The emotional state of an entrepreneur

Bayes' Theorem, which expresses how a subjective degree of belief should rationally change to account for evidence. Img via  Matt Buck - Flickr  |    CC BY-SA 2.0

Bayes' Theorem, which expresses how a subjective degree of belief should rationally change to account for evidence. Img via Matt Buck - Flickr | CC BY-SA 2.0

Entrepreneurship is largely about belief.

Sometimes that belief is what keeps us going, but it can also lead to dangerous territory — like listening mostly to people who think the same things we do, or shelving deeper feelings for years only to find out later that they are subconsciously undermining our best work. 

A common mantra in the startup ecosystem (besides hustle, scale, and growth) is that you should test your assumptions. There are different approaches to testing, including the well known lean startup method that Eric Ries advocates for. It’s a concept that’s also well covered by Steve Blank, Seth Godin, and an array of designers, technologists and thinkers. 

With the exception of Seth, most of the time the language / framework for testing assumptions is focused on developing & designing a product or learning from customers, and rightfully so. As soon as an idea gets out of your head, into the real world, and beyond a small circle of people… that’s when challenging your assumptions becomes critical. 

But there’s another, slightly different way of thinking about it: you’re testing what you believe to be true, not only about your product but about yourself. 

Nowhere is this more evident than in how we avoid, deal with, process, or even embrace our emotional state in times of turmoil, whether it happens quickly or over a long period of time.

Much of Westernized culture encourages (and sometimes demands) that we see being stoic / stuffing down feelings / refusing to show our inner self as the ultimate expression of control, power, and independence. Some of this may be biologically a part of the human experience via evolution, though that is a much larger topic for another time and a different place. 

A friend of mine calls this phenomenon being Wired For Struggle. For entrepreneurs this can be expressed in multiple ways, including overconfidence, lack of confidence, anxiety, depression, and imposter syndrome.

Solving for the roots of Wired for Struggle has a lot to do with what we believe about ourselves, what we think we are good for (or not), and whether we are willing and/or able to embrace the things we most fear. 

MOZ founder and CEO Rand Fishkin shared an honest and difficult story several months ago about some of these things (his conversation with Jerry Colonna on the Reboot Podcast is a good one, too). There’s also a piece by Brad Feld about founder suicides, to which Kyle Wild responded with some thoughtful notes on the relationship between entrepreneurship, depression, and a culture of overwork. All are worth reading / listening to. 

But what’s really stuck in my brain for the last few months is something Erica Baker said back in December, on Medium:

In the piece, which is worth reading in its entirety, she shares what it feels like to be one of very few black women working in the tech industry. Among the intellectual and emotional complexities she faces: a pressure to fit into a culture that both asks her to represent people “like her” and simultaneously ignore race and gender, constant micro-aggressions that reflect institutionalized -isms, isolation, and a low level stress / anxiety that never quite goes away. 

Embedded in her (and Rand’s) story is a nuance about belief: often we are most in danger when we internalize stories that we haven’t had a chance to test, or examine. In Erica’s case this is especially tricky because a lot of what she’s forced to look at or deal with has nothing to do with her, it’s the result of decades of institutionalized bias towards two categories of human that she just happens to be in. 

*To be clear: I don’t believe it’s her job to fix racism or sexism in the tech industry, or to explain how it works to anyone. I believe it’s her job (as it is for all of us) to figure out for herself what will enable her to become a whole human / have a meaningful life. 

But what it made me think of is that when all we know how to do is drown or fight unexamined belief about ourselves (whether internally or externally imposed), that’s when we’re in rough territory. 

Brad Feld touched on this same idea in a post from a couple of days ago where he described working through depression:

Dealing with the particular set of demons in my cave at this point [took] another three months. That period was my second of three clinic depressions that ended around my birthday on December 1st. I spent these three months sitting with all of my demons, welcoming more into my world, and just learning from them.
When the really scary ones showed up, I didn’t fight. I just placed my head gently in each of the scary demons’ mouths and said “eat me if you wish.”

That embracing or acceptance that Brad talks about can be the scariest thing in the world for an entrepreneur…but it can also be a source of great strength. When we test beliefs about who and what we are good for, by extension it becomes a part of the product / company we build. 

Placing my own head in the demon’s mouth involved a different set of grief — a little under four years ago my mom died of ovarian cancer, the same year that I went through bankruptcy and divorce. There’s a lot more to that story, but one of the critical and still remaining threads there has to do with how I began to believe that maybe I wasn't good enough, that I deserved to be isolated. I breathed in the anger, sadness, and intensity of those losses, and only recently have I begun to breathe them back out again. 

The reason I mention all of this is that I’ve been struck recently by how many entrepreneurs / startup founders spend 10, 20, even 30 years in that same kind of place emotionally. 

Sometimes, listening to episodes of the Reboot Podcast (mentioned earlier) is like watching people unwind their 22 year old self (with all of its embedded beliefs) from being Wired For Struggle. 

I wonder, why not short circuit that process and teach young entrepreneurs about examining beliefs about their product, and about their inner life?

Some of this is a matter of altruism, and about acknowledging that we all suffer, but I think it’s more than that. It’s also about decision making, negotiation, and about building sustainable and profitable companies. We can’t negotiate properly or make good decisions if we aren't whole people, and we can’t be whole unless we understand our beliefs and our assumptions. 


…last week I mentioned how important frameworks are in the early stages of entrepreneurship. It’s something I believe in not just for companies, but also for individuals. Below is a checklist I use regularly to dig into my beliefs, which anyone is welcome to copy, trade, edit, or use however you see fit in part or whole. There are a few more in this doc as well. 


A checklist for testing beliefs (about your product or yourself)


  • Give yourself room to breathe, and to be uncomfortable — as Kyle Wild pointed out, take a break, go do something different. Sometimes that requires a trip to Burning Man, sometimes it doesn’t. The point of taking a break is not to step back and say that you’re amazing or awful, it’s to get a more honest picture of yourself, your work, your heart, and to give you room to appreciate what you are already doing and imagine what more you can and should do. You don't necessarily need to go somewhere totally different or do something radical in order to breathe and be uncomfortable. Sometime it’s as simple as a direct examination of your brain, heart, or beliefs in whatever environment you are already in.


  •  Identify what’s truly at stake — one of the things I’ve learned over the years in project management, product, and operations roles is that it’s ok to let off steam or spend time working out how you feel about something. But ultimately what you need to know is what happens next, and how you’ll incorporate what you've learned or negotiated in a given situation. It helps when you don’t get caught in the weeds on things that are less important long term but evoke a strong feeling. “What really matters here?” is the question that goes with this. 


  • Encourage yourself to be passionate, but remember that most of the things that matter exist outside of your head, in the world with people who are directly a part of your life— this is a tough one. Basically the question here is, am I really the only person affected / upset / passionate / confused about this idea / problem / place / thing? Usually the answer is no, and it’s important to remember that you can balance your own beliefs and emotions while also listening to and honoring those of other people. 


  • The most critical thing an entrepreneur can do in building both their business and self is create / maintain momentum in the right areas — this is really a hidden secret for entrepreneurs / startups. Rarely if ever do you know the answer or long term vision for your life or the life of your company. It’s more important to simply define the areas / themes that are important, and keep returning to them. Most of the time that’s where the useful answers come from, because in an ecosystem (and you and your company/product are certainly an ecosystem) things change constantly and what’s true now often isn’t in 3, 6, or 12 months.