I have always been taught to think a certain way about both personal and career growth. While many view entrepreneurship as offering a new path (freedom of time, income ceilings, etc.), in many ways it parallels this traditional perspective. It’s about time for a change.
First, some context behind the writing of this post:
I pivoted my agency (Divisional) into a marketplace last August and have spent the past year iterating and finding the right model that scales. Overall, I’m happier with the work and impact that we’re making.
Despite improvements, I’m overall no longer excited about this space and problem. For my fellow founders, this is a major revelation as there is no more ‘pivoting’ to figure out the model. Rather, there is a need to replace it with something new*.
The lack of excitement has led to an uphill battle; for the past several weeks, I have felt burnt out. I’ll take this in a separate post, but I think it’s important to note, as it likely frames how I view my path forward.
Unlike past experiences with burnout, I’m personally quite happy — I have a great friend group and a loving partner (with whom I have recently moved in with). This has challenged what I put value in, and forced me to look holistically at my situation and potential ‘next move’.
With that groundwork, I can share the structure of this post and its summary:
I have been conditioned from a young age to view personal / professional development in terms of milestones. To be in the top 1%, you need to be good at solving problems that are in front of you + planning for what’s next.
A lot of this perspective has adapted from how our parents’ generation operated; instead of ‘grind until you retire’, it becomes ‘grind in your 20s / 30s’, whereas other tenets like ‘build wealth to get freedom’ have remained the same.
To deflect from this, I can embrace what I call the Adventurist path. These individuals reject 5-year visions and believe you should never stop exploring. This entails revisiting your values, making space for introspection, and then starting to explore those areas of interest
In contrast, the other group (Masters) believe you should explore until you find the trifecta of being good at something, enjoying it, and having the market reward you for it.
As I’m entering my period of exploration, I don’t have an answer yet, but I have learned that modelling for efficiency is key to any business, and that only I can know my values (the ‘why’) to discern what problems are worth solving
Chasing Milestones
From an early age, I have been conditioned to optimize towards certain outcomes. In grade school (K-8), it was about being top of my class; getting the best grades, leading in extracurriculars, etc. But there was one inherent idea behind it all: mastery.
Yes, I tried to get the best grade on a 3rd grade Social Studies paper to please my parents and get recognition from my peers, but I wouldn’t claim that the pursuit of how the pioneers colonized Canada is inherently important to my future success. Instead, getting a good grade on a paper (and eventually, on the course as a whole), indicated to me that I was likely to be a high achiever. I would progress to do better on Grade 7 papers (also on pioneers, I think…?), evolve into Grade 10 history (still, something about Canadian history and pioneers…) and finally into a Grade 12 university credit on Globalization (finally, no pioneers!) that I could use towards my university applications.
Rinse and repeat; college is meant for learning and exploration, but I often found myself doing something to optimize for other things. Get good grades to open doors for grad school and recruiting, and towards the tail end of my degree, to minimize the work I needed to do (in class) so that I could pursue other ventures (starting an agency with a good friend).
The older I got, the less academic the pursuits became, but the core thought was still there. Get good internships to craft a good narrative, enabling me to get recruited by better firms, and eventually use that signal to start my own company. Even company building is a means to an ends; I build to scale and eventually have an exit (acquisition, sustainable cash flow, etc.).
The traditional perspective
This is what I’ll refer to as the ‘traditional perspective’. And the older I got, the more I started to question some of the tenets that this perspective embraced:
Grind in your 20s to enjoy life later
Work hard in your 20s so that you can have greater opportunity in your 30s and have to work less hard later in life. The enlightened perspectives here will argue that this time is spent on things that complement work, i.e. starting a family.
I’m very excited for the family planning stage of my life, but this seems a bit counterintuitive. Work hard so that you can continue to work (in raising your kids) so that they will have a good life and you can relax in your… 60s? In a sense, work to master your domain so that your outcomes will mean you no longer have to invest (work) as aggressively later in life.
I’m also in a very privileged position, as I know many of my 1st / 2nd generation friends are. Our parents had a ‘survival’ mindset; immigrate with $0, make a living for you and your family, and sacrifice — so that they don’t have to. Fast forward, I was able to take a lot of risks (with my parents as a safety net) and now have the freedom they wanted me to have. But I’m foregoing that freedom to enable my kids to have that freedom…?
