Playbook for navigating career transitions

I’ve made 3 career transitions in under 6 years. I’ve thought a lot about how to maximize success and minimize sleepless nights during these moments of change. They are the personal equivalent of: “there are decades where nothing happens, and weeks where decades happen.”

How best to navigate them?

Waste no time in pursuing the new thing
Figure out the skills you need
Bridge the gap as quickly as possible

That’s the conventional playbook. Sadly, following convention often leads you straight to the boulevard of broken dreams.

To avoid these traps, I came up with a new playbook:

Identify relevant strengths
Estimate distance to your destination
Find an “in”
Trial your new role
Get gatekeepers to say “yes”
Take small steps that ladder you up

I’ve pressure tested this on my transition from consultant to PM, and my most recent transition from PM to solopreneur. But there’s no better test than to share it with you.
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Identify relevant strengths

Before you do anything, map out the overlap between your existing toolbox and your new toolbox. There’s often a surprising number of transferable skills that set you up for success.

When I was transitioning from consulting to PM, my painstaking practice of analysis helped me identify product opportunities. My endless hours of crafting PowerPoint headlines helped me get to the “so what” faster, and earn credibility with others.

Some of the best PMs come from wildly different backgrounds. All of them have figured out how to turn the strengths honed in past lives into superpowers. Knowing what that could be for you helps convince yourself and others to take a leap of faith.

Similarly, when I first dreamt of leaving the corporate world, I knew I needed to learn how to build an audience. For someone who rarely posted on LinkedIn, only lurked on Instagram and didn’t even have a Twitter account, this was a daunting challenge.

So I turned to a relevant and comfortable strength: writing.
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Estimate distance to your destination

Reflecting on your relevant strengths also gives you an honest signal of the distance you need to cover to get to where you want to be.

The real value of this exercise is to temper your own expectations. If you have limited strengths that apply to your new role, the road is not impossible, but it will be long. Ask people who are doing what you want about the steps they took, and how long it took them. If you don’t know anyone who’s done it, that’s another sign you’re in for a steep and probably lonely trek.

Having realistic beliefs is the first step towards persevering. Know the price tag, then decide whether it’s worth paying.

When I started writing, I expected growth to be slow. The internet is awash with content, and it takes a lot of practice to say things that are worth people’s time. I was not disappointed when I did not become an overnight sensation. I knew the distance, but I was having fun discovering new thoughts simply by putting words down.

This is the true value of doing things that are play for you, and work for others. You enjoy the game, forget about keeping score and end up benefiting from the magic of compounding.

Not everything you need to do will fall in your “play zone”. This means setting directionally realistic expectations is even more important.
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Find an “in”

It’s easy to be trapped by desperation. When you have no experience, you should say yes to any opportunity, right? Only if you can easily undo said opportunity.

Most career transitions are not cheap. If you plan on spending at least a year with a company, you should do your best to know what you’re getting yourself into.

You have the highest chance of success at a place that values your strengths.

For example, there are many ways to build a great product. Some teams lean on technical excellence, others on awe-inspiring designs or a business-driven approach.

Assess the type of team you’re dealing with by asking: Who decides what to build? How are they made? Who breaks the tie during a stalemate? It can also be inferred by the backgrounds of the people who lead the product teams.

I wasn’t technical or a design savant. But I did have an analytical mind. Faire was a great fit for me because the business model is complex, and the founders are very data-driven. Getting the numbers wrong by a little cost the business massively, so people who could break down and move metrics were respected.

You’ll always need to pick up new skills, but you gain a powerful edge when you start from a foundation of strength.
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Trial your new role

Progress comes from doing the real thing. But the real thing may not need to be a huge commitment outright.

Many people clamor to be PMs, but few people bother to talk to customers and look at metrics. You rarely need permission to practice the craft. Take stuff off people’s plates to get a taste for what you think you want. De-risk the next few years of your life.

Before I left my PM job, I published every week for 7 months to see if writing could be an enjoyable part of going independent. It’s now easily the favorite part of my week. Giving this a long trial run gave me the confidence to invest further. I’m now thinking of ways to turn a growing archive into a useful library of resources, but all of this started as a tiny experiment.
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Get gatekeepers to say “yes”

Gatekeepers are an inevitable part of every career transition, from hiring managers to promotion committees and even customers!

You unlock a whole new universe by understanding the hurdles to “yes”. To illustrate, here’s an example of hurdles for consultants transitioning into PMs:

You get numbers, but do you get customers?
You get clients, but do you know customers ≠ clients?
Do you understand what makes a great product experience?

Hurdles form when the playbook for success differs between arenas.

Most consulting projects involve numbers, but very few get into the hearts of customers. Consultants also generally do whatever the clients ask because clients pay based on a desired output. Customers, however, care more about outcome. This requires PMs to imagine solutions on behalf of customers.

You need to find ways to overcome the hurdles to “yes”.

The same applies to converting customers. The most effective products directly address customer concerns, turning “why should I say yes?” to “how could I say no?”

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Take smaller steps

Many coveted transitions are a long distance plus a big leap.

I did market research and product analytics long before I PM’d anything. I shipped hundreds of tiny features before I worked on massive multi-month projects. Most of the time, I was taking small steps. But small steps day after day compounded into giant leaps over a few years.

Much of progress is only visible looking back. The leading indicator is consistent steps forward.

Since I shared my departure from the corporate world, I’ve often been asked: what’s your long-term plan?

When I justified leaving my PM job, I told myself that I wanted to start a business like Basecamp or ConvertKit. Profitable software that focus on making customers happy instead of flirting with investors. But I quickly realized I have a long distance to go before I’m even remotely close to that territory.

Rather than jumping straight into building something I don’t care about, I’m taking small steps and exposing myself to more problems.

I’m staying flexible on the details, and most importantly, savoring what gives me the most energy: writing and sharing everything I learn.

Thank you for the opportunity to do what I love!
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Consultant, PM, Solopreneur