, brings peace for today, and creates a vision for tomorrow.” - Melody Beattie

I have found gratitude to be a simple yet powerful practice that has the potential to transform your life and your current situation.

So let’s all take a moment to reflect on the people and things we're grateful for.

Not only do we get to observe and honor what is good in our world, but we greatly improve our chances to make that world even better.

If your company has invested heavily in developing internal tools, those efforts could be fertile grounds for a new commercial offering. 

Amazon AWS started as an internal shared IT platform. Meta’s Workplace began as an employees-only version of Facebook. Slack was a modern IRC platform for developers of the video game Glitch. All three went on to be highly successful products when transitioned from internal-only to public product. 

I have been lucky to work on several efforts to transform core internal tools to commercial products—including Workplace at Facebook and P2 at Automattic—and I became a firm believer that innovation used to solve your own problems can offer compelling solutions to other companies’ problems, too. 

At the same time, I have also witnessed five product building anti-patterns for crossing the internal-to-external “chasm”. Managing around these traps is critical to bringing an internal tool to market, or if you can’t, determining quickly that your efforts are better spent elsewhere.

Anti-pattern 1: Assume your customers look like you

The core hypothesis in transforming internal tools to public products is that other companies face the same problems that your tool solves. However, this can lead to a false assumption: that your ideal customer should look like your company, or to put a finer point on it, to misunderstand what you share in common.

When Facebook at Work was first introduced, we assumed tech startups would be our ideal customers: not only was their mode of working most similar to Facebook’s, but we felt we understood them best as we often partnered closely on other products. 

But the real breakthrough opportunity came from customers like Walmart and Starbucks who wanted to use the product (re-branded as Workplace) to connect their “frontline” employees. We assumed it would be used by desk-based tech folk with great Wi-Fi, but Workplace found market fit with companies where mobile workers used the product in a very different way. 

You still need to validate your ideal customer and it may not be you.

Anti-pattern 2: Rely on [your] culture

At Automattic we had the saying “P2 or it didn’t happen” which was the expectation that a representation of your work—whether code, designs, meetings, research etc.—would be posted to our WordPress-based collaboration platform so that everyone in the company could see it. This practice was a powerful cultural norm that has enabled Automattic to thrive as a fully-distributed, global company for more than 15 years.

Yet when we talked to potential customers of P2, many of them struggled with the idea of implementing a similar practice, even when the pandemic drove them to transform to a remote workplace like Automattic.  

In short, if your tool is an extension of your internal company culture, don’t rely on the practices of that culture to exist or be adopted by your customers. 

Anti-pattern 3: Not prioritizing between internal and external users

It’s common for the same team that’s working on transforming a tool into a product to also end up responsible for its internal use.

Given the internal needs for the tool are clear and support the existing business, in the early days they can outweigh the yet-to-be-known value of solving problems for external customers. It’s also easy to think that improving something for an internal user will translate to external customers as well. It often won’t.

The end result is a form of the Innovator’s Dilemma, where a disruptive innovation is smothered by a company’s traditional business, but in this case it’s the company’s internal needs that can smother a tool’s external market potential. 

Successful companies manage this trade-off intentionally, creating a decision-making framework for how improvements will be prioritized. Even better, they also build their tools as platforms to support both internal and external clients, much as Amazon did with their API Mandate. This practice made possible AWS, Fulfillment by Amazon, Alexa and other successful Amazon services. 

Anti-pattern 4: Focus on advanced capabilities vs. beginner problems

By nature, your company is already highly experienced using your internal tool. You may have developed advanced features that leverage the tool’s capabilities. But you have to be careful not to let your intimate familiarity with your internal tool blind you to the challenges that newcomers face. 

For example, a typical mistake is to prioritize development of an onboarding experience that demonstrates the advanced features of your product, “tool-tipping through the learning curve”. Instead you should be focused on discovering the core problems that beginner users want addressed, and evolve your product to capably satisfy those. 

No ones going to stick around for your advanced capabilities if the beginner problems are not compelling and clearly addressed.  

Anti-pattern 5: Overlook go-to-market alignment challenges

If your main business is a consumer offering, or if your go-to-market motion is primarily product-led and small-team focused, then you’re probably under equipped to tackle an enterprise or mid-market GTM motion. 