Build wealth to give yourself freedom
Money is the greatest key to having freedom, as it removes a lot of the constraints that will prevent you from accomplishing your dreams. Working hard and building wealth - where a core feature is its ability to compound with investments, interest, etc. - so you aren’t prohibited in your future pursuits.
I’m a capitalist and a (fiscal) conservative. I love making money, and can attest that having money allows me to make better decisions with my business, personal life, etc. I’ll pay more for a gym membership so I can exercise when I want without waiting. I’ll hire more people so my company can grow faster and accomplish more.
I’m also limited by capital, either in reality or mentally. The reality parts are quite clear; I can’t buy the nicest house on the block, take the best vacations, or do anything I want without having to worry about working (making money). The mental parts are more subtle; I don’t buy the more expensive flight that leaves later because I don’t think it’s worth it (based on how much money I have), even though I can. I do grocery runs myself because I think it’s a rip-off to pay for (and tip) an Instacart person, when the time savings are excessive when compared to my hourly rate.
When do I really accomplish freedom? There will always be a bigger house, a nicer meal, etc. I can set benchmarks and have a rough idea of what gets me 80/20 freedom with financial choice, but that marker moves when I have kids (college funds, extracurriculars, vacations, etc.) or have evolving needs (cottage, home gym, etc.). Wealth gives me freedom, but pursuing it to have optionality for future freedom feels a bit like saving for a house that doesn’t have a price on it.
As you can tell, a bit of critical thinking left me with lots of questions. So, I reached out to my mentors, friends, etc. to get some answers.
Some of them were very practical:
“You can’t plan your next step without a goal. What do you want, specifically, in 2-3 years? How much money do you need?”
Others were very theoretical:
“Find what you’re most interested in and do that. Optimize for happiness and check the other boxes (i.e. money) when you need to”
The former led to spreadsheets, akin to this post, and the latter led to reading books like The Pathless Path and posts like Quit Your Job.
What does the non-traditional path look like?
The adventure approach
Those who reject the traditional perspective have some fairly hot takes:
You shouldn’t have 5-year plans or visions
You shouldn’t try to have 1 thing (i.e. job) check all your boxes
You should never stop exploring and asking questions
I call this the Adventure Approach. In this perspective, you are permanently ‘exploring’ and constantly trying to do things that energize you and reflect your interests. Contrary to what you might think, it doesn’t mean living the 4-Hour Work Week, adopting the F.I.R.E. movement, and travelling the world**. Really, it just means that you reject the idea of mastery.
Someone adhering to the Adventure Approach might do the following:
Work in sales at Procter & Gamble; their goal is not to be the #1 rep but instead to hit their quota and abide by their work-life boundaries.
Spend a couple hours every day in an art studio, learning to get better at a specific style of painting and trying new things.
Realizes they love painting and wants to do more of it — this requires moving to New York to be more engrossed in the art scene.
Quits their job (and cuts back spending) to make this move, taking a lower paying (but more flexible) sales job at a smaller CPG company
Gets a ton of validation from creating art but realizes that people can’t discover art the same way that they discover music, leading to difficulties in distribution / recognition
Builds a platform for art distribution, quitting their sales job to go all-in, and raises $3M to make it happen
Through talking to more artists, realizes that the income inequality in New York is the biggest barrier, and that’s caused by a lack of political awareness & flexibility
Steps down from the startup and joins a political activist group
As you read through that, you might have been expecting that this person has no interest in money and traditional success, when in fact, they accomplished what a lot of people would have loved to do (raising money and building a hot new startup). The difference is that it wasn’t a linear path from being a blue chip sales rep to being an entrepreneur; it was a journey that involved following their interests and giving 100% to the activities they chose.
This group believes that mastery is actually detrimental to following your value system. Think of someone who is in the top 1% of their craft, and needs to constantly train and upskill to move up (or stay in) the top 1%. Even if they lose interest in that craft or find better alignment in another area, they aren’t able to pursue it. I.e. it is rare to see a doctor, who endured several years of medical schools (including getting in), residency, specialization, etc. leave to pursue their passion of running a bakery.
It’s fair to say that this perspective is a bit extreme, but some of the greatest inventions & companies we know were built from radically new approaches. One could also say it’s a build-up of several generations; if you were the first person in 250 years to be able to ignore the pursuit of wealth, would you?
