Like most things in life, being an entrepreneur isn’t quite what it seems. From the outside, it’s all freedom and flexibility, hustle, and grind. We’re besieged by media narratives that put entrepreneurs on a pedestal, something to be admired and emulated. All that slick PR spin rarely reveals the tempest inside: that internal storm that rages daily, providing both wind for the entrepreneurial journey and the power to sink it all in one gust. 

Over my years as an entrepreneur, here are a few things that I’ve learned to help me navigate the journey.

Manage The Downsides

In 2018 I hit bottom, we’d launched our platform on Ethereum and the cryptocurrency was crashing as we’d just launched on a very ambitious trajectory. It was like having the candle burning on both ends. I was struggling with the pressure of finding a product market fit while having to lay off valuable team members and making sacrifices on the home front for my family. At that time I found it incredibly hard to talk about the challenges and poor condition I was in. As an entrepreneur I’m supposed to be a source of strength, so how could I? 

The most effective entrepreneurs are risk mitigators. We protect the upside and manage the downside risks of our business. But, for some reason we don’t do the same for ourselves. We need to protect the upside (our mental health) by managing the downside (the relentless pummeling of competing priorities and demands on our time). 

A few focus areas that I’ve found to be particularly troublesome: 

  • Taking too many meetings. One of the biggest downsides to being a founder is that there’s always going to be more to do than you have time for. This is what leads founders to overwork themselves, lurching from meeting to meeting without taking time to set clear time management priorities. I know I’m not perfect at this..but you need to make sure that meetings aren’t the only thing on your calendar. Build in time for blue sky thinking and focused work—ideally at a time in which you can isolate distractions, avoid interruptions, and get in the flow zone. 
  • Managing expectations. As an entrepreneur, everyone around you has expectations. Your investors want 
  • Pillar of strength. Often, leaders must be beacons of strength.  After all, it doesn’t do anyone good if you make your entire team panic, or if your mental state influences others negatively. Sometimes, we have to internalize stress and exude calm, collected control for the benefit of our teams.  all too often, taken to the extreme. It’s important to build in moments of vulnerability so that your team sees the humanity in your leadership. Be a pillar of strength not just by absorbing everything and internalizing! Show strength by verbalizing and sharing. A certain measure of transparency does wonders for loyalty and team cohesion.

Choose Your Idols Wisely

All too often, entrepreneurs look up to companies and founders that maybe we shouldn’t. We follow the lead of media coverage, fundraising amounts and conference keynotes. It’s another measure of importance: if other people care so much about this company/founder, then they must be worth emulating. 

This led us down a path of bro culture and “growth at all costs” business models. We were served up a narrow slice of imagery, as far as what it meant to be an entrepreneur. We had the ballooning valuations of the likes of WeWork, coupled with an intense culture that rewarded tomfoolery over business fundamentals. How could we not wonder what it would be like to be Adam Neumann, who was a paper billionaire and living that hyped-up entrepreneurial lifestyle? The media obliged and many entrepreneurs looked to that as the model to emulate. 

Instead, we should be choosing our idols wisely. Looking for positive role models, like Basecamp, which has bootstrapped their way to consistent growth, stellar reputation and long-term success. With a focus on productivity and product over fundraising and PR, Basecamp has built something special that’s worth our admiration. These companies may be less “sexy” and larger-than-life, but isn’t that the point? We’re here to build sustainable businesses for the long haul, not fundraise and flip.  

We need to ask ourselves:  Who do I want to be? What reputation do I want to have once this business is done and over? Which values are important to me and how am I living those values in my daily life as a founder?  And, perhaps most importantly, which part of founders’ personal experiences aren’t being told by the media and through the public persona? We’re all complex creatures; we must remind ourselves but nothing is as perfect and rosy as it seems from the outside.

Nurture Your Biggest Fans

Similar to the concept of the invincible entrepreneur, the concept of “hustle and grind” has done immeasurable harm. The coverage of entrepreneurs who the truth is that—those who can’t separate themselves from their businesses—will suffer from an identity crisis. It’s hard to see the forest for the trees when you’re staring at the bark all day.

Stepping away from your business is how you level up your business. It’s the work-life balance that gives you the perspective and mental space to push ahead, make new connections and discover creative pathways to build your business. 

That work-life balance requires not just a personal commitment; you also need to be accountable to those closest to you. Make sure that you invest the time to cultivate a support group of your biggest fans. This group will give you the perspective and space to maintain an identity that isn’t 100% wrapped up in your business. 

Stay Honest

Humans are innate storytellers—especially to ourselves. We tell ourselves stories that aren’t always accurate…and eventually begin to believe our own version of the “truth.” This manifests itself outwardly as being disconnected from reality: an arrogant, aloof and likely really unpleasant human. 

I find that there’s a lot of power in staying honest with yourself and relying on your biggest fans to guide you gently back onto the path as needed. It’s that honesty that gives you the space to find your calm within.