Likewise, if you’re primarily enterprise sales-driven, but your internal product aligns better with teams than whole organizations, then you may need to adopt a product-led growth strategy, which you may not have the staff and systems to support. 

Even if you’re used to selling to enterprise customers, your new product may require sign off from a whole different cohort of stakeholders: in my experience, marketing platforms, CRMs and internal collaboration systems all have different owners. 

This all could require developing systems or capabilities you didn’t have previously.  For example, with Workplace, Facebook quickly realized the need to build entirely new customer success teams that were experienced with enterprise software, focused on the support and training of internal champions for Workplace to gain a foothold in a prospective company.  We also needed to update the product to meet customers’ security and admin requirements. 

Ultimately, building new go-to-market capabilities can be time consuming and expensive. So you should first validate the level of alignment between your product, people and processes with what’s required of the new opportunity.

Not to mention validating whether or not all that effort would be worth it. 

Value is not what you already built

With internal products, you start with something that is already built, which already creates value for you.

If you want to launch an external product though, you need to focus extra hard on how it will be used by external customers. You need to internalize the problems they will use your product for, and how they will learn about it and adopt it. 

Set aside the value your internal tool creates from your company’s use, and instead envision it as a set of capabilities to solve problems for potential customers.

Use that as your north star.

You may find you can unlock incredible value for them and for you.

The value is in what gets used, not in what gets built. ​– Kris Gale

I hate bad modeling. I consider it an abomination. 

By bad modeling, I mean models that depict what people want to be true, vs. what is actually true. Or models that focus on potential and then get all hand wavy about probability. 

“There are a billion people buying widgets every year, with just $1 from each we will have a billion dollar business!”

Yeah, impressive potential, but how probable is it?

I would assume not very, until proven otherwise. 

Most detailed models will be expressed in a spreadsheet, such as estimates for a new product, partnership, campaign etc. It could have multiple rows and columns representing calculations across multiple months or years. It might even be color coded for readability. 

The story generally starts with real data, i.e. a billion people buying widgets, but the problem is that somewhere along the line it often turns into science fiction. 

How does science differ from science fiction?

There’s no fiction in science.

Most models contain key variables that the whole thing hinges on. Those variables become fiction when you input assumptions and accept them as true without validating the probability for them to actually be true.

You are better off accepting that your input assumptions are unlikely to be true, and then spend time to prove what they actually are.

To illustrate this, consider one of my favorite jokes.

I mean, it’s funny because “assuming a can opener” is obviously ridiculous. But what if it were less obvious? 

What if the three spotted a crate on top of a mountain and they needed to decide if it would be better to try to open the can of beans now or to send someone up the mountain to discover if the crate contains anything that could help?

The crate represents an unknown opportunity, but even then I would argue that they are better off assuming a low probability that the crate has what they need vs. relying on it, especially if the mountain is high and the path is risky.  

In short, unvalidated assumptions in models are dangerous because they can skew the whole model and lead you to invest too much in the wrong thing.

But also because they distract you from the reality you actually have to work with.  

Over the years I have seen so many models with unvalidated assumptions stacked on top of each other, like an endgame of Jenga, but instead of wooden blocks you have a tower of stacked can openers… which may or may not be there.

An abomination. 

So how should we use models?

I have found models to be most powerful when you use them as part of a discovery process. Treat them as an exercise to identify killer assumptions, i.e. ones that will make it all work if they are true, but that would upend your efforts if they are not.  

Then focus on validating and determining your ability to manipulate the underlying probabilities of those assumptions.   

As an example, below is a very simplified model for a proposed distribution partnership, where your product is offered as a free trial to new customers of the partner. 

• Number of new customers x Offer opt-in rate x Activation rate x Renewal rate (post-trial)

If this is all brand new (unproven), you should assume a heavy discount rate—a low probability—for each of those variables until you can 1) validate what they actually are, and/or 2) convincingly manipulate them to improve.

For example, you could:

• Get data from your partner on the performance of similar offers, to establish a ballpark

• Conduct quick test campaigns and user research with the partners customers

• Ask the partner to compensate you for the free trial, to gauge how certain they are of success 

• Explore cost-effective ways to remove friction from the experience, e.g. bundling the free trial automatically, making the offer an opt-out etc. 

