In Praise of the Low-Income, High-Purpose, High-Freedom Career

While considering where to take my career at age 36, I consistently find myself balancing three factors: Income, Purpose, and Freedom. In this blog post I share the notes I’ve written to myself on this subject.[footnote]These are just my notes, not a fully coherent argument. I realize that there are many blind spots in what I’m presenting. I’ve done my best to note caveats in footnotes like these.[/footnote]

The Three Scourges of Modernity

In developed western countries, I think many of us suffer from:

  1. Owning too much stuff
  2. Not having enough free time
  3. Doing dumb (non-puposeful) work

Buying too much stuff is a result of (1) having a lot of money and (2) keeping up with the Joneses / running on the hedonic treadmill.

Not having enough free time is a result of working too much.

Doing dumb work is, unfortunately, the default state of the world. The opposite is purposeful work, and it’s hard to come by.[footnote]It’s also a relatively modern expectation. But it’s here to stay.[/footnote]

But, Security!

Most people’s primary drive is for security. Money and possessions lead to comfort and security. Free time and purposeful work don’t. That’s fine for them. It’s not for me.[footnote]I say this from a position of privilege, of course: I’m able-bodied, mentally healthy, not caring for dependents, not in debt, a citizen of the United States, and not dealing with repression due to my race or other factors.[/footnote]

With security as the ultimate goal, the standard metrics of success become:

  • Money earned per year[footnote]Here “money” includes benefits, i.e. employer contributions to healthcare and retirement accounts. They’re just another form of money, after all.[/footnote]
  • Vacation days per year
  • Hours of work per week

That leads us to say things like this:

She has a great job. She makes $70,000/year with benefits, gets three weeks of vacation, and works 40 hours a week.

The Dark Side of the “Great Job”

But that “great job” doesn’t account for many other potential factors. What about…

  • her crowded, stressful commute
  • the fact that she’s sitting inside all day
  • the cost of commuting, wearing appropriate clothing, and joining coworkers for drinks
  • the cost of rent she must pay to live close to her job
  • her unpaid (but expected) work on evenings and weekends
  • the fact that she can’t leave her job for more than three weeks
  • the fact that despite her high income, she may be hardly saving any money
  • the fact that she has little time to exercise, be outside, or pursue hobbies
  • the fact that she may not have any meaningful connection to her work, or even feel that it does harm to the world
  • that fact that for the majority of her waking hours, her life is controlled and directed by others

A “great job” might actually be a terrible job in terms of:

  • freedom: having enough time to pursue your non-career interests, spend time with friends and family, go on adventures, work on side projects
  • physical health: not constantly sitting; enjoying ample time for exercise and the outdoors
  • mental health: not being constantly stressed and anxious; enjoying a sense of autonomy and an internal locus of control
  • purpose: feeling like you’re making a positive contribution to the world
  • wealth: accruing savings; avoiding debt[footnote]Yes, buying a home may still be a good form of debt. But for a 30-year loan of $300,000 at 5% interest, you’re also paying $280,000 in interest. Just saying.[/footnote]

If we lump physical & mental health into the “freedom” category, then we really just have three variables to play with:

  • Income
  • Purpose
  • Freedom

Let’s see how a variety of jobs perform on these three metrics.[footnote]The following charts are 100% arbitrary and based on my (surely flawed) observations and assumptions about various careers. I have no doubt that there are corporate lawyers who find deep purpose in their work and organic farmers who lead high-freedom lives.[/footnote] (All illustrations by the author.)

Income vs. Purpose

For high income and high purpose, it’s great to be a doctor, professor, or the owner of a business with a social cause.

Corporate lawyers might make tons of money but feel dead inside.

The starving artist might be doing highly purposeful work, but they can barely afford to eat.

It sucks to work retail.

Income vs. Freedom

For high income and high freedom, it’s still great to be a professor or the owner of a social enterprise. If you own a 4-Hour Work Week style freedom business (designated as “4HWW”) that generates passive income, that’s great too.

Doctors, corporate lawyers, and techies might earn a lot of money, but they’re working their butts off, too. They can’t easily choose to work part-time for the same high hourly rate.

Working on an organic farm or at a small non-profit, you’ll probably have long hours and won’t earn much.

Purpose vs. Freedom

Successful writers, tenured professors, and the owners of social enterprises (the day-to-day tasks of which they can delegate to managers) seem like the big winners in Purpose + Freedom. Starving artists, too, although their freedom is curtailed by low income.

Those 4-Hour Work-Week “freedom business” owners might be living in Thailand but they’re probably not doing work that feels purposeful (e.g. drop-shipping Amazon products).

Working for a hot tech startup might feel moderately purposeful (“we’re gamifying puppy adoption!”) and you might go to Burning Man each year, but fundamentally you’re still working 70+ hour weeks.

Sorry retail.

In Praise of the Low-Income, High-Purpose, High-Freedom Career

There’s no silver bullet. Different people find satisfaction with different careers.

For me, the ideal combination is a career that earns me:

  • a low-to-moderate income
  • a high sense of purpose
  • extremely high personal freedom

With these as my priorities, the old metrics (income/year, vacation/year, hours/week) don’t make sense.  I should replace them with:

Income metrics
  • Income per hour (i.e., hourly rate)
  • Savings accrued per year
  • Interest payments per year (ideally, zero)
Freedom metrics
  • Hours that I must work per day
  • Days that I can totally avoid working per month
Meaning metrics
  • Life goals accomplished per year
  • Relationship quality per year (both building new relationships + maintaining/deepening old ones)


This is a lot to achieve. Below is what I think I need to do (and continue doing) to attain this lifestyle.[footnote]I’ve written this in prescriptive format—i.e., as advice—but please remember that I’m really just giving advice to myself.[/footnote]

Keep your expenses low
  • Enjoy cheap hobbies, like trail running ($) instead of skiing ($$) or going on fancy vacations ($$$)
  • Do work that pays for your life expenses whenever possible (e.g., when Unschool Adventures trips cover my room, board, and travel)
  • Don’t do or buy expensive things just because your friends are doing them
  • Continue hanging out with friends who prioritize freedom and purpose
Create work with a high hourly rate + low total hours
  • This is really hard. You’ll probably never find a job that offers this—you’ll have to create one yourself. Entrepreneurship for the win! (For me: this is Unschool Adventures)
  • Use your free time to pursue other high-purpose-but-unpaid pursuits (for me: writing, podcasting, public speaking), some of which may develop into new forms of income
Do stuff that feels purposeful, totally unrelated to career
  • If you don’t have any interests or hobbies that you pursue for their own sake, then this article will probably mean nothing to you
  • “Purpose” comes from connection to a community, connection to the natural world, service to a greater cause, or enjoying a flow state (For me: partner dancing, wilderness backpacking, and advocating for self-directed learning)

That’s how I think about my career. That’s all I’ve got.



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