How to Make Terror-Free Career-Defining Decisions
Living well does not mean avoiding suffering; it means suffering for the right reasons. While pain is inevitable, suffering is always a choice.
The most meaningful freedom in your life comes from your commitments, the things in life for which you have chosen to sacrifice.
Mark Manson, Everything Is F*cked
In 2018, I walked out of the Shoelace offices and started my own business. I swore that that would be the first and last full-time job I’d ever take. But then in July 2020 — almost exactly 2 years later — I signed on to start full-time at another tech startup called Convictional.
What changed? Well for one, I’m older and wiser. I’m no longer a new grad trying to figure out what I want to do. I’ve been at at least 5 companies — including my own! — and now I know what I want.
This said, making a decision like a career change still involves uncertainty.
Doubt.
Fear.
So how do you make decisions when there’s a world of ambiguity and there are no right answers?
As Pierre-Marc-Gaston says,
“Judge a man by his questions rather than his answers.”
In this article, I’ll walk you through 5 simple questions I use for most major life decisions.
If you could only have one singular reason to do this, what would it be?
Does this opportunity give you more opportunities?
What do you really want?
Does this allow you to solve problems you want to solve?
Does this allow you to solve problems only you can solve?
I hope they help you as much as they help me.
A short message before we dive in: I usually write about web3, creativity, and the creator economy. If these interest you, you’ll probably enjoy my weekly newsletter. Subscribe below to get more posts, or check out previous editions to “try before you buy”.
Question 1: If you could only have one singular reason to do this, what would it be?
Knowing your single primary reason is the key to accepting or rejecting an opportunity. For example, when I was deciding whether or not to buy an iPad and an Apple Pencil, I asked myself why I wanted an iPad. The answer was, “I want to write in my journal by hand and make it searchable.”
An excerpt from my GoodNotes 5 journal
Sure, there are cheaper Android tablets that let me watch Netflix and read PDFs on a bigger screen. But if my singular use case is to write? No Android tablet comes close.
Knowing this helped me make the decision to buy a used iPad Pro & Apple Pencil from a friend for $400, versus a brand-new iPad Pro for $1,000. Because I got the iPad used, I could pay extra for premium items like GoodNotes 5 and Paperlike 2 — purchases that are essential to my use case. A singular overarching reason helps hash out everything, including the minute details.
Once you know your primary reason, you can decide whether or not it lines up with your values. Your values are what you prioritize over everything else.
What is the fulcrum that your decision-making hinges on?
For example, one of my values is mastery — being the best in the world at something. Like any modern knowledge worker, I also value freedom, but not as much as mastery. In line with this, here’s what I told the Convictional team: the only thing that would get me to drop my business would be the opportunity to become the Andrew Chen or Brian Balfour — two of the top growth marketers in the world — at an up-and-coming tech startup, preferably in ecommerce or direct-to-consumer (DTC).
Marketing has been an enduring interest for me. It plays to my personality and strengths. It demands a balancing act between art and science, left brain and right brain. And so, if there was one singular reason I’d trade my business/freedom, it’s to master marketing at the most difficult level, without the distractions of client work or cashflow.
Finally, when the going gets tough, your primary reason is what you’ll come back to. For me, it’s asking if the job is still helping me become world-class at marketing. If it is, I’ll keep pushing through the problems. If not, then it’s time to reevaluate my career. As Mark Manson says in his book The Subtle Art of Not Giving a F*ck, “To not give a fuck about adversity, you must first give a fuck about something more important than adversity.”
Question 2: Does this opportunity give you more opportunities?
One of the biggest misconceptions people have is that specialization boxes you in. It doesn’t. What actually boxes you in is a misunderstanding of what opportunity costs are. Most people forget to factor the cost of giving up the next-best choice into their decision-making.
Brian Balfour put this well in his article “7 Principles to Mastering Growth,”
“Most real world work involves a problem that doesn’t have an answer yet, and the biggest growth opportunities are in uncharted territories.”
In contrast, there’s no reward for risk-taking in client work. My retainer and my rep are on the line. I’ll stay within “charted territories” and work with clients whose problems I already have the answers to.