Using what you learn, either update the model, or focus on efficient investments to improve your probability of success.

Or walk away, that’s an option, too.

What you shouldn’t do is start a heavy engineering investment to support the partnership, use the model to determine your quarterly goals, etc. 

To borrow an analogy from my old colleague Erik Simanis, your goal is to determine if your efforts can “take a punch in the mouth” and keep standing. And to identify if there are key elements you need to strengthen or obstacles you need to remove.

The job of a model is to help you discover the truth, not to stand in for the truth.

“All truths are easy to understand once they are discovered; the point is to discover them.” - Galileo

Addendum: What about forecasting?

I am of the camp that forecasting should only use data that is known to be true or likely to be true. 

For new products or initiatives, that’s often not the case, and while I’ve seen teams use some variant of high, medium, and low demand estimation to model this, most of the time they are not nearly conservative enough. 

For initiatives with unvalidated assumptions, your worst case scenario is not achieving 30% of your forecast, it’s achieving 0%. And in my experience 0% is closer to the truth than you initially think.

So don’t include assumptions that are unproven and material in your forecast models, especially if you intend to measure performance based on them. 

"Assumptions are made, and most assumptions are wrong." - Albert Einstein

My career hasn’t always followed a straight line. 

I’ve worked as a software engineer, product manager and partnerships lead in Silicon Valley, but I’ve also spent years as a social entrepreneur and sustainable development consultant in Kenya, India, Brazil and the U.S.

I’ve developed AI assistants for NASA and launched new developer platforms for Facebook and Automattic, but also worked on latrine cleaning services and soy protein sales in the urban slums of Nairobi and Hyderabad.

I’ve experienced more than one restart moment in my career, either because I decided to jump into something new or life just came along and called “time out”.

And these days, I am increasingly running into people with similar experiences, navigating “non-linear” careers like me, or starting over to tackle something new.

Also like me, sometimes that’s been voluntary, sometimes a response to circumstances.

For everyone I’ve met, I have heard stories about the challenges in navigating a non-linear career, but also about a lot of joy as well.

For example, if I had just stayed an engineer at Apple all those years, my career story would be a lot simpler to tell to recruiters. I’d probably be richer, too.

But my life sure would have been a lot less interesting, and my potential for impact, a lot smaller. I would have missed so many incredible experiences and people.

I have zero regrets.

Still, today’s hiring environment represents additional challenges for people with non-linear careers. I’ve found this to be true for me personally, but also for others I have worked with as an advisor and coach.

For every new role, companies are awash in applications and many are using some form of pattern matching to manage the volume. If your career didn’t follow a straight line, you may find fitting the prescribed patterns to be a difficult task.

Even just to get a foot in the door, you need to be extra considerate about the opportunities you pursue and how you go after them.

If you want to maximize your probability of success, here are a few strategies I have found to be helpful.

• Look for opportunities where being non-linear gives you super powers

• Customize a story of your career as a narrative to match the opportunity

• Cultivate a network of people who value the intersections in your career

Places where non-linear is a super power

You want to find opportunities where the diversity of your career is considered a strength, and not a liability. Below are a few broad areas where I have personally found that to be true.

Do you know of others? I’d love to hear about them in the comments.

1) Bridging multiple domains 

Experience working in different domains can enable you to be a very effective translator, whether that’s between sectors like healthcare and AI, or between different roles, like engineering and sales.

Even if you haven’t worked in one of those domains, having already been an “expert turned newbie” you are better positioned to translate for a new domain. 

In other words, you have experienced not know everything, and you know any one domain is unlikely to have all the answers. That’s a strength. 

“Modern work demands knowledge transfer: the ability to apply knowledge to new situations and different domains. Our most fundamental thought processes have changed to accommodate increasing complexity and the need to derive new patterns rather than rely only on familiar ones. - David Epstein: Range

2) Turnarounds

Leading turnarounds is another area where people who have more breadth of experience can shine, particularly when you’re talking about turnarounds that became necessary due to external factors*, such as changing market conditions. 

Your greater breadth means you have more exposure to other approaches, and the ability to understand and learn from other domains can greatly increase your options and your probability of success. 

