Legibility
Brook’s birthday present to me is the perfect reflection of how I want to be seen.
I’m disappointed that I missed publishing any blog posts in 2024, especially as I get a lot of positive feedback from my friends. In short, 2024 was a pretty hectic year:
I navigated ‘exploration’, going from health tech ideation (Jan-Apr) to fractional projects in tech/growth along with corporate real estate + trucking (May-Aug), before taking a full-time role in October
I had ACL surgery (Apr) and plenty of ups and downs with the recovery process
I settled into Guelph, ON and bought + renovated a house with my partner (Aug-Oct)
While I originally started this post in July 2024, it surprised me how the title of ‘legibility’ continued to be relevant, even though I feel like I have a lot more figured out now VS several months ago. So, I decided to create this post to share some of my thoughts on the topic, how it’s evolved for me over the years, and what I’m still unsure about.
For anyone skimming, the tl;dr below:
Success quickly becomes relative after graduation, and is more a reflection of the lifestyle you want and what you are comfortable trading off
Structured optionality is infinitely better than endless optionality. I use the framework of open exploration, doing a deep dive, making bets, and then doubling down to land on something I’m happy with.
My relationship has challenged my worldview, how I view work, and what my previous self’s goals looked like
Being ‘legible’ (being understandable, your choices / life make sense) to your friends is challenging, but it’s more challenging to be legible to yourself. My values and environment change but my worldview carries a lot of debt from my ‘past selves’.
Choices like ‘take a less stressful job’ can feel more or less legible to your circle based on their worldviews and how they interpret your rationale / situation
While my current self is constantly changing, I aim to still experiment and hold high integrity in my choices for 2025
The older you get, the less you know
I believe there’s a fallacy amongst young people (i.e. students) that professionals have it ‘figured out’. They believe that we’ve picked our path intentionally and made calculated decisions along the way, both in terms of our careers and all the life events (i.e. marriage, kids, etc.) that we’ve taken on. In contrast, the college students I talk to seem to take the perspective of “I think I’ll like XYZ job but I don’t know beyond that”.
I surround myself with a lot of analytical folks; think the type of people who have spreadsheets to do their 2024 Year in Review, set micro and macro goals, and have check-ins throughout the year to stay accountable. One of my best friends made an extensive list to compare renting a condo unit (within the same city), while I myself got quite granular when trying to decide what to double down on in 2024 for work. On the surface, this perception of ‘highly calculated decisions’ makes sense.
However, I believe the opposite is true: once you leave the cushion of academia, your trajectory and decisions become quite diverse, and you don’t have it ‘figured out’. In school, you can narrow in on a career choice, pick that job (and prep for interviews, do internships, etc.), and embark on your career. Sure, there are some other decisions like the location you pick for work, but generally the sliding scale is (relatively) quite narrow re: the pay you’ll receive, what value you bring to the organization, etc.
As I went from my 2nd, to 3rd, to 4th job, and from 22 to my late 20s, some of my motivators in college no longer rang true:
Salaries are relative — Most jobs (within my field) feel attainable. Entrepreneurship is higher risk but with much higher reward. Even within entrepreneurship, there’s a sliding scale of risk/reward, if you compare starting a marketing agency (predictable, linear) to starting a venture-backed startups (binary success or failure, exponential).
Lifestyle is a choice — In college, it felt like ‘career’ was a constant competition of who worked the hardest / smartest to get the best outcome (a good job). Now, I feel like there are many more variables to this. Some are more extreme than others:
Extreme — Decide to get married and have kids earlier, which likely requires more sacrifice with work
Less Extreme — Dislike cooking and allocate a greater portion of your budget to eating out or getting meals delivered.
Success is relative — I’m privileged to be in a close friend group where everyone is successful in their respective careers. There are sliding scales to that success (i.e. $$ earned), but this is connected to lifestyle choices:
Being single usually enables you to travel more and focus more on work
Picking certain lifestyles (i.e. enjoying luxury clothes) will necessitate a higher income than someone who doesn’t need that
I’m entering an era where the next 10 years of my life feel like the purest form of ‘choose your own adventure’, where many of the inputs (money, work, etc.) are flexible and the challenge is making tradeoffs that allow me to accomplish the outputs (more money, relationship, family, health) that I want.
