You're moving on from your startup. Now what?

A framework for navigating to the next chapter of your career after moving on from your startup, with reflections from my own experience.

May 9, 2021

Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes frameworks, analyses, profiles, and musings about building entrepreneurial careers. This isn’t just startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal.

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February 2018, I had just made one of the hardest decisions of my life – to give up trying to make my startup work after almost four years of grinding and raising $1M in funding. After that decision, I felt what most founders feel after deciding to move on from their startups: relief.

But that relief was short-lived. Once I’d made the decision to move on from my startup, I was confronted with a new existential question: what now?

I had less than $1,000 in my bank account, $60,000 in student loans, and lacked confidence in my competence and judgement after having spent years working my ass off with nothing to show for it. I was jaded about being a startup founder. I had no idea what I was good at or what I should do next. I was scared about how my career was shaping out.

Fast forward three years later, I’m 2.5 years into my tenure at Amazon where I’ve had a pretty fast trajectory, I’m out of debt, I’ve helped thousands of founders through my writing and workshops, and I’m well-positioned to start another company in a few years if I want to.

If I could tell that version of myself in February 2018 where I’d be now, I’d probably break down crying out of relief. Through a combination of luck, self-inquiry, and patience, I went from having no clue what to do next, to having a career trajectory I’m excited about.

It took me 8 months between winding down my startup and joining Amazon. There were some things I did well with that transition, and some things I could have done better. For founders who are moving on from their startups, this is the framework I would give my former self on how to navigate life post-startup and find the next chapter of your career. It breaks the process into five parts:

Get healthy and financially stable
Build community around yourself
Crystallize your entrepreneurial assets
Identify the assets you need to build in your next chapter
Hypothesize ideal options for your next move and inexpensively test

Cheat Sheet (TL;DR)
The rest of this post is a 13-minute read. Here’s an actionable cheat sheet of all of the questions you should be asking, which are explored in more depth in the post.
1) Get healthy and financially stable
What is the maximum amount you should be working to give yourself the space to recover?
What self-care practices do you need to establish?
What are the most lucrative, easy, efficient ways you can make money that aren’t energy-zapping and will give you a sense of achievement?
2) Build community around yourself
Who in your life cares about you independent of your startup, and how can you start reinvesting in those relationships?
Through your network, where can you find other founders going through similar transitions, and how can you start providing peer support to each other?
Who are former founders who moved on from their startups, who have a subsequent career arc that you admire?
3) Crystallize your entrepreneurial assets
What valuable relationships will start to decay if you don’t do something to crystallize them now, and what can you do to solidify them?
What skills did you develop or unique experiences did you go through which you think others could benefit from learning from? What’s the best way for you to crystallize and deliver those learnings to others so that you can get value from those assets for years to come?
4) Identify the assets you need to build in your next chapter
What assets (network, audience, skills, domain expertise, experience) are you lacking, which if not acquired, will undermine your career trajectory?
Assuming you want to start another company in the future, what assets (including financial assets) would you need to acquire in your next chapter in order to be ready to give it another go?
What assets would you like to acquire in your next chapter which would accelerate your career in the right direction?
5) Hypothesize ideal options for your next move and inexpensively test
What do you hypothesize are great next opportunities?
What are the most inexpensive ways to validate or invalidate those hypotheses?
Do you feel like you’ve learned enough about your initial hypotheses to initiate a well-run job search that could have you starting your next gig in 2 months?

1. Get healthy and financially stable

When I made the decision to wind down my startup, I was 15% overweight and mentally exhausted. I also had less than $1,000 in my bank account, credit card debt and student loans with mandatory payments, and other living expenses. I had relationships in my life that I had neglected and needed nourishment. I found myself in the difficult spot where I really needed a break, but couldn’t afford to take one.

After 3.5 years of not taking great care of myself, I knew that self-care had to be the top priority. The most important thing I did after deciding to wind down was setting immutable constraints: (1) I would continue seeing a therapist, (2) I would work no more than 30 hours per week to make sure I had enough space to recover, (3) I would join a gym and exercise daily.

Making those commitments gave me confidence that as long as I didn’t violate those constraints, I would get healthy and be able to figure out my next chapter from a position of stability.

I then found freelance work with those constraints in mind. At first, I didn’t worry about freelance gigs that would help me find the next thing. I just wanted to find the most effortless, lucrative freelance gigs I could find so that I could find financial stability and peace of mind. For me, that ended up being a few gigs which were pretty effortless given my previous startup (a marketplace where you could hire freelance web designers). I ended up working 15 hours per week for a freelance-economony-focused startup, while taking on selective web design projects that came in as inbound from my startup (which was a web design marketplace).

Picking gigs that I knew I could do well also helped me rebuild my professional confidence. At that point I didn’t need to learn new skills and stretch myself – I needed to pay my bills and feel a basic sense of accomplishment in the wake of my biggest professional failure. These gigs were really easy, and combined with my self-care commitments, helped me get healthy and find financial stability.