You also probably have seen a wider range of failures and success, are unlikely just to insist to keep doing what already failed, like the proverbial hammer in search of a nail.

[* Stakeholders can often conflate internal and external factors. If you’re considering tackling a turnaround, check out my last post on the subject]

3) Entrepreneurship and creators

Starting something new can greatly benefit from a broader experience base. Research has demonstrated that exposure to diverse experiences can enhance individuals' creativity and innovation capabilities.

Entrepreneurs who have worked across multiple domains or industries may bring fresh perspectives and unconventional solutions to business challenges, which can be compelling to investors looking for novel and disruptive ideas.

This is especially true if you’re working to intersect domains where you have experience, say applying expertise or familiar technology to another area you are intimately aware of.

When you step into an intersection of fields, disciplines, or cultures, you can combine existing concepts into a large number of extraordinary ideas. - Frans Johansson, The Medici Effect

4) Coaching

Coaching benefits from your accumulated expertise and insights to guide others along their career journeys, especially for people taking a non-linear path. 

By drawing on your own experiences and lessons learned, and providing mentorship, you not only contribute to the development of individuals but also reinforce your own understanding and mastery of the different subjects or industries.

A growing number of people are transitioning to new kinds of work, and whether voluntary or involuntary, they can greatly benefit from the experience of someone who has navigated their own transitions.

Customizing a story of your career

As mentioned previously, recruiters and hiring managers are increasingly using pattern matching to manage the sheer volume of applicants.

To increase your chance of being interviewed and getting an offer, you’ll want to practice and highlight a narrative for your career that succinctly demonstrates how you are a good match for the opportunity.

To do this, you need to first step back and brainstorm several key elements.

• A passion or purpose that drove your career, and how it ties into the organization’s reason for being

• Problems you solved that are highly relevant to the opportunity

• Skills or expertise that you used that were core to solving those problems

• Impact that you created, that the organization would value

• How the intersection of your domains and disciplines make you powerfully suited to tackle the opportunity

Then use those elements to construct a narrative of your career, customized for several important conversations and formats:

• For asking someone in your network for an introduction, referral or reference

• For outreach to a recruiter or hiring manager

• To customize your cover letter and resume

• For informational interviews or first conversations with recruiters

Furthermore, if you make it far enough, you’ll want to use these elements for your interview preparation. Use them to customize a handful of case studies you can draw on to answer questions during your interviews.

Ultimately, we are in a “buyers market” for jobs: you can’t rely on hirers to connect the dots between the opportunity and your career. As much as possible you need to do it for them, because you’re the one that can look back and do so.

You can’t connect the dots looking forward; you can only connect them looking backward. - Steve Jobs

Cultivating a network of people who value your intersections

This may be the most important step you can take, though also one that takes the most time.

The goal is to activate a network of people who can send you opportunities and refer you to roles where you will be valued. In particular, you want a group of people that:

1. Understand the value of non-linear careers, because they have one themselves or because they have worked with people who have

2. Can see your non-linear career as a differentiator, and recognize that the intersections of different aspects of your career give you a super power

3. Are steeped enough in a domain that they can help you customize your career narrative and your offer to companies to work in that domain

As an example, I ended up working at Facebook in large part due to a referral from a fellow entrepreneur that could recognize the value my non-linear career offered and who was well positioned to tell my story to people within Facebook that mattered. Likewise, I was fortunate to be hired at Automattic by a leader experienced enough to see my potential (with her own non-linear career), but who was also connected to people in my network who could verify that value.

In contrast, here are a couple examples of feedback I’ve gotten from people that did not meet any of the above criteria:

• “You’re clearly experienced with product, but we don’t know what to make of everything else you have done.”

• “You probably like working on different things because you know you’re not good enough at any of them.”

If you don’t want to encounter the above, cultivate a network of people who understand that not all value comes from straight lines.

Not all those who wander are lost

I’ll close with this poem from J.R.R. Tolkien’s Lord of the Rings, a riddle which was given to Frodo by Gandalf to identify the real “Strider”, a ranger who had been wandering Middle-earth for years.

All that is gold does not glitter,

Not all those who wander are lost;

The old that is strong does not wither,

Deep roots are not reached by the frost.

From the ashes a fire shall be woken,

A light from the shadows shall spring;

Renewed shall be blade that was broken,

The crownless again shall be king.