(Unlike some of my friends, I have some constraints (mortgage, fiancé) so that it’s not purely free play, but even those don’t limit the majority of choices with the right planning.)
Who do I want to be?
I’m a strong believer that endless optionality is a curse, and should be replaced with structured optionality. Over the past year, as I tried to figure out the question of ‘who do I want to be’, my framework looked like this:
Open Exploration — Make time to think, talk to lots of people, write about what I’m learning. See what interests me.
Deep Dive — Repeat the above but within a specific vertical / problem space. Start to carve out potential challenges that I could solve.
Make Bets — Start fractional (part-time, short-term) work with clear expectations of what I want to learn / accomplish. Most recently, this was two engagements, one for redesigning Go-To-Market for a legacy software company and another for launching a series of truck parking lots (corporate real estate) across the US.
Double-Down — Compare fractional work to goals and pick the option that is the best fit. If neither work, then restart the process with new information.
While my most recent rep (May to October 2024) worked for this, my previous rep (November 2023 to April 2024) did not. I initially started with open exploration, decided I wanted to make social impact, took on a few fractional projects (see WhileBeing, Potential) including an impromptu trip to Germany where I stayed with a friend of a friend (Welf, below) to see if we’d be a good fit as co-founders. At the end of everything, I decided that the focus area wasn’t a good fit for me and I needed to keep looking.
Welf made some awesome dinners in Germany and was very hospitable to let me crash with him!
It’s worth noting, perhaps a bit obvious, that “who do you want to be” doesn’t mean “what do you want to work on”. I did not think nearly enough about this, but there were some realizations that went beyond career.
Relationship
Dating has some parallels to the process above, although the ‘fractional’ component is more similar to going deeper with 1 person and seeing whether it has the legs for a long-term relationship (opposed to dating multiple people at the same time!). Follow-ons might include moving in together, buying a home, getting married, etc.
I was very fortunate to find my life partner in Brook, who I’ve been dating for 3.5 years and recently got engaged to. Similar to the above, we started on dates, committed, did long-distance, moved in together (Guelph), bought a house, etc.
But these are all ‘facts’, not aspirations. Relationships are a lot harder to characterize than work; it’s more synonymous with the lifestyle I want to live and the experiences I want to share with another person. As with personal development, my relationship also challenged a lot of my career worldview, with perspectives like:
“You work hard to create freedom. Having the optionality to work when you want and how you want is a very privileged position. It shouldn’t necessarily be filled with more work and making more money.”
- A bastardization of what I think Brook said, 2024
Without adding any other variables, the items of ‘work’ and ‘relationship’ already start to muddy the waters of who I aspire to be. For those familiar with No Bad Parts, there’s a fight between my Manager part who has career goals and wants to accomplish them with no blockers, and my Relationship part (both platonic + romantic) who wants to build on the support system I’ve created and acknowledges the tradeoffs that might come with pursuing that goal.
What I admire, even envy, about billionaire tech CEOs as much as I do Taylor Swift is that they have a relentless drive to accomplish a specific goal (‘being the best’) and likely acknowledge that other desires may take a back seat to that. While I use the word ‘envy’, as it would allow me to accomplish my maximum career potential, I realized that I don’t desire to be that type of person, and that I want a feeling of balance while continuing to excel in my career.
I don’t know exactly what that balance looks like, and there are a lot of unknowns I’m trying to solve… Both via my support system + network (i.e. mentors) but also through introspective, journalling, and leveraging structured optionality. Even with maintaining this balance, I strive to accomplish a lot in my career and have confidence that I’ll do great things. This is not a zero sum game in the most obvious sense; wanting to be a great father doesn’t mean sacrificing your career, and there are plenty of examples that prove that.
Who do others want me to be?
I mentioned earlier that students often have a skewed portrait of what the lives of their mentors and idols are like. As you can tell from the above, even I have a skewed version of myself and what my life should be like — my life has changed a lot over the past couple of years, as have my values, but my worldview has been slower to adapt and thus some of my goals may be based on lagging versions of myself.
