The Problem with a Comfortable Career

A framework for assesssing and re-evaluating things when your work life is just a little too easy.

Have you ever found yourself worrying that your life or career was a little too comfortable? And then maybe immediately felt guilty because of how privileged a problem that is to be able to have?

This post is for anyone who—like me—has ever asked themselves the question: is everything just a little too easy?

I drafted this piece from the 13th floor of a Bangkok condo looking out over a beautiful, modern and foreign city. I had spent the previous week in Chiang Mai hiking mountains, exploring temples, and eating some of the most delicious—and cheapest—food I could imagine.

Bangkok Airbnb

The view from where I drafted this post. Bangkok, Thailand.

From Thailand I flew back to Cape Town—arguably one of the best cities in the world—where I returned to my current life of working 30 hour weeks, messing around on side projects, hiking and running in the hills, and surfing in some of the better conditions that exist on the planet.

I am ridiculously fortunate. I want that to sink in.

Having acknowledged my own privilege, we can now dive into the more complex and nuanced problem I’ve been wrestling with lately: the idea that things right now may be a little too good.

Too good?” you ask. “Isn’t that an oxymoron?

It’s true. “Good” isn’t the right word, exactly. More like “too easy”. Or “too comfortable”.

The problem with living a life of comfort is stagnation. What happens when we get to a comfortable place is that we decide we like it and we want to stay there. Possibly for a long time. Possibly forever.

But when you’re comfortable it’s also likely that you’re not really challenging yourself. And when you’re not challenging yourself you may not be fully realizing your potential. And then forty years go by and you find yourself sitting in a retirement home wondering if maybe you should have done something more ambitious or inspiring with your life. Maybe.

Mossy Stone

They say rolling stones gather no moss. But if stones never got comfortable then moss would never have anywhere to grow.

Facing Comfort in My Career

Let me explain a bit how I got here.

So last year, facing high stress levels and burnout I decided to take six months off to figure out my next steps—which included trying to launch software products, freelance consulting, and seeking out a career I loved.

Towards the end of that period I came up with a plan that I thought was foolproof. I could have it all. I’d continue building and selling products, work part-time for an organization I loved and believed in, and fill the income gap with interesting freelance consulting work. All while working a totally manageable number of hours—leaving plenty of time to take care of my body and mind.

And the plan is working. A little too well.

So now—living what amounts to a great life by any standard—I keep questioning the wisdom behind this plan. Was optimizing for a life of balance and day-to-day happiness the right call, or should I be more proactive about dedicating myself wholly to a more focused purpose—and willing to accept the day-to-day effort and stress that comes with that?

I don’t have those answers today. In fact, I would guess that I will—and many do—spend an entire life searching for them. What I know to be true today is that I’ve been feeling stagnant—like I’m not learning or growing nearly as much as I could be—and that I’d like that to change.

What are you optimizing for? Your career as a specification.

As I try to figure out what to do next, I keep coming back to a notion I embraced last year of designing one’s life.

Being a bit of a nerd/engineer it helps me to think about my future in terms of engineering that design—a.k.a. a specification. What are the important requirements? Nice-to-haves? Key tradeoffs?

For example, if I were writing the specification for my career, the key requirement would be enough income to live comfortably on. Some key nice-to-haves would include work I enjoy, work-life balance, making an impact, and personal growth. My current situation performs great on some of these axes, but less great on others.

The complication is that—like most design/engineering decisions—the different axes trade off against each other. Investing deeply in your work creates the greatest opportunity for impact, but also might lead to the worst work-life balance. Like any good product manager would tell you, you just can’t have it all—you have to choose what you’re optimizing for and make a series of trade-offs that align with that decision.

Facing the future—charting a new course

Applying this framework back to my own life, I’ve currently nailed enjoyment and work-life balance, but I’m falling short on impact and personal growth. Plotting these out, it might look something like this:

Current Situation

How my current career scores on my four desired “career axes”

My current crisis of comfort seems to be my subconscious telling me that it’s time to make strides on personal growth.

So I know that I’d like to increase the number of challenges and growth opportunities in my life. Ideally, I’d like to be able to do that without sacrificing on enjoyment or work-life balance; and of course I’d like to make as much of a positive impact on the world as I can. I also know that achieving all of that will be impossible, so instead I’ll have to choose from some different possible paths—each with their own upsides and downsides.

The rest of this post applies specifically to my own situation, but I’m hoping that seeing someone go through the thought process might help you think how to apply it to your own career.

Path one is to double down on passive income.

In this world, I stop thinking of my side projects (Place Card Me, Chat Stats, and Build With Django) as side projects and start thinking about them as my path to financial freedom.

There is a huge amount of opportunity for personal growth and challenge in pursuing this path. In the last year I’ve successfully launched two revenue-generating projects, but I haven’t come close to figuring out how to grow them to sustainable-income levels.

Investing in this path might result in me trying harder to build a business-to-business (B2B) product, or perhaps publish an e-book or a course—both things I have considered, but approached half-heartedly to date.

In focusing harder any of these things I would expect a high amount of discomfort, and, conversely, growth. At the same time this path might score poorly on the axes of enjoyment and impact, which is why I’ve largely resisted it to date.

Passive Income

How pursuing passive income projects might score on my four career axes. High on growth but low on impact.

Path two is to invest more in my job(s).

A downside of working on your own is that it often limits the amount of impact you can have with your work. Working for an organization whose scope and mission is much greater than that of a single person is a good way to amplify that impact.

On top of that, my current paid work is actually where I feel that I’m learning the most right now—and possibly where the hardest problems lie. Some of these problems are technical—e.g. designing a scalable and sustainable reporting architecture for the world’s most powerful mobile data collection platform. However, some are also complex human problems around people and organizations.

There’s no doubt that these problems are hard, and there is definitely opportunity for me to grow through this work. However, it’s less clear whether that growth would be in the areas I want to prioritize, how much I’d enjoy it, and most importantly, how hard it would be to maintain my current work-life balance in this world.

Working for Others

Working for others scores higher on impact, but worse on work-life balance.

Path three is an attitude adjustment on my current trajectory.

I mentioned at the top that my current career path feels a bit like coasting. Reflecting on that more, though, it’s clear that there are plenty of opportunities for challenge, it’s just that I’m not wholly embracing them.

This path proposes a subtle—but I hope, important—psychological shift; one where I continue to do the same type of work as I’ve been doing, but just embrace it harder.

It’s the difference between “I’ll let Place Card Me slowly grow as it will” and “I am getting Place Card Me to $1000 monthly revenue this year.” Or “I’ll trade my time for dollars on this consulting project” to “I’m going to build the best damn data system I am capable of with all my energy.”

Hopefully this adjustment will preserve the strong enjoyment and work-life-balance attributes I currently have, while improving personal growth (and acknowledging a continued sacrifice on impact).

Attitude Adjustment

An attitude adjustment on my current trajectory continues to prioritize work-life balance and enjoyment while hopefully improving the personal growth axis over my current trajectory.

Weighing these different plans against each other, I’ve decided that this last option is the optimal short-term course of action to take. So that’s my plan!

I’m hoping that this subtle-but-real attitude adjustment will be sufficient to kick me out of my current crisis of comfort and back into a world where I’m uncomfortable, scared, and growing again (including incidentally, the act of publishing a piece of writing—what you’re reading now—for the first time this year).

Let’s see how it goes.


As always, thanks for reading, and I hope that something in here helped you think through your next moves in your career or in life! If you want to see how it goes for me you can subscribe to get updates below.

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