Even Aragorn, Hero of the Fellowship and future king of Gondor, needed help to be recognized and for his wandering to be valued.

Like Aragorn, show the world you may have wandered, but you are not lost.

Considering tackling a turnaround?

A turnaround, whether it’s an individual team, product or a whole company, can be an incredible opportunity for impact and personal growth.

However, not all turnarounds are created equal, and you should make sure your own goals and personality matches what the situation requires.

And if not, feel free to say “thanks, but no thanks”.

In a recent Product Thinking podcast, Melissa Perri hosted Mauricio Monico (CPO of Wish) to discuss his experiences with product leadership and turnarounds at Wish, Indigo and eBay. 

I was particularly struck by his acknowledgement of how fortunate he had been to be part of executive teams that were already committed to change. 

“We had a lot of conflicts in terms of how to do it… But fighting the status quo was not a problem we had”

Having worked on a number of turnarounds and product reboots, as well as advising other leaders through them, I can tell you that level of executive commitment is far from guaranteed.

This lack of commitment can manifest even when the urgency of the situation is quite high, i.e. when there are strong signs that your product or business will be impacted soon, or is already being impacted.

Commitment vs. Urgency

When presented with the opportunity to take charge of a turnaround, you can take those two concepts—commitment and urgency—to shine a light on the likely conditions and the type of leadership required. 

And whether or not the opportunity is a good fit for you personally.

To do this, estimate the degree of commitment to the turnaround—from the company’s leadership and key stakeholders—on one axis of a 2x2 framework, and put the level of urgency the company is facing on another axis. Each axis ranges from low to high.  

Note, the level of importance or impact here is separate. You’re considering a turnaround because it matters to you or someone in the company.

Commitment considers the degree to which the company has internally rallied to address the importance, while urgency considers the more external factor of how soon your company will be impacted.

For example, imagine a company providing an SEO service that is observing the impact of Generative AI content on its business. Urgency is high if the company is already experiencing significant impact on its business, but is lower the further out into the future those impacts appear.

Using this framing, there are four extremes you can find yourself in, along with a different archetype that thrives in each:

I. Low commitment, low urgency / “Prophets”

Change is coming, and the business could be upended some day, but few stakeholders are concerned about it at the moment, often due to more pressing near-term priorities. 

Taking on a turnaround here is the land of “prophets”: people who have a deep belief in what’s coming, the capacity to tackle a problem that very few leaders in the company prioritize, and the ability to build the case for increased commitment. 

Take this on if you’re passionate about the domain/problem and if you have the endurance to work on building the case for an extended period of time with minimal support.

You may need to “keep a day job” while doing this, where you are addressing near-term priorities for the business to justify your employment. 

II. Low commitment, high urgency  / “Heroes”

Change is here, with disruptive impacts already being felt, but stakeholders are resistant to change and highly protective of the status quo. That protectiveness can be due to a variety of factors, often due to strongly established revenue or operations. Or a critical stakeholder is unwilling to change (founders, various CxOs, etc.) 

This situation requires “heroes”: people with a high risk tolerance—or who are protected from risk—because given the extreme urgency, they will typically have very few attempts to get it right. Meanwhile, the lack of commitment increases the probability for failure. There are fewer resources and potentially even people fighting to maintain the status quo. 

Only take this on if you believe the experience will be worthwhile even if you fail… because you might be made to fall on your proverbial “sword”. 

III. High commitment, low urgency  / “Pathbreakers” 

Change is further out on the horizon, but stakeholders believe its impacts are coming. How those impacts manifest is generally not yet understood, and despite the promise of investment, what exactly to invest in is not clear. 

This is the world of “pathbreakers”: people who are comfortable with discovering the path forward but also with building the structure for others to follow and the spaces to learn and grow. Also, high visibility tends to go hand-in-hand with high commitment, so continuously demonstrating progress towards the right path is critical… especially when the right path itself is not yet clear. 

Tackle turnarounds in these conditions if you are comfortable with high visibility roles where the way forward is unknown. You also need to be comfortable changing directions and demonstrating progress outside of standard metrics. 

