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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If you want to wait until you’re perfectly “ready” to start a company before taking the leap, it will probably never happen.
While this is an often-repeated truth, that blanket statement dismisses the fact that there are ways that aspiring founders can and should make sure they’re mentally prepared for the journey ahead.
I don’t regret anything about my first startup experience – it came with a lot of hard lessons I needed to learn early in my career. But I can say that I was not mentally ready to start a company. I sourced a disproportionate amount of my self-worth from work (my startup), making me both a worse operator as I sought positive reinforcement to maintain my self-worth, rather than seeking hard truths. Because I was not ready, my 4-year founder experience took a mental toll that took a while to pay back.
As I think about my own desire to start another company and as I help other aspiring founders navigate the same, it raises the question: what does it mean to be mentally ready to start a company?
This is a question that jaded or burned out former founders need to answer before getting in the ring again, but it’s also a question that first-time founders should consider, even if they think they’re ready.
I spent some time this week talking to friends who are currently founders or previously founded companies to try to answer this question. The three trends that emerged were (1) Durable self-worth, (2) Support systems, and (3) Obsession and energy.
Having a strong sense of self-worth is a foundational part of our well-being. It’s natural for founders to source some of their self-worth and identity from their startup.
But if you start a company, the most probable outcome is failure.
Needing your startup to be successful to give you self-worth is like playing blackjack with your life savings – while it can sometimes work, it’s highly likely that you’ll lose part of your financial foundation.
Survivorship-bias-fueled stories of famous entrepreneurs tell us that we have to pour every ounce of our identities into our startups. A lot of first-time founders (including my former self) make this mistake. This is fueled by shitty tweets like this:
Diversifying sources of self-worth outside of work and your startup ensures that if things aren’t going well with your startup, your self-worth can remain high. In other words, your self-worth is durable and can withstand failures, long periods of delayed gratification, and high levels of ambiguity. On the other hand, if your self-worth is over-leveraged in your startup, then these things which are inevitable – failures, delayed gratification, and ambiguity – can cause your self-worth and identity to erode quickly, in turn making you a worse founder.
Cultivating diverse sources of self-worth outside of work not only prepares you for the inevitable adversity of building a company, it makes you a better founder.
I texted a current founder friend, asking her, “what does it look like to be mentally ready to start a company?” She said:
So I don’t think there is any “ready.” I think that it’s wrong to think that any maturity level protects you for the hardship or guarantees success. Your mental and emotional well-being is always a work in progress. There’s not a steady state.
She went on to share some challenges that she and her co-founder had to deal with in their personal lives during the first year building their startup – things that they could never have anticipated happening which had nothing to do with the startup.
It reminded me – life doesn’t stop happening just because you’re building a startup and dealing with extreme levels of stress and ambiguity. Death, birth, illness, new relationships, breakups, and challenges with friends and family continue to happen while you’re a founder.
Dealing with the stressors of startups in addition to the challenges in life requires that we have support systems in place.
When I asked a former founder how he thought about what it looked like to be mentally ready to start a company, he said:
“Feel safe – recognize there is a lot of ambiguity ahead. When I say safe, I’m referring to the human relationships around you (work and personal). Know your [life] partner is committed to the process (and relatively bought in); know your co-founder relationship is a safe place.”
But support systems don’t need to stop at the personal relationships he described. After my first startup, I made a commitment to myself that next time, I would think about my partnership with a therapist through a similar lens as a partnership with a co-founder or early investors. Personally, I view that type of commitment a mechanism to ensure continued work on mental health throughout the startup lifespan. It’s not enough to be mentally “ready enough” on day 1 – you need to fortify your resources which will help you navigate the ambiguity and mental strain of building a startup on an ongoing basis.
Obsession and energy
Durable self-worth and Support Systems fortify your mental defenses for the challenges of building a startup. But those alone are not sufficient to make a founder ready to overcome the inertia of taking the leap.
One of the consistent responses I got from founders was around obsession and energy:
Be obsessed, not interested. Be energized, not drained. Be nervous, but not fearful.
The project/company has to be the thing you WANT to fill every open time slot in your calendar (this can/would turn into actually figuring out how to fit in a lot of time on it). It also should be the #1 thing on your mind — day dreams, planning, constantly jotting down random ideas/notes about it.
The best state of mind to start a company and from founders I’ve observed is that they are intellectually curious about another problem or opportunity they learned through work or a passion project. This problem haunts them, as either a personal infliction or a professional ideology. And they get to an impasse emotionally where they prioritize this problem over the mundane problems they deal with at their day job.
So how do you get obsessed with something?
It comes down to having energy to devote to things and giving yourself time to let obsession build.
Several experienced entrepreneurs I’ve talked to have advised me to “spend your time in ways that are net-energy producing.” While that seems obvious for living a happy life, I also see now why that’s so essential for getting ready to start a company.
It’s hard to become energized by or obsessed with something if you’re constantly at an energy deficit. A prerequisite for developing obsession is having the energy reserves to explore something outside of your day job (or if you’re lucky, have your obsession and your day job overlap with a personal flywheel). If your day job is draining, it’s going to be difficult to develop enough energy or obsession for anything else.
Assuming you have the energy to cultivate obsessions, founders also need time for that obsession to grow – it doesn’t happen all at once. This is especially true if they are recovering from a past experience.
After dealing with failure, I can say that I became jaded and did lose the obsession around company-building. So when I think about being “ready”, I think more about regaining the obsession. I can feel the obsession coming back. Slowly. But it’s coming back. I’m day-dreaming about company-building again. I’m reading startup/tech content, whereas for a while I would often feel bitter or dismissive towards it.
So when you’re thinking of starting a startup, while the idea and founder/product/market fit matter – none of it matters if you’re not personally ready for the journey ahead.
A comment around the "self-worth" idea: I've found this to be one of the benefits of continuing to do a little consulting work as I build my startup. It brings in income, yes, but almost as importantly, I'm doing something that makes me feel completely competent. So much of being an entrepreneur involves learning and stretching beyond the point of comfort, and it can be a nice counter-balance to have a little ego boost once in a while.