Lessons Learned in 2021

Kiva Dickinson
8 min readDec 31, 2021


2021 was a really good year. I got married (legally — thanks COVID; wedding is still next year for anyone keeping score); the business I started in 2019 really started hitting its stride; and the vaccine allowed me to make some amazing memories with friends and family who I had missed dearly.

2021 was also incredibly fatiguing. Postponing our wedding for the second time took a toll; the loneliness of solo entrepreneurship hit harder than it had in the past; the same commute from bedroom to home office started to make the days blend together; and the home workouts became more monotonous and less frequent. The result of these factors was a mentality that was far more fragile than I’d had in the past, which did not mesh well with a growing portfolio facing the challenges of iOS 14 and supply chain chaos.

Lately I have focused on unpacking the problems and fixing them to get my momentum right for 2022. I reset my personal fitness routine, I’ve gone back to my co-working space for a change of scenery and I made the exciting decision to expand the Selva Ventures team in 2022 (more on this soon). More importantly, I have embraced the notion that entrepreneurship is both a marathon and a sprint, and that it takes a mentality of balance and intensity. This realization has pushed my curiosity in how to build the right mental strength to fight through the bumps, come out stronger and enjoy the journey. The latter might be the hardest for me, but this journey really only is worth it if you enjoy it while it’s happening, not only at the finish line.

Last year my book selection was largely autobiographical: how have icons like Stephen Schwarzman and Barack Obama managed the weight of their decisions and responsibilities? This year my curiosity was a bit more theoretical: what are the ideas that drive the optimal mindset to achieve success and happiness? After all, they should be quite correlated if done right.

That curiosity brought me to an interesting set of books and passages exploring psychology and emotion from a diverse set of authors: an investor, a computer animator, a Holocaust survivor, a philosopher and a Hollywood actor. There is an incredibly powerful thread of positivity in their messages but an equally heavy respect for the difficulty in achieving that mindset. What I find most uplifting is the choice of mentality will always be ours, no matter what happens around us or to us. I’ll be carrying that with me next year and beyond.

1. If your products are decisions then exercise your mind

Rockefeller’s job wasn’t to drill wells, load trains, or move barrels. It was to think and make good decisions. Rockefeller’s product — his deliverable — wasn’t what he did with his hands, or even his words. It was what he figured out inside his head. So that’s where he spent most of his time and energy. Despite sitting quietly most of the day in what might have looked like free time or leisure hours to most people, he was constantly working in his mind, thinking problems through.
— Morgan Housel, The Psychology of Money

LeBron James famously spends $1,500,000 personally per year on his body to improve his recovery and longevity. When I’ve discussed that number with friends and colleagues, it’s often treated more like a fun fact than an applicable lesson. The analogous asset to LeBron’s body for anybody in business, law, academics or medicine is their mind; if your output isn’t the things you make with your hands then it’s the decisions you make in your head. John Rockefeller had this right over a hundred years ago.

Why is it then that we are so stingy and passive when it comes to investing in our mental fitness? If our goal is to make decisions at the highest level, then should we not be viewing meditation as our weight room, sleep as our recovery process, therapy and coaching as our personal training? Should we not be blocking time to read as an investment in idea generation? My resolution in 2022 is to be much more intentional about my mental fitness; fewer to-do lists with the illusion of productivity and more performance when it counts.

2. Mistakes are not “necessary evils” nor evils at all

All the time in my work, I see people resist and reject failure and try mightily to avoid it, because regardless of what we say, mistakes feel embarrassing. There is a visceral reaction to failure: It hurts. We need to think about failure differently. I’m not the first to say that failure, when approached properly, can be an opportunity for growth. But the way most people interpret this assertion is that mistakes are a necessary evil. Mistakes aren’t a necessary evil. They aren’t evil at all. They are an inevitable consequence of doing something new (and, as such, should be seen as valuable; without them, we’d have no originality).
Ed Catmull, Creativity, Inc.

I have heard since I was in grade school that mistakes happen and what matters is how you learn from them. This is nothing new. What IS new for me this year is the realization that my mental model around mistakes was always retroactive. In other words: “now that I have made a mistake and I cannot undo it, what can I learn?” What’s wrong with this mindset is that it does not calibrate my emotions to expect that mistakes will happen, so it does not prepare me to be steady when they do.

Ed Catmull is the co-founder of Pixar. Like his insight above, my approach to mistakes should be proactive; they should be the byproduct of big ambition and relentless execution that is often outside my comfort zone. They are no more evil than the early cuts of Pixar films that never reached our screen (or even the very few flops that did). I need to be better at this — I have a model on my laptop that shows how my returns work with some investments failing, and yet I often struggle to manage the stress of turbulence at it’s happening. I need to remember that these unique bumps in the road are what can make our process uniquely successful going forward.

