I Finally Enjoy My Work

For the first time since probably my junior year of school at Ivey, I can say that I feel motivated and excited about my work and my life. I finally have authentic goals that I enjoy working towards and feel like I have some mild sense of purpose.

There was a long stretch of time – essentially the full four years after I graduated from university – when I abandoned all hope that I could ever be happy with work.

I had derived so little joy from my job that I resigned myself to this idea that I would always have to accept some suboptimal combination of work, hours, and salary. In fact, reading through my 2018 annual report (the precursor to this blog), I saw that one of my main life goals was to to simply “not hate my job”.

An excerpt from my 2018 “Annual Report”

At the time, asking for anything more seemed greedy and self-entitled.

And perhaps it’s just the naivete of my first year of “entrepreneurship”, but I really enjoy how things are right now.

Despite the physical stagnancy and social reclusion of the year, this is very likely the happiest I’ve been since graduating school. Honestly, this is potentially the happiest 12-18 month period in my life so far (the contender probably being my fourth year at Ivey, with grade twelve as a nostalgia-glazed dark horse).

To my pleasant surprise, I’m beating my year 1 income target while working an average of 15 to 25 hours per week. I was working 40-50 hours per week when building the bulk of the course, but the maintenance level of effort required is not that much.

I also get to spend lots of time with my amazing girlfriend and on my non-work interests. I no longer get that uncomfortable existential dread on Sundays and overall I feel maybe 5% as stressed as I did while working in finance.

One thing about happiness – it’s not so much that I wake up every day elated and smiling wide like some kind of beloved cartoon sponge. It’s more that there are much fewer troughs and stress points in my life. No more unpredictable late nights or grimacing at the sound of an email. For me, becoming happier was much more about eliminating sadness as opposed to chasing highs.

I also confidently hold the belief that that the future is going to be better, which I didn’t genuinely believe before. I’m still afraid of growing old and dying, but I have this optimism that my early 30s are probably going to be more awesome than my 20s.

Talking about all this might come off as bragging, but

• a) Well, this is my blog.
• b) I think it’s valuable to share genuine wins when they happen. It’s also not like I accidentally stumbled into this situation – this is the result of years of research, risk taking, and hard work.
• c) I want to remind people who hate their jobs that alternatives do exist. Work isn’t supposed to be intrinsically awful, I think it just gravitates towards being awful if you don’t have any control.

Now, I’m still not making as much as I did in finance, but I’m covering all my base needs / wants and I believe there’s a path to more upside.

What Do I Actually Do?

Very good career advice I received a few years ago was to think carefully about the specific tasks I wanted to spend my time doing every day. I think it’s very easy to idealize a job for its function or focus on its external benefits without regard for the actual tasks you have to do.

You can love education, but if you dislike supervising kids, you probably wouldn’t be a very good school teacher. You can love art, but if you dislike working with clients or having to self-promote, you might not enjoy doing art as a job.

I was drawn to finance because I enjoyed the learning and gambling aspects of investing. But upon working, I discovered that I didn’t really enjoy the legal, process, or diligence portions of it. And it turns out that the majority of your job is diligence and process (especially in private equity).

For Peak Frameworks, the major functions of my “job” right now can probably be categorized into one of:

1. Creating educational materials
2. Marketing and selling educational materials
3. Administrative and support tasks

To give you a better idea of what this actually entails, below are the specific tasks that I find myself doing on a weekly basis. I’ve tried to rank all of the major tasks I do out of 5 (with 5 being the most enjoyable). I’ve ranked them all based on my enjoyment of them, as well as how important they are to the business engine.

Most of the time, I’m pretty happy with the tasks I do for Peak Frameworks. I enjoy explaining concepts concisely and clearly, so creating course content and YouTube videos is fun. I still have to do a decent amount of “$10 per hour work” like answering YouTube comments and replying to e-mails, but everything is still pretty manageable.

I’m lucky to have a pretty broad set of responsibilities, so I can also focus on a different area of the business if something feels stale.

In contrast, I would rank most of the tasks at my prior jobs at about a 1 or 2 for enjoyment (and possibly also a 1 or 2 for importance…). In hindsight, the only thing that I consistently enjoyed in finance was going to management meetings and doing expert calls, which is when you got to ask industry experts anything you wanted.

I also think that context of a task matters a lot. I actually enjoy financial modeling if it’s at my own pace and it’s not heavily scrutinized. I find that it’s really hard for modeling to be fun when you have to build it on an extreme time deadline with multiple iterations.

The Temptation to Advertise More

There is one interesting “moral hazard” of the business that I’ve had to keep an eye on. There is definitely a temptation to focus much more on advertising rather than product quality, because you might be able to make more money that way.

Once the course content is fully made, there isn’t really an impetus to update the content or improve the product. Oftentimes, it’s more profitable if I make a good promotional YouTube video as opposed to making another case study or model template.

Sal Khan, one of my role models and creator of Khan Academy, described this well on How I Built This:

It’s pretty evergreen content. If once you have a good explanation of adding fractions with unlike denominators, pretty much everyone in the world could use it. And you don’t really have to refresh it unless you figure out a better way of explaining adding fractions with unlike denominators.

Sal Khan via NPR’S How I Built This

Luis von Ahn, also on How I Built This, described this phenomenon more directly while speaking about Duolingo.

A lot of companies in education eventually turn into marketing companies. For the following reason: you realize making improvements in how well you teach is hard. And it really is very hard. It takes years. So, for every dollar you have, you quickly realize that it’s actually better to spend your dollar marketing your product rather than making your product better.

Luis von Ahn via NPR’s How I Built This

There is definitely a temptation to focus more on advertising rather than improve old products or roll out new features. I think a lot of prestigious schools and universities suffer from this too to be honest – it seems that some are more focused on rankings and reputation vs. the actual student experience.

I want to make sure that I always prioritize learning and teaching people. We’ll see how viable this virtue will be to uphold as I continue to grow the business.

You Should Try Something Too

If my work situation is something that entices you, I honestly think that you should try and build something yourself.

I don’t think full “entrepreneurship” is for everyone, but I do think that most very smart people I know tend to underestimate themselves.

I’ve personally found this year to be extremely fun and I don’t think “entrepreneurship” has to be an all-or-nothing proposition. Building something small can give you the confidence and exposure to pursue something larger down the road. For example, I don’t imagine that Peak Frameworks is going to be the only entrepreneurial thing I do in my life, but it’s helped me realize that I really like this setup.

Realistically, you probably need to do some form of digital entrepreneurship (information content, e-commerce, consulting, software engineering) if you want to have the specific combination of elements that I have (hours, remote, no boss), but that’s still a very wide range of possibilities.

I’ve only worked in finance (where most people are extremely intense), but I would guess that pretty much everyone I worked with had the intelligence and drive to build something successful. Most people I know that have pursued the search fund route are doing extremely well. Most people I know that have pursued entrepreneurship and have stuck with it for a few years have also done well.

Of course, I’m still leaving tons of room for error.

There is a good chance that my business is unable to produce a consistent stream of revenue (I would guess either due to piracy or competition). There is a high likelihood that I only like things now because they’re fresh and new.

There is also a very high chance that the exponential growth in the salaries of my old finance coworkers will start to gnaw at me.

But for now, I’m happy. And I think it’s foolish to try to overthink things when you’re happy. Overthinking is something you do when you’re sad.