At Convictional, I’ll break new ground, looking for opportunistic channels that have short-term gains and long-term promise. My main mission is to quickly test paid, earned, and owned marketing channels for the company. Long term, I need to build a marketing flywheel that will compound those wins over time.
The opportunity cost of being a generalist, of having a hand in different cookie jars, is that you won’t have the time, the attention or the energy to pick out the one cookie you actually want to eat.
Committing to a single field means you reject all other alternatives. The reward for ruthless commitment? You get specific opportunities related to that field. Opportunities that wouldn’t otherwise present themselves to dabblers and beginners.
“Take a simple idea and take it seriously.”
Charlie Munger
Another thing I can’t do with my business is build a world-class team. Because I’m still so early in my career, none of my previous employers or clients have tapped into a secret superpower I have: I can read 80% of the people I meet like a fiction book, instantly and accurately. In fact, I’ve been accused of being a mind-reader like Donna in Suits.
I can only exercise this strength if I’m looking to hire top performers.
Question 3: What do you really want?
Now you know why you should take an opportunity (#1) and whether it’s actually worth taking (#2). It’s time to zoom out to higher-level territory.
Freedom is having a some level of each of these
You want to make sure that the opportunity doesn’t just give you more stuff to do, but that it lets you do what you want to do. This is about knowing your values and principles. And knowing what you will and won’t compromise on in terms of time, energy, and money.
Time — Are you looking for flexible working hours and location independence?
Energy — How much stress are you willing to take on?
Money — How much are you looking to make each year? How did you get to that number?
It’s easy to say what you don’t want. It’s hard to articulate what you do want.
If you start your own business for more freedom, are you willing to work holidays and weekends?
If you want a low-stress job, are you willing to have less financial stability?
If you want to make $500,000 a year, are you willing to put in a disproportionate amount of effort into your business or into your career?
It took one summer co-op term for me to be certain that I didn’t want a stuffy corporate job. But to articulate that I want to work at a tech startup at the aggregator or platform level? That took another 7 years, overlapping 6 years of writing online, 2 years of running my own business, and 16 months of work terms.
From a values and principles perspective, it’s easy to say what you won’t compromise on, but hard to articulate what you actually stand for. If my highest ambition was to be a lifestyle entrepreneur, sipping coconut juice in Boracay while running my dropshipping store, I don’t have to be the first marketing hire at a startup with IPO potential to achieve that.
But becoming a lifestyle entrepreneur is not my dream. Like Harvey Specter, I know what I can do. And like him, I say:
Unlike lifestyle entrepreneurs and digital nomads, I’m not optimizing for freedom of location and time. I optimize for intellectual reinvention, boundless mastery, and high-impact problem-solving.
Speaking of problem solving, skills- and compensation-wise, there’s no higher playing field for a business to go than at the marketplace level. Or, as Ben Thompson calls it, the aggregator/platform level.
Courtesy of Nathan Barry’s wealth ladders illustration, that’s where I’m going:
To this:
I’m an obsessive, voracious reader who can’t stop learning once a topic interests her. I’m also a nerd who works best when both sides of her brain are used. In optimizing for mastery, I give up some of my freedom to put myself in a position to maximize who I am and what I can do.
If you base your life decisions on crystal clear personal values, you stay true to who you are. Otherwise, you deceive yourself and pander to other people’s decisions, motivations, and values.
Question 4: Does this allow you to solve problems you want to solve?
I don’t know if you’ve noticed this, but I haven’t talked about happiness in my career, at all. Nowhere in my decision-making does happiness come into play.
As Cal Newport points out in his seminal career book, So Good They Can’t Ignore You, fulfilling careers are built on three things:
Competence — how good are you at what you do?
Autonomy — how much freedom do you feel you have at work?
Relatedness — how connected do you feel to the people you work with?
I wasn’t optimizing for wealth or freedom when I signed the contract. My only financial requirement was that I make enough to rent my own place in Toronto. Once that was settled, I willingly conceded my self-employment benefits — laptops by the beach, pina colada’s, and a sun tan in February.
But just between you and me, I don’t feel like I gave anything up at all.