When moving on from a startup, everyone is going to be in a different place, but it’s important to start with what constraints you need to set to take care of yourself before thinking about how to find financial stability.

Questions to ask:
What is the maximum amount you should be working to give yourself the space to recover?
What self-care practices do you need to establish?
What are the most lucrative, easy, efficient ways you can make money that aren’t energy-zapping and will give you a sense of achievement?

2. Build community around yourself

They say that being the founder of a startup is an incredibly lonely experience. But you know what’s lonelier? Being that same person but without the startup.

One of the most important things to do when moving on from the startup is bolster yourself with community. There are types of relationships worth investing in right away: (1) personal relationships, (2) other former founders going through a similar transition, and (3) former founders you admire who are well into the next chapters of their career.

Personal relationships

While building your startup, founders build relationships that are predicated on the startup itself – employees, investors, co-founders, customers and partners are all relationships that a founder might build over the lifecycle of their startup. But without the startup, some of those relationships can dissolve or become strained. It’s important to go back to the basics and reinvest in the relationships that existed without the startup – the people who care about you independent of your startup. Giving and receiving love in these relationships can be restorative, as they’re a reminder of a former founders’ worth outside of their startup.

Other former founders going through a similar transition

Moving on from a startup is a really challenging experience, and few people can empathize with that experience. Finding other founders who are also moving on from their startup can provide many of the benefits of a support group – relating personal experiences, providing support to one another, and connecting each other to useful resources. When I was going through this transition, I had a group of 3 other founders also moving on from their startups (one of which was my co-founder) – we helped each other with accountability, passed each other freelance gigs, and occasionally talked about the challenges we were dealing with. This was so valuable that if I could go back in time, I would have invested in it more. I would have found more founders going through a similar transition and created a more formal support group.

Former founders you admire professionally

There are a lot of people who have had to move on from their startups over the years, many of whom are now thriving in their careers. Not only can these people relate to the challenging experience of moving on from your startup, they can give you a glimpse into what navigating the future looks like. Finding and building relationships with people like this who you admire professionally will give you a sense of what it looks like to chart a course forward, reassurance that things will be ok, and give you some ideas about what you could do next. These former founders remember how difficult it was, and are generally very generous in offering their time to other founders who’ve been in the arena.

Questions to ask:
Who in your life cares about you independent of your startup, and how can you start reinvesting in those relationships?
Through your network, where can you find other founders going through similar transitions, and how can you start providing peer support to each other?
Who are former founders who moved on from their startups, who have a subsequent career arc that you admire?

3. Crystallize your entrepreneurial assets

As soon as you move on from your startup, the assets you accumulated while building your startup – relationships with investors, skills as an operator, unique experiences as a founder, and everything in between – will start to decay.

That’s why it’s valuable to take inventory of those assets that you’ve accumulated and figure out how you can crystallize them so that you carry them with you into the next chapter of your career.

You see some founders do this through post-mortems, where they’re able to take their experiences where the startup failed to crystallize their expertise on the space they were building in. These post-mortems serve as durable artifacts that can help founders build relationships with investors and other founders who are interested in that space.

Other founders take the time to crystallize the relationships they’ve built with investors. They may start sending deal flow to their investors or start helping their investors with due diligence on other companies – both actions that solidify the relationship beyond the life of the startup.

For me, one of the most valuable things I did was write a book on fundraising with a friend whose startup also had failed recently. Writing a book on fundraising took the good and bad fundraising experiences we had as founders and crystallized it into an asset that has been a force multiplier on my career trajectory, which I explained in my post, side projects as a lever for professional growth:

By most measures, the book isn’t all that successful. It doesn’t receive any press or notoriety and we haven’t made any money on it (though it has been read a couple thousand times).
But being able to say that I wrote a book on fundraising that lots of folks have read created qualifications and credibility out of thin air.
It gave me just enough startup credibility to join the Startup team at AWS. As a 28-year-old trying to build trusting relationships with successful entrepreneurs and investors who ran accelerators and incubators, it gave me a higher starting point for credibility, which facilitated the rest of my job. Six months into my tenure, when AWS needed someone to do a presentation on seed stage fundraising, I was among the most qualified people on the team to create one (which was essentially just the cliffnotes of the book).

In your next chapter, you may end up building on the assets you’ve already accumulated in your last startup. But you should not count on it. I’ve seen founders who don’t crystallize their assets fall victim to the sunk cost fallacy. They feel like they need to continue building on the assets they’ve built and stay in the same space as their startup so that those years don’t feel like a waste. Crystallizing these assets allows you to preserve them, so you can think about your next chapter with clear eyes and a fresh piece of paper.

Questions to ask:
What valuable relationships will start to decay if you don’t do something to crystallize them now, and what can you do to solidify them?
What skills did you develop or unique experiences did you go through which you think others could benefit from learning from? What’s the best way for you to crystallize and deliver those learnings to others so that you can get value from those assets for years to come?