3. Our greatest power is our choice of mentality

If I had to name my therapy I’d probably call it Choice Therapy, as freedom is about CHOICE — about choosing compassion, humor, optimism, intuition, curiosity, and self-expression. And to be free is to live in the present. If we are stuck in the past, saying, “If only I had gone there instead of here . . .” or “If only I had married someone else . . . ,” we are living in a prison of our own making. Likewise if we spend our time in the future, saying, “I won’t be happy until I graduate . . .” or “I won’t be happy until I find the right person.” The only place where we can exercise our freedom of choice is in the present.
Dr. Edith Eger, The Choice: Embrace the Possible

Edith Eger’s book might be the most inspiring thing I have ever read. Eger was born in 1927 to Hungarian Jewish parents and by age 16 was held at a concentration camp in Auschwitz; while she suffered the tragedy of her parents’ and boyfriend’s death, she survived with her sister and still lives in the United States today. I could not possibly do her story justice, this is one you just need to read — you will not regret it.

Edith is a psychologist now, and has dedicated her life to helping people work through problems of their own with such a powerful philosophy. Her north start is the control we have in the present: to overcome whatever adversity may be around us, past or future, and choose to be positive. Maybe this seems easier said than done, but Edith has been through the darkest acts of humanity to emerge as a beacon of hope and positivity. I can’t think of a more credible leader to look up to in search for the right mentality.

4. Strike while the iron is cold

It is a pity, therefore, that the insights on offer in the consulting room are so negligible in the wider culture. Their conversations feel like a small laboratory of maturity in a world besotted by the idea of love as an instinct and a feeling beyond examination. That Mrs. Fairbairn’s room is tucked up some tenement stairs seems symbolic of the marginalized nature of her occupation. She is the champion of a truth that Rabih and Kirsten are now intimate with, but which they know is woefully prone to get lost in the surrounding noise: that love is a skill, not just an enthusiasm.
Alain de Botton, The Course of Love

I usually don’t choose fiction for these annual reflections but this book and passage stuck with me. It has always been my greatest ambition to be a good husband and father; getting married this year has made that more real than ever. The lesson I’ve learned is that wanting to be great is not enough — like anything worth doing it takes hard work and sacrifice, and usually can’t be achieved without help.

The passage from the novel above refers to a couple’s therapist (a profession that I expect to see a TON of growth in the 2020s) and her positive impact on the relationship of the main characters. This person stands for all of the unsexy but necessary parts of building a lifelong partnership — where skill is built on truth, empathy and understanding. To achieve such a lofty ambition couples need to start building skill and strength long before there is an existential problem that needs urgent attention. As my friend’s therapist says, we need to “strike while the iron is cold”.

5. Thank yesterday’s setbacks for today’s blessings

The problems we face today eventually turn into blessings in the rearview mirror of life. In time, yesterday’s red light leads us to a green light. All destruction eventually leads to construction, all death eventually leads to birth, all pain eventually leads to pleasure. In this life or the next, what goes down will come up. It’s a matter of how we see the challenge in front of us and how we engage with it. Persist, pivot, or concede. It’s up to us, our choice every time.
— Matthew McConaughey, Greenlights

Mistakes are not “evils” and neither are setbacks. Life is filled with setbacks that knock us to the ground, punch us in the gut and threaten our feeling of hope. The thing is, in my life I’ve felt these setbacks most often when I’m striving for something that is worth striving for. I also can’t think of a great thing that has happened to me that wasn’t a very clear output of a difficult setback. Matthew’s would say you can’t hit green lights without passing a red light.

Recently I shared a reflection on a setback I had five years ago. It sounds silly to feel this way in hindsight (rejections just aren’t that big a deal in the grand scheme of things) but for years I was embarrassed to speak openly about what this did to me. It’s been a mindset shift to view this event in my life not just as something “I can’t change so shouldn’t worry about” but rather as a blessing that unlocked many of things I’m most grateful for today. It has also shaped my proactive approach to new setbacks: when I’m tempted by dejection or self-pity I try to think about what big win today’s losses will lead to. That’s a powerful mentality — as Matthew would say: “Alright, alright, alright”.

Happy new year. I hope 2022 is a great one for you!



Kiva Dickinson

Consumer Investor / Founder of Selva Ventures / Proud Canadian Living in San Francisco