Working at Convictional removes the impact, reward, and difficulty ceilings for my career. Working at a company frees me from distractions like cashflow, bookkeeping, and client pipelines that take my attention away from a singular goal — marketing an IPO-worthy idea. The company is also (thankfully) 100% remote so I’m still in charge of my own schedule.
I’m pumped. I’m free to pursue the most challenging marketing problems in the world… Problems that also hold personal significance for me and my family.
To get here, I gave up a little bit of what I valued less (freedom) for what I deeply love (mastery) — how is that a sacrifice?
Happiness and success in a career (or in life!) don’t hinge on “following your passion.” Happiness is a by-product of choosing your poison. You achieve happiness by forgetting about it, and instead choosing the pain and problems that you want for yourself.
As Cal writes,
“The focus shouldn’t be on passion, but on skills. The way you build skills is by tackling progressively more challenging problems.”
Taking this job at Convictional is my dream job, not because I’ll "never work a day in [my] life." I didn’t say yes because I don’t foresee problems. In fact, this job terrifies me because it’s going to be a lot of work, a lot of failure, and a lot of headache.
But I know this move give me more joy and meaning, because it lets me obsess over problems I want to deal with, while eliminating ones that I don’t.
Question 5: Does this allow you to solve problems only you can solve?
If you want to carve out a name or a personal brand for yourself, you have to obsess about being the go-to person to solve a particular problem. To remove yourself from everyone else trying to solve a particular problem, the path of least resistance is to obsess about problems only you can see.
Entrepreneurship is about developing valuable ideas around knowledge that other people don’t have. It’s about executing against secret information and a different set of knowledge corridors than other people.
Here’s a secret most people don’t know: The highest value deals in business don’t come from business-to-consumer (B2C). They’re all found in business-to-business (B2B) transactions.
B2C companies — even less mainstream ones like Corkcicle, and Muji — hold all the sex appeal. They have to appeal to the masses with attractive branding. Otherwise, they don’t grab attention. They can’t compete. They don’t sell.
But it’s in the B2B world where the most lucrative deals hide. Sure, deals take more time because B2B is notoriously bureaucratic and can be frustratingly nepotic. But once you’ve built that relationship and struck that deal, you have it made.
You have a financial runway.
You get volume purchase orders.
You negotiate manufacturing terms with economies of scale.
It’s this insider’s knowledge of the untapped frontier of B2B ecommerce that serves as Convictional’s unique selling point. Convictional aims to help speed up that process of B2B relationship-building and deal-making.
When it comes to career decisions, you have to factor in your interests and how you can be the best in the world at what you do. Like Scott Adams advises, you don’t have to be #1 at one thing to assure you made the right decision. All you have to do is position yourself at the top 25% of 2-3 skills and make that unique stack your value proposition to the world.
Why I’m OK Giving Up My Freedom to Work at a Job
Jim Collins’ Hedgehog Concept in Good to Great, is one of my all-time favourite decision-making models for major life changes.
Asking “What do you really want?” fills in the Economic Engine circle
Asking “Does this allow you to solve problems you want to solve?” fills in the Passion circle
Asking “Does this allow you to solve problems only you can solve?” fills in the Word-Class Skill/Potential circle
If you’re not sure what the right answers are, don’t worry about it. As fallible human beings, none of us can make the 100% correct decision each and every time. In any kind of decision-making we make, we have to accept that we can never be perfect, but only less wrong.
The problem compounds when we chase happiness and make decisions based on ease and comfort, instead of chasing commitments and picking what problems we want to have.
If you recall Cal Newport’s 3 factors of a satisfying career (competence, autonomy, and relatedness), he takes a similar approach. The focus is on skills, pain, and problems. Not happiness and ease. Nothing about comfort. Or pleasure. Or hope.
That’s a hard pill to swallow. And these questions are designed to help you move from a mentality of happiness/passion to pain/problems. And to make that switch easier.
Ironically, going deeper into a field and taking on tougher problems automatically produces happiness and comfort as by-products. Because, as Mark Manson eloquently puts it, “when you give better f*cks, you get better problems. And when you get better problems, you get a better life.”