Lessons from 35: The life-changing impacts of extreme transparency, extended free time, and moving with conviction.
This past year has been one of the best years of my life, and I believe it will likely go down as one of the most pivotal years in my life arc.
My 2nd child Poppy was born, and my family has been lucky to remain healthy and Covid-free throughout the year. My wife and I have remained gainfully employed. With that foundation of health and financial security, coupled with all the extra time at home, it’s allowed me to spend a good amount of time contemplating big, important questions about what matters in life. And my views on relationships, work, and time have evolved quite a bit throughout this year.
This mindset shift has been a direct result of 3 primary lessons I’ve learned, and acted upon, in the past 12 months.
Without further ado, here are those 3 big lessons I learned in my 35th year:
Lesson 1: The positive effects of extreme transparency — how speaking your mind and not holding back builds trust.
One way that I learn is by watching successful people and seeing which traits of theirs seem the most attractive and tend to drive what I deem as their “success”. Whether this be in business, investing, or relationships in social circles, I watch how others act, I see how they interact, and I see how people respond to them. And I reflect on these experiences afterward and think about how I could potentially incorporate any of these traits/styles in my own life.
In doing so, one character trait that is a hallmark in people that I trust, and that I’ve grown to value more and more over time, is transparency. People who say what’s on their mind, not holding back or putting a nice “spin” on things unnecessarily. I know where these people stand and what they’re thinking, and I’m not left guessing what’s going on behind the scenes.
One of the first people I’ve realized and appreciated this trait in is my good friend Josh Britt. His social approval rating in our peer circles is unanimously positive. He’s a new-age renaissance man, worldly in food, wine, business, travel and he’s a sick amateur deejay. And he’s a really nice guy. But he’s also the guy who will call people (me) out on their (my) bullshit. Say something dumb, act inappropriately — immediate feedback. You might get 3–4 compliments in a row, and then a big dig. I find it to be hilariously effective. And I think the primary reason I like this style so much is that everyone always know where they stand with him — there’s no guessing.
I’ve experienced the opposite of this in the corporate world quite a bit. People who say what they think people want to hear, or “yes” men. But I never really know what these people are actually thinking or believing deep down. I’ve grown to distrust those people. Give me the “asshole” who speaks his mind, but speaks honestly, 10 times out of 10 over someone who says whatever they think you want to hear. In fact, I think one of the primary reasons assholes can be so attractive is due to their transparency and not holding back.
So I decided to start applying this in my life, in a fashion I’m calling “extreme transparency”. The goal is not to hide things in work or life relationships, and to speak what’s on my mind without holding back.
Applying this first in my job as a consultant in corporate America, I’ve started routinely disagreeing with my clients and/or bosses. I put forth my perspective, not really caring about how it will be received. When problems come up or things are behind, I don’t hide the situation or dance around it — I talk about it immediately and explain the reasoning. I purposely “wear my emotions on my sleeve” using facial expressions to show my agreement, disagreement, questioning, etc. (increasingly important on zoom video calls).
And in my experience executing this style over the past 6 months or so, this extreme transparency has been received incredibly well. It helps me build trust more rapidly because people believe what I’m saying, because I don’t hold back. I say what’s on my mind. And people respect that. Sometimes I’m wrong, and I admit it (a subtle sub-lesson here — admitting when you’re wrong is also a really valuable tool in building trust). The ultimate outcome of this is my opinion is sought after much more than it used to be, and I’ve become a much more trusted advisor.
This has worked well in my friend group relationships as well. In my social circle in 2021, we routinely talk about money, investments, ideas and feelings that were once taboo or off the table. But the world is changing rapidly and some social norms will need to change with it, and I don’t see the value in marking topics off limits within close friends just because it was off limits for older generations. If something’s on my mind I talk about it. And again, I’ve found that other people want to talk about these topics as well, and we take the taboo-ness off the table. This leads to deeper conversations (often over wine), which leads to deeper trust and deeper relationships. And deeper relationships with a core set of friends is one of my favorite outcomes of 2021.
What I’ve described here conceptually isn’t super revolutionary or even that “extreme”, but it is a good start on the path to transparency and increased trust building. As we move into an increasingly digital world, with less in-person interaction, I believe trust is going to become increasingly important as a true measure of social currency. I’ve certainly got a lot of work remaining in this area, but I’m excited about this start and to see the longer-term impacts of this strategy on business and social relationships.
Lesson 2: Extended free time can be life changing. Or how “lifestyle design” >>> the 9–5 life.
With the birth of my daughter Poppy in September, I was lucky enough to enjoy 7 full weeks off from work for paternity leave. In fact, this was my 2nd paternity leave in an 18-month period, with my son Archie born last July (god bless my wife!). Before my 2 paternity leaves, I hadn’t taken more than 1–2 weeks off at a time in my entire 12-year Corporate America career. And then in the stretch of 18 months, I had a combined 14–15 weeks off for leave.
And guess what — leaves of absence are freaking awesome! While the first few weeks with a newborn can be a blur, my wife and I quickly found a good routine. I got to wake up each day and make my own schedule, with no one telling me where to go or when to be there (other than Poppy). I worked out 5–6x per week. I had time to read, go on multiple long walks per day. I had time to think, and reflect. Time slowed down and days didn’t rush by.