That’s a lot to reflect on… Now, enter everyone else. My friends, my family, my LinkedIn connections. Some of these matter a lot less than others, but remember that everyone holds an image of who ‘Trevor’ is. Most people understand themselves through the lens of others, and try to associate with people who are like them to validate the decisions and perspectives they have. I’ve drifted apart from people who didn’t see the world the same way that I did, or had conflicting values. Even people who are quite similar to me in both these regards might be at a different chapter in life, and therefore talking to me would invalidate how they’re feeling (and vice-versa). I.e. someone who desires travel and anticipates having kids in 10 years would clash with my suburban lifestyle.
Check out the dryer I installed in my basement!!!! Talk about home ownership, am I right?
From a more macro perspective, we’re seeing firsthand that an ‘othering’ of worldviews is causing a polarization in the US (Trump) and is popping up across the world. It’s often portrayed as frustration (“I’m unhappy with the current administration because I’m not doing as well as I think I should be”) but I believe a lack of social understanding plays a major part (“Why are my tax dollars going towards people I don’t believe in / don’t think they deserve it”). It’s easier to look externally than internally when conflict arises.
While I digress on the political commentary, this concept holds a lot of weight with my close friend group and past versions of myself. How do I explain my decisions when my evaluation criteria is different than someone else’s? How much more complicated does this get when my criteria is changing and I’m still figuring out how to evaluate possible decisions against it?
As with previous examples in this post, some of these tradeoffs can be more obvious than others, so I’ll play out a couple of scenarios to show the contrast with the common mentality of being ‘career oriented’. The bolded item is the decision, and each bullet is rationale or a situation that could be more/less legible based on the mentality of a career-oriented person.
“Taking a less stressful job”
More Legible — Recently had a child or health scare, looking to dial it back.
Less Legible — Mental health suffered in their past role, need to reset.
Illegible — Looking to prioritize personal hobbies over work.
“Moving to a suburb”
More Legible — Bought a house with your partner and planning for kids
Less Legible — Capitalizing on market conditions to get a deal on a house.
Illegible — Wanting a slower pace than what the city might offer.
I have a laundry list of examples that span different areas, but I hope you get the idea. Keep in mind that the above presumes that the individual is open with their circle about their rationale. I can see many scenarios where someone’s mental health is suffering in their role but they play off their job switch as the chase for more money / status.
Even as an entrepreneur, there are levels of legibility and ‘understanding’ that I think most people have. One might start an agency to maximize cashflow and repeatability instead of starting a venture-backed company. But what if the same person decides to start a carpentry business because they miss working with their hands (less legible)? Or chooses to slow their agency growth to maintain work-life balance (illegible)?
We see entrepreneurs as “do it at all costs” people, and the influencers in the space continue to perpetuate that. Don’t get me wrong; you have to hustle as a founder and I’ve had many sleepless nights to create what I have. But the ‘do it at all costs’ mentality is oversimplified, and it needs to be so that everyone (including other entrepreneurs) can see it as legible.
Conclusion
I wrote this post because I still struggle to explain the decisions I’ve made - both personally and professionally - to my friends and to past versions of myself. A lot of the internal conflict I face is due to the latter, where past versions of my wanted something, see it as being more attainable now than before, but get frustrated when I choose not to pursue it.
My hope for 2025 is that I can prioritize legibility as a purely personal endeavour. I need to be legible to myself, address dissonance with my past versions of self, and get fully aligned on why I’m doing what I’m doing. I want to retain qualities that have served me well in the past:
Experimentation — Being dialed in with goals and clear about what I want to get out of an experience. Add timelines and check-ins, and revisit this as it’s likely to change.
Integrity — Care about people in my close friend group and always try to pay it forward. Things that feel good / right don’t always have an immediate ROI but at the very least, helps me sleep well at night.
I hope this was helpful if you’re struggling to be ‘legible’ — stay tuned for (hopefully) more frequent posts about some of my current personal / professional journeys!