IV. High commitment, high urgency  / “Maestros”

Change is already disrupting the business and stakeholders are committed to doing something about it, frantically so. You have limited time to find and validate new strategies, so execution and prioritization are critical. 

This is the realm of “maestros”: people with deep expertise in the domain, as well as ingrained intuition and creativity for potential solutions in that domain. The number of turnaround attempts are very limited, so leaders here also need the trust and authority to “conduct” the team or organization through a series of rapid, high-impact changes.  

Take this on if you’re comfortable with “the buck stops here” authority and accountability,  and moving rapidly with intention. Furthermore, as Mauricio advises “be very clear on what you're turning around from” as accurate understanding of the core problem is critical to the pace required.

If there are significant obstacles to obtaining such understanding, you may want to think twice.  

—

It’s important to note that the four examples above should be extremes, and you may find that your own scenario—or your own ideal—is somewhere more in the middle.

In my own career, I have also found this decision to be highly dependent on the company and my standing there. For example, I’ve successfully taken on a “maestro” turnaround at some companies, but wouldn’t consider it at others. Likewise with the other three roles. Consider the type of support and assurances you would want in each. 

In summary, turnarounds can be fantastic opportunities to upscale your impact and to learn rapidly, but do your best to evaluate if it matches the role and experience you will thrive  in.

Don’t minimize the importance of luck in determining life’s course. - Alex Trebek

I met my spouse after a chance encounter with someone that later introduced us. Even a 30-second delay would have meant me sitting next to a different person at that conference, a “sliding doors moment” leading to a totally different life. 

These kind of life-changing stories of fortune are common enough, but I think it’s clear to most people that blind reliance on fortune is still a mistake. Wise people don’t rush to play slots at a casino upon hearing about someone who had won big: the role of luck in winning at slots is too well understood. 

Nevertheless even with that common wisdom, I find people—myself included—often overlook how much fortune and luck contribute to our own success, as well as to the success of others. 

Like many people I know, I frequently catch myself comparing my achievements to others who have attained remarkable success. I strive to replicate their accomplishments, but underestimate or discount how unique the circumstances were that led to their success.

And as human beings, we love our deterministic narratives—hero X took action Y and created outcome Z—but the real world is much less certain and more probabilistic than we give it credit for, and the role of external factors is much bigger than I think most of us are comfortable with. 

Likewise, in the entrepreneurship world, successful ventures are highly studied and emulated, yet we still see a convincing majority of startups fail. This failure rate is remarkably stable, despite decades-worth of new methodologies and expert know-how that’s been developed and poured into the craft of venture creation.    

Chance and luck play a big role even here. 

But what can we do about it?

The first step is to account for chance and fortune when we study success, otherwise it is impossible to reliably learn from it… or to learn from failure.  After all, what worked for them won’t necessarily work for you, and what failed for others, might be the key to my own success. 

The second step is to make your own luck.

When I reflect on the most successful people I know—i.e. the people who can reliably recreate successful outcomes—I see people who are obsessive about “stacking the deck”.  

They look beyond the problem they are trying to solve, study the environment they are operating in and the factors that could influence success, and then they find and apply leverage to bend those conditions in their favor. 

Here are four ways in which they do so:

• Making the work worthwhile, no matter what the outcome is

• Developing an effective endurance strategy

• Deeply understanding operating context and structure

• Building capacity to generate opportunities

—Making the work worthwhile, no matter what the outcome is—

Choose to work on things that matter, something that will leave you or the world better off for having made the attempt.

For example, founder David Rogier was advised to work on an idea “that even if it fails, you would be proud of it”. Helping everyday people learn from experts was his idea that mattered, which became the core of MasterClass. 

Likewise, bestselling author Philip Roth is famously quoted as claiming “Nothing bad can happen to a writer. Everything is material.” For a writer, even failure can create opportunities. 

This is why passion for what you’re working on is so critical, but also creating ways to demonstrate and share what you have learned and to position yourself as a catalyst for others.

—Developing an effective endurance strategy—

I’ve written about the importance of endurance to innovation before, and the below applies equally well to making the most of fortune and chance.  

It takes time to build the capabilities and position to realize opportunities when they arise, either ones created directly by you or by external factors. To earn that time, you need an endurance strategy to not only keep your company “in the field” with the innovation, but to be ready to strike.

