My first experience with therapy was in elementary school when I was unexpectedly put in a room with a school counselor who wanted to talk to me. I was in trouble; none of my friends had ever been sent to the counselor before.
When I got to her office, she introduced herself and asked me to take a seat.
It was the first time in my life I really sat down to talk to an adult stranger.
She wasn’t my teacher or classmate and she’d never met my family. All she knew was that I did something to earn me a seat in that chair at that moment.
We had work to do, and it had nothing to do with grades. It was about my behavior. It needed to change. Or else. I trusted her that she wanted to help.
I ended up seeing that counselor a few times. And she did help. I realized some things about what I was doing wrong. I realized I was a bully... sometimes to other kids but also to my teachers.
I had an authority problem. I felt the need to undermine them to feel important. If I could show them I was as smart as them — smarter than them sometimes — I would transcend our role gap and be an equal. I wanted to grow up and be taken seriously.
I was 10.
I grew up a lot through that period. I’d like to think it has made me more aware of others. My good grades (and expectedly improved behavior) ended up getting me to a good college, earning me a bachelors and masters degree.
The realization that teachers were just people doing their best and that adults were people who had simply been alive longer than myself was a massive turning point in my relationship with authority figures.
My relationship with authority still isn’t perfect, but it’s functional. It’s a work in progress.
Ten years later I was struggling. My relationships with my co-founders and girlfriend were falling apart. My startup was falling apart. My parents had divorced a couple years prior. We just put down my 14-year old childhood golden retriever. A year before that I left my high-paying Wall Street job. I held $40k in deferred student loans. I’d borrowed money from my mom (and was about to need to borrow from a friend). I needed help with my eye surgery financing payments and with buying a car to get around FL. I was paying $400/month to live in an old victorian house with 5 college guys. I had a masters degree and I was living with sophomores.
One of the developers working with me on my startup told me he was going through a tough breakup and was seeing a counselor on campus. It was helping him a lot. As it turned out, I had access to the University of Florida’s health and wellness services because my startup was headquartered in a college-funded startup incubator.
So I scheduled an appointment.
Once again, I was talking to a complete stranger about the most intimate things in my life. It was her job to listen and ask questions.
Our conversation had nothing to do with authority this time.
This time it was about money, ambition, and self-perception. It was about defining success, as an adult.
I was defining myself by my work and asking a whole awful lot of the world. I was trying to impose myself on the world in a way that felt unnatural. Founders need to be imposing. But when I imposed, I felt guilty.
My guilt went deeper. I convinced people to go into a journey with me into the unknown. It felt like I dragged them into it by being persuasive. There was a moral responsibility to selling, recruiting and fundraising that I never felt before. Good faith efforts mattered. People were depending on me.
Those sessions helped realize I was on someone else’s path. It was much better than investment banking, but it still felt wrong.
I was pushing myself, and the feeling was pure burnout. I had lost a lot of my mojo and wasn’t as confident about my abilities (or ability to maintain interest) as I was at the onset of the company’s life.
So I started kayaking in the middle of the day because, if I had to endure the suffering that came with being my own boss, then I was going to enjoy the perks too. One of those perks was kayaking on a random Wednesday afternoon without telling a single soul:
I ended up exiting the bad relationships and letting my ego take a back seat.
I found real humility for the first time since my days of fraternity pledging. I was back in a beginner’s mindset equipped with the indisputable evidence that I don’t know everything. Far from it, I had a LOT of learning to do.
I shut down the company and accepted a $52k salary with a Series B startup in SF under the customer support umbrella with the hopes of growing into another role as I proved myself. I felt a little overqualified but hey, I had no evidence that this was actually true; I was in no position to be picky.
Here we are 3 years later. I’m a product manager. I can express creativity and problem-solving without the all-consuming pressure of being a founder. I feel engaged and challenged with my work.
No burnout risk.
I’ve found mentorship and coaching to be very helpful in the past few years. The expertise some folks in the Bay Area have developed, and their willingness to share with younger people, is something I’m extremely grateful for. A select few have gone from trusted strangers to real mentors. Having practiced vulnerable openness in past therapy/counseling sessions has made my sessions a lot more useful with the folks who give me advice. We cut right to the important stuff.
Sometimes, the hardest part is knowing what I need help with.
For me it’s also a lot about getting out of my own way.
It would be silly for me to write this post without also acknowledging the helpful role of podcasts as an influence in my internal dialogue. Specifically, I’d like to give a big thank you to the folks at Reboot. Jerry Colonna and his team have been producing a phenomenal podcast. I’ve savored each episode. These sessions give me a lot of the benefit of going to therapy, for free. The reason is simple: when I expose myself to other people’s openness and vulnerability, it makes me more feel more open and vulnerable.
Check it out here: https://www.reboot.io/podcast
Seeing a counselor/therapist/coach has helped me get through some tough times. In a lot of ways, each of those periods were inflection points. Local minima on a long and winding journey. There were a lot of other things that brought me back up from those low points and there were a lot more low points I didn’t write about. But the message holds.
A lot of folks are going through a tough time right now. I can feel it. Especially in the bay area. But many are being very quiet about it, at least with me. If this encourages even one person to open up to a friend or go talk to a therapist/counselor (in tech — a coach), I’ll be happy.
I’m lucky to have an amazing wife, family and friends to talk about a lot of stuff. But it’s unfair to ask them to take the time and energy to deep dive with me into the mess in my head - at the time of my choice. It’s perilous. They might not like what they find. Plus, they have their own stuff to sort out.
You never have to worry about that with a trusted stranger behind closed door; they’re just doing their job.
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