Exploring
When I started reading The Pathless Path and sharing my findings with friends & mentors, not everyone was enthused. Funny enough, the author (Paul) actually warns about this; but since several of the folks I talked to had actually read the book (or were at least familiar with the concept), I could give more weight to their opinion.
To my surprise, they actually thought the adventure approach had a lot of merit. You see, these people aren’t in favour of the traditional approach either. Mindlessly plugging away at a career on a set path is not fulfillment, even if you can become quite good at it. This group recognizes that when (if) you decide your current path is not the right one, you need to explore.
This means being introspective and actively asking questions about your path. Determine why you have fallen out of love with it, and what factors have influenced that shift. The rough framework for exploring is as follows:
Revisit your values — Understand what motivates and drives you. What do you look for in work and in your daily life? Has that changed?
Make space — The easiest option is ‘quit your job’ but that often isn’t possible (or necessary). Instead, it may involve clearing evenings or dropping activities that you are not strongly tied to (i.e. not your day job / income) and leaving space to introspect.
Start exploring — Have conversations with people who are doing things you find interesting. Begin to pursue some of the activities that you have had on your backlog.
So what is the purpose of exploring? This is where the adventure approach and mastery approach diverge, and how the latter begins to resemble how one might traditionally view personal & career growth.
The mastery approach
Adventurists (as I’ll refer to them from here on out) will argue that exploration is not a phase but a persistent state. You pursue what you find interesting and dive into those interests, uninhibited by a longer term goal or track that would prevent you from making changes. Make money when you need to, spend time on what matters the most to you, and avoid delayed gratification.
As we saw earlier with the P&G sales rep, it can lead to big changes that will have a significant effort (positive or negative) on your life***. However, it doesn’t mean that you necessarily devalue traditionally important things (i.e. wealth), so long as it aligns with your value system and interests.
Advocates of the mastery approach, or Masters, view exploration as a temporary stage. You explore to get re-rooted in something that you have conviction in, and thus are able to commit 100% to. While exploration for Adventurists is rather open-ended, for Masters, the goal is to discover something that fits the trifecta:
You are good at it — think top 1% or the ability to get there
You enjoy it — it gives you energy and you can spend lots of time on it
The market rewards you — it is well-paying and/or there is significant demand for it
This perspective more closely resembles the “do what you love” approach to life, where work-life balance is overshadowed by work-life integration, since trying to compartmentalize something you want to relentlessly pursue will lead to a suboptimal outcome.
Most importantly, Masters believe that while a specific project (job, startup, etc.) may not always align with your skills and values, there is always a project that will. By continuing to invest in that skill and take on projects and experiences that grow it, you are able to see gains from mastery. Each step is therefore tied to your past skills, and getting better at it opens new doors, and typically ‘better’ opportunities (lucrative, fame, etc.).
The hard pill to swallow with Masters is that to master something, you need to go all-in on the activity that you’re pursuing. You can’t get into the top 0.1% of something by doing it part-time or switching your focus every 6-12 months. It involves sacrifice and delayed gratification.
Does that mean Adventurists don’t work hard? No, in fact you could argue the contrary — if they’re incredibly passionate about a project and have higher value alignment than a Master, they may put more hours & effort in than them. They may see better outcomes. But their approach comes with a lot of risk and uncertainty.
While the minutia of decisions and how it’s interpreted may change, I found the basis of the two approaches to diverge on:
How they view exploration
How they view skill & personal development
It’s important to note that the outcomes of someone in each group can vary drastically. Masters aren’t necessarily obsessed with wealth building and fame, just as Adventurists are not hippies that pursue their own interests without limitations and live off the land. One trend I’ve found is that Adventurists are primed for adventure (hence the name) - they get bored doing the same thing and feel energized by tackling new things - while Masters are primed for mastery (again, in the name) - they want to get the best at something and get energy by continuing to invest in it.
(As a side note, I think it’s interesting that there can be diversity within a specific group but the core tenets / beliefs must be aligned. Some parallels to religion, i.e. Christianity and the Holy Trinity belief but practices & interpretations change by sect, perhaps…?)
So what does that mean for me?
You might be able to tell from this post that I have had something of a significant mindset shift, but my thoughts are not as clear as I - being a Type A planner - would like them to be. I know this chapter is coming to a close, but I don’t know what’s next. I’m actually not even in the full headspace of ‘exploring’, as I’m still committed to seeing my current chapter through.