Want to be in the right place at the right time? You need to execute a strategy to allow you to endure long enough until you can find that right place, and to be ready to make the most of it when you do.

—Deeply understanding operating context and structure—

No effort exists without context, and that context creates constraints for what’s possible, whether it’s a brand new startup or a corporate innovation attempt. 

There’s a reason why both Uber and Lyft started in San Francisco, a city where it was practically impossible to find a cab. Likewise, if you’re a fintech startup, there are pros and cons to base yourself in a financial capital like New York, providing a context and constraints that could either boost your efforts or strangle them.

The point is to strive to deeply understand the context you’re operating in, so you can intentionally make a change to that context and its structure, pushing your boundaries to increase your chances of success. 

For example, the bestseller “Never Search Alone” outlines a strategy to change the underlying structure of a job search, by joining forces with other job searchers to improve your opportunities to find a new job.

—Building capacity to generate opportunities—

When something is new, quantity has a quality all of its own, specifically the quantity of opportunities you have to address real customer problems or to work meaningfully with a new capability.

Want to work on a new language learning service? Then figure out ways to maximize the opportunities you have to meaningfully engage language learners and educators, even before you’ve nailed down your solution. 

Ideally you can engineer a way to do this that both feels natural and is scalable, feeding a flywheel effect of feedback and innovation that becomes it’s own differentiation and moat. For example, Open AI built up a massive flywheel of feedback and innovation with the launch of ChatGPT, drawing in massive human engagement and training data that’s critical to the effectiveness of Generative AI services.

—

In closing, whether you are reflecting on success or failure, whether that’s somebody else’s or your own, don’t forget to consider the role that fortune and chance played. And when you’re starting something new, remember to do your best to engineer as much luck for your efforts as you can.

May Make luck be on your side.

May Make fortune smile upon you.

These two courses profoundly resonated with me, not only by deepening my understanding of LLMs but also by reinforcing two crucial management principles for innovation and navigating uncertainty.

I'll summarize the first principle as the 'Goldfish Principle'—assume a short memory and constantly manage context—and the second as 'Objective Benchmarking'—establishing effective measurement systems when facing uncertain opportunities.

—The Goldfish Principle—

One key concept from these courses is the understanding that LLMs are inherently stateless. While LLMs excel in natural language processing and understanding context, this context is confined within a limited 'context window.'

Picture a wise goldfish with access to all human digital knowledge but only a 3-second memory span*.

With a goldfish-like memory, managing context is therefore a critical task in LLM application development: how do you continuously supply the LLM with the right context, given that it is constantly updating due to user actions or environmental changes?

This task is not only crucial in LLM development but also in innovation in general.

Effective leaders excel at supplying and managing context, especially when venturing into the unknown. It's essential to provide clarity on what, why, and the progress made, particularly in novel situations where multiple perspectives are invaluable.

Managing context is equally crucial when working alone to prevent losing focus or sight of the bigger picture.

In summary, the Goldfish Principle prompts us to envision our organizations like goldfish or LLMs with limited memory and systematically manage context for ourselves and the organization.

—Objective Benchmarking— 

Another key property of LLMs is their inherent probabilistic nature.

This non-deterministic and non-linear aspect of LLMs makes them adaptable to diverse tasks, but also comes with challenges.

Essentially, using natural language, with LLMs you have you have almost an infinite number of responses you could prompt for. Contrast that to a more deterministic technology, like a relational database, where you are constrained by the query language and structure of the database. 

However, with a badly formed database query you’re likely to trigger an obvious error. With LLMs you could just get nonsense in response. 

Or something that’s genius.

Evaluating which outcome an LLM  is creating, nonsense or genius, and doing so at scale, is another core task in LLM application development. 

Similarly, innovation efforts operate in a non-deterministic world, where outcomes are uncertain. You can’t get enough data yet to determine likely outcomes, but you may be facing a seemingly infinite number of paths you could try.

So like with using LLMs, you need a mechanism to determine if you are progressing towards your goals, in a way that is comparable and informative. 

This is where objective benchmarking comes in, i.e. a system of evaluation criteria and tests to measure how well your application or organization is performing against relevant tasks or goals.

For an LLM that often begins with using human feedback and sense checking, but then graduates to using already established benchmarks or other AI models to evaluate the LLM’s effectiveness. 