“Sunday Scaries” were a thing of the past — Mondays are actually a great day when you aren’t staring down a 5-day work week. I didn’t have any “bus days” (a “bus day” is a phrase I coined from my early consulting years, best describing a day when I would’ve rather gotten hit by a bus on the way to work, then actually go through the work day).
The impacts of this freedom were overwhelmingly positive. My fitness levels went up. My happiness levels were up. I got to spend tons of quality time with my family, and we grew closer. Overall, I felt great and genuinely looked forward to each day.
This feeling of “time freedom” is addicting. I get why corporations don’t go handing out leaves — if everyone knew how great it was, no one would come back.
I’ve found myself over the years being jealous of my friends who own their own businesses. For younger Tyler, this jealousy was likely tied to the status of being a business owner, or the implied income. But I care a lot less about these factors as I grow older (while income of course is a baseline requirement). Now I’m jealous of them because of their ability to create their own lifestyles around their work. No one tells them where to be or when to wake up.
To be clear, this lesson and concept is not akin to retirement or not working at all — I’m equating it to lifestyle design. Being your own boss. Working when you want, playing when you want, relaxing when you want. I love the “work like a lion” mindset — work really hard for short stints to “get your kill”, then eat, reap the rewards and rest. Then repeat.
This is a fundamental shift from the 40-hr work week, Corporate America lifestyle. And thinking about making the jump is scary and comes with risk. And transparently I’m not there yet, but I do know it’s my ultimate goal.
My primary reason — after having experienced two extended stretches of free time and lifestyle design, I know how good it feels. And it’s really hard to go back. So my focus now is on how to unlock this lifestyle forever vs small stretches.
Which is a great segue to my final lesson from the year.
Lesson 3: The value in moving with conviction. Said another way, make big bets.
Historically I’ve been somewhat of a “micro-better” when it comes to gambling or investing. For years I was the guy betting $20-$50 on the game, while I watched my poker and DFS-playing friends making bets 10x-100x that amount on a routine basis. Even when I was lucky enough to go on real heaters, I’d win a few hundred bucks or maybe a thousand — but I never won big. While I watched others enjoy huge 5-figure and even 7-figure wins.
When it came to personal investing, it was the same story. I had a track record of smaller bet sizes (although growing a bit over the past few years), without ever taking on too much risk. I’d made a few good options plays, but lost on a few as well, and nothing major ever really came from it. All while watching others making huge windfalls and life-changing wins.
Ever heard the phrase “Play stupid games, win stupid prizes”? The same logic applies to low stake wagering in life. Play low stakes games, win low stakes prizes.
The tipping point for me came in December, as I started buying Bitcoin every Sunday with what I had earmarked for my NFL gambling money, a couple hundred bucks a week. As I was doing this “micro-investing”, I was also doing a lot of research on cryptocurrencies as an investment play, reading thought leaders’ opinions, and I had become more and more convinced that this was a really smart investment decision.
But at the same time I realized betting on bitcoin, or anything really, with small dollar amounts wasn’t going to get me anywhere. So what if it 10x’d? There would be minimal upside. That money would be gone in a single family vacation. I really believed this could be a life-changing bet and I knew for once I needed to bet bigger.
So I sat down with my wife, laid out my investment thesis, and we mutually agreed to invest 10% of our net worth into crypto. Finally, a big bet.
I acted almost immediately, and we built out our position across late December through early January — moving quickly and with conviction.
While I firmly believe this investment will pay off in spades, this lesson isn’t about touting a single investment decision or crypto, it’s about the concept of making up your mind, betting big on yourself and then acting on it.
If you want to change your life circumstances, you need to make calculated, big bets with asymmetric returns. Asymmetric here meaning bets that have capped downside (at most your initial investment) but huge, potentially unlimited upside. Stop micro-betting. Stop widespread diversification. And stop sitting on the sidelines.
I’m not saying to rush in. In fact, I typically do the opposite and delay, while doing my research and forming my opinion. But when you do decide to move in, once you’ve done your research and you’ve decided something is worthy of investment — bet big. Move with conviction. If you’re right, it can be life changing. If you’re wrong, lick your wounds, rebuild the coffers, and start researching for the next play.
On my death bed, I don’t think I’ll regret betting big on myself or something I believed in, and I don’t think you will either.
These lessons have greatly shaped my personal philosophy on life in the past year and have impacted several of my personal relationships for the better. Essentially my entire focus has shifted into applying lesson 3 (moving with conviction), so that I can unlock the potential of lifestyle design and more free time (lesson 2). And then taking and transparently sharing these ideas more openly with friends, colleagues or even people on the internet (social media and the coming metaverse) to build trust and deepen relationships (lesson 1).
I’m excited about these lessons. I’m excited about keeping an open mind in this rapidly changing world and maintaining an evolving outlook on life.
I can’t wait for 36, a post-pandemic world, and the roaring twenties to get underway.
Thanks for reading and thanks for all who contributed to my 35, directly or indirectly.