4. Identify the assets you need to build in your next chapter

As I wrote in my power Everyone is an Investor, one of the ways for entrepreneurs to maximize the output of their careers is by building entrepreneurial assets (network, audience, skills, domain expertise, experience). When thinking about what’s next, it’s important to think long-term about your career and the assets you want to build in your next move. There are three ways to think about the assets you want to acquire: (1) risk mitigation, (2) upside opportunity, and (3) required assets for the next venture.

Risk mitigation

What assets are you lacking, which if not acquired, will undermine your career trajectory? For me back in 2018, the answer was clear: I’d spent my entire career to that point working for fledgling startups (either someone else’s or my own). I didn’t feel like I knew what operational proficiency looked like, and I had not worked for any companies that anyone would have ever heard of. In order to de-risk that, I needed to join a company where I could (1) learn what varsity-level operations looked like, and (2) show people that I’ve worked for a reputable company. That ruled out opportunities at seed-stage startups, as I needed high confidence that my next employer would be both operationally proficient and reputable. Finding an opportunity that met those criteria would address biggest risks that could undermine my career, providing some downside protection for my career trajectory.

Upside Opportunity

What assets would you like to acquire in your next chapter which would accelerate your career in the right direction? When building entrepreneurial assets, it’s worth thinking beyond downside protection. You can think in the future and think about the network, audience, skills, or domain expertise you want to build which you believe will set you up for the trajectory you want. I was less clear about what I wanted here when I was navigating my next chapter, but I knew if I could build assets in the world of startups, I would be accelerating my career in the right general direction.

Required assets for the next venture

Assuming you want to start another company in the future, what assets would you need to acquire in your next chapter in order to be ready to give it another go? Entrepreneurial careers are long and require getting shots up. If you want to start another company, you should be honest with yourself about what you’d need before doing it again. For some people, that mean they take an easy job so that they can have enough time to rest and and work on side projects. For others, that might mean having specific financial goals you need to achieve before you’re ready to give it a go.

For me, the needs were clear: I needed to eradicate my debt, build a financial safety net, and build a healthier relationship with work (I’m two for three).

Questions to ask:
What assets (network, audience, skills, domain expertise, experience) are you lacking, which if not acquired, will undermine your career trajectory?
Assuming you want to start another company in the future, what assets (including financial assets) would you need to acquire in your next chapter in order to be ready to give it another go?
What assets (network, audience, skills, domain expertise, experience) would you like to acquire in your next chapter which would accelerate your career in the right direction?

5. Hypothesize ideal options for your next move and inexpensively test

As you go through this process, you should start hypothesizing ideal options for your next chapter. Rather than jumping into the job-search process, you should first find ways to inexpensively test the hypotheses that these direction might be the right option for you.

For example, I hypothesized that going into VC would be a good next step for me. I ended up inexpensively testing this by freelancing for VCs to learn what that experience could be like, while getting paid. I quickly learned that I didn’t enjoy being on the investor side and vastly preferred being an operator. This was a much more cost-effective, two-way-door way of testing my hypothesis than jumping into a role in VC or committing to an internship that would eat a lot of my time.

Other ways of inexpensively testing these hypotheses about your next chapter include coffee chats with people who have those careers, doing informational interviews, taking on freelance gigs that would emulate the day-to-day, and working on side projects in those spaces. Much like when building a startup, you should be testing your hypotheses as inexpensively as possible, and as you learn about where you’re wrong, your hypothesis will become more and more well-informed and nuanced.

It’s important to be cognizant of whether you’re (1) hypothesizing and testing what could be the right next chapter, or (2) actively job searching. Much like fundraising, a job search should be run with a well-oiled process (this is a great post from Mike Tarullo on how to run this process). There’s a difference between being in the hypothesis-testing stage and the actively-job-searching phase. Once you feel like you have some confidence around the types of next opportunities that you feel meet the needs of everything discussed in this post, you should turn on the job-search process. A good litmus test to know when you’re ready to enter that phase is asking yourself, “Do I have high conviction that I’d be ready to start one of these jobs in 2 months?”

Questions to ask:
What do you hypothesize are great next opportunities?
What are the most inexpensive ways to validate or invalidate those hypotheses?
Do you feel like you’ve learned enough about your initial hypotheses to initiate a well-run job search that could have you starting your next gig in 2 months?

Starting a company is incredibly hard. Moving on from it is even harder. The last thing founders want to deal with after deciding to move on is more uncertainty, but unfortunately that’s what they’re faced with when trying to figure out what’s next.

It’s tempting to try to avoid that uncertainty and jump into the next thing quickly. But the transition from a former founder to the next chapter of a career can be far more than a soft landing – it can be a springboard.

Using that founding experience with a less-than-great outcome as a springboard requires intention, self-inquiry, patience, and continued comfort with discomfort. But it can all be worth it, and it get you on a strong career trajectory that will position you well to start another company in the future.