Likewise for innovation efforts, defining benchmarks based on human feedback is a great place to start, especially for the early stages of defining the problem and determining viability. 

For example, if you think you might have a solution to improve math literacy in inner cities, what kind of feedback would be convincing enough to experts on the subject?

Capable of proving you are on the right track? Or just as important, to tell you that you’re heading in the wrong direction?

Just make sure the human feedback is objective, relevant and convincing.  You are looking for a strong signal to guide you, not emotional validation for your idea. 

—Summary—

In my experience, embracing these two principles—managing context [for a goldfish] and objective benchmarking—lays a solid foundation for navigating uncertain opportunities. 

Teams and organizations that prioritize these principles often excel, leveraging them to thrive in unpredictable environments. Conversely, those who neglect context and benchmarking tend to encounter unnecessary obstacles and setbacks, hindering their ability when facing the unknown.

[* Turns out the whole “3-second goldfish memory” belief is a myth, but it works for this analogy so I am sticking with it]

When it is not in our power to follow what is true, we ought to follow what is most probable - René Descartes

If you work as an entrepreneur or innovator—or someone creating or responding to something new in the world—then you face a fundamental truth.

Uncertainty abounds. 

It took me 20+ years working on new ventures to internalize this truth. Also to learn that when creating something new, much of what determines success is outside of our control. Almost nothing is certain, the outcomes we seek are—at best—just probable. 

Our job is to make them more probable. 

I am starting this newsletter to write about experiences and lessons with building products and ventures, from my career as a product builder and business leader, as an entrepreneur and corporate innovator, both in and out of the tech world. Some lessons I have already learned, but many I’m still learning. 

The central theme is exploring examples and methodologies for taking an idea or goal that isn’t real yet, with a near 0 chance of being true, and transforming it to probable. 

Turns out that when nothing is certain, probable is your best friend. 

My journey started as a software engineer at Apple and Rockwell, developing new technology and translating AI research into real-world applications. After getting an MBA in Sustainable Enterprise, I went on to lead SC Johnson, Duport, Ascension Health and other companies in launching new ventures in Kenya, India, Ghana, Brazil and the U.S. Then it was working on several startups (including my own) and breaking ground on new technology products at Facebook and Automattic.

Throughout, I was frequently drawn to the early stages of products and ventures, and found myself facing a recurring series of questions.

• Is the problem I want to solve real? How can I build the skills I need, and will I be able to attract the resources and people I need to succeed? 

• Is this opportunity right for me? How can I make this worthwhile even if it fails?

• Can we win enough time to build an effective solution? Will people value what we develop? Enough to earn what it costs to make and to grow?  

• Will our strengths and advantages materialize, or will competition or competing priorities derail us before we can even prove ourselves?

• Will we time the market right, or will someone else reap the benefits of what we proved?

• Will we actually create the change we seek in the world?

At the heart of all those questions is uncertainty, and over time—after many mistakes—I learned the importance of a probability-based mindset to tackle that uncertainty head on. Yes, effort, experimentation and ingenuity are important, but so is working to “stack the deck” with structure that maximizes your probability of success. 

By “structure”, I mean systems that support you with outcomes like:

• Picking the right problems for you to work on

• Learning what you need to know quickly and effectively

• Getting setup to take “shots on goal” and enabling you to endure long enough to take as many as you need

• Positioning you and your efforts to best attract resources and customers

• Determining whether your desired outcomes are becoming more [or less] probable

• Ensuring your work is worthwhile, even if you fail

To use an analogy, if your venture is an aircraft, then structure is like a carrier that enables it to reach new places, with a hangar that allows you to equip your aircraft for new journeys. 

With Probable Wisdom I’ll be publishing articles about what I’ve learned to adopt a probability-based mindset, as well as lessons from more than two decades as an entrepreneur and innovator. Most of all, I’ll be using this newsletter as my own “carrier” on a personal learning journey to make “probable” a best friend to build something new. 

Please join me on this journey.

“When it is not in our power to follow what is true, we ought to follow what is most probable.” - Renee Descartes

Articles and lessons from more than two decades as an entrepreneur and innovator, particularly about adopting a probability-based mindset for product, venture-building and your career.

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