I will share, however, some observations that I’ve had in the past 8 weeks of contemplating my options:
Model for efficiency, even when you don’t have to
In my last full-time role at Shiftsmart, I told my boss (Rob) at the time that I appreciate him teaching me about ‘operations’. The company was a SaaS solution paired with a marketplace that enabled the sourcing, screening, training, placement, and completion of blue collar work to be done efficiency (think mystery shopping, checklist inspections, call centers, etc.). After a gruelling 4 months with lots of spreadsheets, blank stares when asked for numbers, and late nights that I brought upon myself, I told him that operationally heavy companies weren’t for me, but that I had learned a lot.
What I had potentially learned, I had not applied. The next 2.5 years of business ownership was a rollercoaster of being behind on financial modelling, over hiring (and firing too late), and generally running the opposite of an ‘operationally’ sound company. Of course, I’m being harsh; but it wasn’t until I told myself “I don’t want to be doing this anymore”, did I start to take a serious look at how efficient my company was and find big improvements.
I think anyone could ask themselves the same question as a forcing function: What if you only had 20 hours / wk to do the job you have now? How would you build efficiency into your job, set boundaries, and ensure you have time for your other commitments? I think a lot of people don’t recognize this, and thus fall on the opposite end of the spectrum — working long hours, sacrificing health / relationships, and trying to ‘grind’ through it.
For me, this phase included realizing that Virtual Assistants (VAs) overseas could do the bulk of my work with the right training and guardrails and that we didn’t need as much technology as we needed (read: spend less per month on software). I only came to this conclusion when I was forced to; and I’m seeing lots of entrepreneurs (especially the venture-backed ones) born in the ‘boom’ of the past few years learn this the hard way.
In the future, I aim to approach everything with a “how would I scale this” mindset, with a mentality that Rob taught me:
Do the work yourself
Find a way to do it faster (tech / automation)
Train someone else to do it
Find a way to monitor their work
Only I know my value system & goals
A recurring theme of ‘advice’ from my friends & mentors is that they’re working with incomplete information. While I often tell this to people I give advice to, I often miss taking it myself.
No one knows what’s going on in my head, what motivates me, and how I operate. Ask the smartest person what you should eat for breakfast tomorrow, and they’ll likely have a slew of follow-up questions (”do you have high blood pressure”, “are you a vegetarian”, etc.) to create a well-constructed opinion. But their suggestion of shashuka won’t factor in that you have a fear of eggs due to a chicken incident while visiting family in Arkansas, that you have an odd distrust of Middle Eastern cuisine due to a bad falafel you ate 3 nights before, or that you are fasting due to a medical procedure and the whole thing was a trick question to begin with!
The ‘hard’ questions are ones that you need self-awareness to answer, and while others can help you ask the right questions, only you will have the answer. I aim to get some of these answers by reflecting on my experience, talking to people I’m interested in, but most importantly by sitting with the thoughts and seeing how I feel. At the end of the day, there are no wrong answers, just decisions that take you along a long unwritten path.
If you are also exploring and have thoughts on this post, please message me! And hopefully it won’t be another year until this blog lives again…
*I am not planning to leave Divisional or shut it down. Instead, I’m aiming to operationalize it and downsize my involvement so that I can make space for other things (explore). This might mean a sale, bringing on a new partner, etc. Rest assured (to my clients & team), there will be no drastic decisions. As of October 2023, we’re profitable and it’s taking a lot less of my time than it was before.
**These approaches to life are definitely a deviation from the ‘traditional approach’ but I don’t personally align with them and therefore didn’t see the point of covering them in this post. I think the idea of retiring earlier (F.I.R.E.) by working harder & smarter is just a faster route to the same outcome that the traditional path gives you. Although I have a lot of respect for people who find this is the right path for them!
***One tenet that is consistent across both Adventurists & Masters, despite it not being obvious with the latter, is that growth is not linear. For both paths, there will be ups & downs. I’ve spoken to Masters who realized they were mastering the wrong thing, i.e. in in an industry that was dying or in a skill that had a low ceiling, and had to adjust. This is a key problem is hyper-optimization; looking for the biggest win in your next thing can limit your ability to discover something new that initially has low return but exposes much better outcomes.
