Suffering alone isn't a strategy

"I had the tough conversations. Reduced burn by half. Increased runway and surprisingly, velocity." John¹, a CTO at a well-known startup, told me over Zoom, the background betraying a home office shared with an infant. "I now work differently and more cleanly with the remaining team."

John wasn't new to coaching, and he'd tried therapy before, but with mixed results that made him hesitate. At the urging of his CEO, he tried a group experience facilitated by a coach that gave him a laboratory in which he could not just see his patterns of conflict avoidance, but work through them with support, and emerge with clarity and a new lens on relationships. He's continued to work with that coach since, building on what he'd started.

John was one of over 50 YC founders I spoke with about coaching. In the previous post, I covered the skepticism. Here, we'll meet founders who, like John, had to cross a gap first - between skepticism and a kind of value we can't see until we're on the other side.

Perception gap

"You can't connect the dots looking forward; you can only connect them looking backwards" – Steve Jobs

By our nature, ambitious founders strive for speed. Combine that with resourcefulness and top notch problem solving, which has gotten us this far for damn good reason, and we tend to look for those solutions "out there." Raising money, hiring the right person, designing the product, thought leadering on LinkedIn. Lastly, add a high tolerance for staring into the abyss and eating glass, and you've got the best startup machine that evolution could offer.

Not always a great setup for looking inward though.

For Tom, it was a deep reluctance to ask for help. Rooted in unexamined beliefs about manhood and weakness. After 3 years of trying to fix it himself through self-help books and meditation, he started experiencing nearly daily panic attacks. It took another 4 months before he accepted his wife's pleas that he get some support. The coach he worked with helped him unblock a lifetime of emotional constipation and rediscover his agency. His new relationship with life led to increased creativity, greater resilience, more degrees of freedom in how to respond. "Like a superpower," he said.

The resourcefulness that makes founders unstoppable can also be unexamined, limiting us to the options we already know. Talking to fellow founders, investors, mentors, advisors, consultants - all of whom may have limitations, bias or a stake in the outcome. We've also got books, YouTube, podcasts, and of course, humanity's entire knowledge base streamed in through our favorite chatbot at will.

As Leon observed, "90% of foundational coaching knowledge is now a commodity." I'd go further - 100% of it is. There are no secrets. But if that's the case, why isn't everyone just totally crushing it all the time?

For only $20 a month, we can all have a Paul Graham bot tell us that it's time to go have that talk with our cofounder. But as I've reluctantly learned myself and see now with my clients², knowing what to do doesn't address the conflict avoidance that's now compressed two years of resentment into total paralysis.

Achievement fuel

"Greatness is not intelligence. Greatness comes from character. And character isn’t formed out of smart people, it’s formed out of people who suffered." – Jensen Huang

One of the most common beliefs I came across is that pain is required for fueling motivation. As Rohan put it: "What drives me is the edge of needing to do better and achieve more. If I fully solved it, would the fire go out?" It's not the kind of question we can bring to a board meeting.

The drive for growth is undeniable. What's questionable is the fuel. Self-criticism and fear of inadequacy work, maybe even really well, but only for a time before burnout. The smog produced on the way touches everyone. But eventually, some of us discover there's a cleaner alternative.

"It made me realise that suffering wasn't a necessary part of success and that I could structure my work and life to be both joyful and productive," reflected Ali, a founder with a recent exit, on the value of learning to treat emotions as data instead of annoyances to control.

Jensen was prescribing more suffering to the poor Stanford students. I wish you more purpose so you can use suffering as a tool. Because adversity does build character. But there's a difference between adversity that grows us and the suffering we mistake for strategy. If the only thing driving us forward is fear of what happens if we stop, what's pulling us forward?

For Jessica, it was years of overwork and ignoring a health issue that took her to a breaking point, and finally asking for help. The shift was profound: "It’s like changing the lens through which you look at things." And from a more resourced place, she found herself more effective in the startup which soon saw revenue rise 50% after a long flat period. The surprising discovery: "You can build and be productive from a good place, not just chaotic and painful."

Sometimes the surprise came from discovering we're on the wrong path. Michael was promoted to engineering manager and his company hired a coach to help with the new burdens of leadership. Turned out, his strengths and passion weren't aligned to that, and the coach helped him make a successful transition back to being an individual contributor. "I thought I'd get better at leadership, communication, authenticity. And instead, came away with switching jobs."

Readiness, meet willingness

“The cave you fear to enter holds the treasure you seek" – Joseph Campbell

Evelyn was also promoted into leadership and the company sent her a coach. The discoveries from the 360 the coach ran made an immediate difference, with a colleague that said “whatever you’re doing with coaching, it’s working." When she started her own company, she knew she had to evolve even further and hired a coach herself. She saw how much she was holding herself back from being the leader she wanted to be: "My need to please people may not lead to best results for the company." Instead of seeking permission from others, Evelyn learned how to give permission to herself to show up with more confidence and assertiveness.

Albert built a successful fintech, but the company's performance slowed after their Series C. An investor introduced him to a coach, which felt like an extravagance to spend money on. "What would I get that’s different than talking to friends and mentors? Why should I pay for something I get for free elsewhere?" recalls Albert. He trusted the investor and decided to try it. What he discovered was the avoidance of the answer he already knew - letting go of an underperforming exec - because he was afraid of the ensuing mess. The coach helped him make peace with it and navigate the next steps "without the emotional rollercoaster."

There were many more stories, but where it all seemed to start was willingness - to ask for help, to learn, to be challenged, to feel one's emotions (those pesky things). To face what a part of them already knew. Says Gabe: "that's the only place I have to chat with someone to uncover what I really think I should do."

And when it works, the benefits compound. "It's someone that knows you so well and how you think," says Peter, adding that "90% of it was problem identification. Once it's understood, it's easier to change." Brett, whose coach supported him through cofounder breakup and fundraising, has kept up the weekly sessions for years and says there's "always something actionable after."

Is the juice worth the squeeze?

Maybe we're already running at 120%. Maybe our calendars are already a losing game of Tetris. What's certain is that coaching costs real money. The kind we'd have to justify to a cofounder or that voice in our head that tracks every dollar against runway. It also takes real time. Sessions, reflection, the kind of slowing down that feels almost irresponsible when everything's on fire. Inertia's a hell of a drug.

But as Peter asked himself before signing the check: "if this all goes to shit, what will I have to draw on?"

In the next post, we'll see how founders look at the return on investing in the most important asset in the company.

1. All names have been changed to protect privacy.
2. If you're hitting a ceiling in your leadership and would like to have a chat, shoot me a DM.