February 24, 2023 Founders Note 005

005: Meditating Stressed Me Out

A few years ago a close friend asked me to go on a journey with him. He had signed up to be individually trained to meditate twice a day for 20 minutes, and he was looking for someone to join him. Meditation was something I’d done on occasion, but it wasn’t something I’d taken seriously, at least not as a practice. Meditation for me was like camping: something my ideal self does but my actual self doesn’t. 

This was also a period of life when I was training for ultramarathons, and I was deeply motivated by doing things that seemed too challenging to do. (See also: Being a startup founder.) So the decision to go from zero to a hundred (or 730, the number of meditations I would be committing to for the next year) seemed daunting – and therefore all the more alluring.

So I signed up to be a meditator. 

The initial training was all about how to meditate. You’ve probably heard the tips before: Try to not think, let the thoughts fade away, withhold judgment. In our private teachings, we looked at presentations about the physiological effects of meditating, as well as the metaphysical underpinnings of this particular type of meditation. But mostly we just practiced relaxing, closing our eyes, and being still for 20 minutes.    

This particular type of meditation was to be practiced twice a day. Not once, not three times. Exactly twice. The idea was that twice was more manageable than three times and more beneficial than once. Strict adherence was implied: Look, don’t even take another step in this training if you’re not going to commit to doing this twice daily. For all the self-compassion and mindfulness associated with the practice, the twice daily commitment was the one rigid non-negotiable. At the time, I thought it was a little excessive – what’s the harm in a little extra meditation one day and a little less the next? – but, like I said, I was in a period of life in which persevering through long commitments was really attractive to me. 

So I committed to meditate twice daily for exactly one year.      

Within a few weeks, I could effortlessly sit for the required meditation, a duration that seemed like an eternity until I actually sat for it. It didn’t feel like 30 seconds, but it certainly didn’t feel long and boring, what I’d imagined 20 minutes of doing nothing would feel like.

The actual meditating wasn’t the hard part; it was the scheduling of the meditation that drove me crazy. The morning meditation was relatively easy to remember to do – and actually do. It became the mental hygiene ritual of my mornings, and I generally felt much better afterward.

It was the required second meditation, due in the afternoon, that quickly became a problem. I either outright forgot about it or tried to cram it in between other commitments. Moments before leaving the house for dinner, I’d suddenly remember – and force my partner to “just wait 20 minutes” so I could sit in stillness. (As you can imagine, this request became something she really loved hearing a few times a week.) Or, panic stricken and laced with custom expletives, it would occur to me at midnight, after a really long day. Over the course of that year, I came to associate the second meditation with anxiety and stress. I came to dread it.

I committed to meditating twice a day for an entire year, and I kept that commitment, never missing a single meditation. But when day 366 arrived, I was done. After 730 consecutive twenty-minute meditations, I quit meditating because it stressed me out too much. 

It’s been two years since my year of meditation. At first, I thought I’d take a few days or a couple of weeks off as a way of resetting and ask myself, “Ok, now that you don’t have to meditate anymore, do you still want to?” Turns out, the answer was no. Life moved on, and I never returned to the habit. But recently, it’s been on my mind again.

My therapist Hal has known me for maybe 15 years. He’s seen me through nasty breakups, challenging business relationships, and the ongoing journey of self-discovery and acceptance. In the past two years, he’s also had a front row seat to Brian-as-founder. (Read: Brian stressed out.) In that capacity, Hal’s had one recurring piece of counsel for me: Meditate. Every time he says it, I think to myself, “I really should.” I think, “Why the hell am I not doing the one simple thing I know will help me?” And then I open another Zoom window and forget about it until my next therapy session.

My ideal self still thinks of myself as a meditator. I genuinely believe meditation is quite helpful. If you haven’t tried it, I seriously recommend it. But if you do, be good to yourself. Skip a time or two. Go all out and meditate for 30 minutes! Or, take a few deep breaths and call it after five. Whatever works for you.

On my end, I find myself thinking about it more and more, but I still haven’t meditated. (Hal rolls his eyes. Actually, he wouldn’t; he’d just kindly suggest I give it a try, as if he hadn’t told me to a dozen times already.) Maybe today is the day. Let me see if I can find 20 minutes to squeeze it in this afternoon.
Brian McGrath Davis Co-Founder