Trading Income for Time


How you can reverse a transaction you’ve only ever known to go in one direction

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School, then job, then bigger job, then bigger job, then bigger job, then financial independence and retirement. Maybe sprinkle in a spouse and kids along the way, a mental breakdown or two, but as long as we grow throughout the process then (we’re told) it’s ok. The painfully ironic piece of this equation is that the end game is gaining more ownership of our time, something we started with an abundance of.

Let’s say you live to be 80 (even though we know 100 is probably more likely for reasonably healthy millennials given modern medicine and health education). You spend the first 20 years controlled by your schooling and parents, the next 40 years controlled by your employers, and the last 20 years controlled by your health limitations. That middle chunk of 40 years must have SOME wiggle room, right? There’s an obsession in today’s culture to design our lives to our interests and ambitions rather than having the outside world do it for us, a worthy ambition provided it’s not a childish utopian delusion.

How do we find practical ways before the end of this journey to trade income for time when we’ve been so deeply conditioned to do the opposite for the entirety of our most vibrant years? It starts with understanding why we do it the way we do it today.

We have been taught, and even celebrate, a formulaic method of drifting through our lives

You know those stories and anecdotes about highly successful entrepreneurs who were B and C students growing up, only for us to discover years later that the confines and structure of the school system limited their true potential?¬† That wasn’t me. I’ve always been hard working and have found success, but generally colored within the lines to get there because that was the path I could see – the path to which working hard (the input) would result in success (the output). I went to a good college, went straight into an MBA program, and began a 10 year career in the highly lucrative San Francisco tech scene, jumping a rung up the corporate ladder every 2 years or so. My path has been relatively conventional – in a good way I suppose. This is what I’ve been taught success looks like.

The issue is that somewhere along the way, unless you blindly love the work, it’s easy to fall into the “going through the motions” abyss. We all face this in some capacity, and sporadically it’s probably fine. Facing it consistently for prolonged periods of time, however, almost always leads to some existential crisis questioning why you are doing any of this in the first place. By this point in your career, you have likely established enough of a financial safety net that it actually becomes a very fair question to ask.

The damage of trading too much time for income gets dangerously buried in secrecypexels-photo-278312.jpeg

What happens when you don’t address this type of purposeless grind for too long, working 70 hours a week on something that doesn’t make you jump out of bed in the morning? For me there was a point, difficult to pinpoint exactly when, where the physical and mental effects began to show their wear and tear. This included some of the predictable things like lack of focus and concentration, chronic fatigue, and the like. But it also included things that gave me some serious pause. A sense of apathy and dissociation toward things in my life and work that had significant repercussions. A sense of feeling out of your body only to watch yourself engage from someone else’s perspective. This generation, particularly within the tech industry, is obsessed with mindfulness, but it’s only when you start to drift too far in your own mindfulness that you realize why people work so hard to protect theirs.

If you’re a basketball fan, or even if you’re not, you may have noticed that Kevin Love of the Cleveland Cavaliers recently published an essay documenting his in-game panic attack and how it erupted from deeply unaddressed internal conflict. It’s a powerful post and one that points to the culture of hyper-competitive environments and upbringings. It transcends far beyond the sports world, surfacing the crippling inclination to bury mental health issues under the guise of being an unwavering team player. The descriptive excerpts from Love’s post that immediately froze me were “it was like my brain was trying to climb out of my head” and “it was like my body was trying to tell me ‘you’re about to die’. This is utterly terrifying, debilitating, and it can shift your perspective in the blink of an eye.

I fortunately have never suffered from a panic attack, breakdown, or any other incident of equal magnitude. Feeling on the VERGE for long enough, however, is your body violently screaming warning signs to make a change, even if short term. The simple thought of recognizing this and choosing to act in some capacity will lead you to find an alternative, as permanent or temporary as you so choose.

There’s an alternative, but it’s not cheap


I’m not one to tell you to follow your dreams no matter what. That’s nuts. If I did that, I’d start a fantasy football podcast with my league, generating a subscriber base never exceeding double digits even from friends and family due to the offensive content and utterly asinine tangents. That said, a passion project is a great idea when your livelihood doesn’t depend on it. I’m not taking a hiatus to brush up on writing and other priorities purely on a whim or to try to “go viral”. I’m taking a deep breath to re-energize after a decade of working to the bone and progressing to a point where maximizing income at all costs is no longer the North Star in designing and optimizing my life. When you can accept this choice as a process of improving your life and not one of bleeding money, taking a gamble becomes a relatively clear decision that almost surprises you in how long it took for you to act.

READ READ READ about personal finance

If you are even thinking about a major change to your money and time allocation, you have to understand the current state and strategy behind your personal finance to the extent that you can directly translate it to the risk you are willing to absorb. That includes asking yourself the following questions:

  • What will my resulting cash flow look like after trading income for time? If it’s net negative, I better be all in on where my newly found time is directed because it can’t just be a casual hobby at that high of a risk level.
  • What’s my net worth? What do I want it to be, realistically? How will a major life decision change the timeline in getting there and am I ok with it?
  • Am I readily equipped and comfortable with reducing my income all the way down to simply covering my living expenses, relying only on my existing investments INSTEAD of my savings rate to fuel future growth?

All of the above should guide your decision, and if you can make the leap you should have pretty concrete answers to each of these bullets.

I’m not trying to be a personal finance writer because there is plenty of material out there in that field as is, but understanding it is so inextricably tied to how you optimize your life that it only makes sense to highlight it where appropriate. A brilliant and inspiring book on the income vs time trade off is Vicky Robin’s Your Money or Your Life, a widely revered work originally written in the early 90s but revised for re-release in 2018. I highly recommend it to anyone considering a major shift in their own lives.

In unpacking some of the ideas from this discipline, one of the most basic concepts of personal finance is having an overarching strategy of wealth accumulation during your working years followed by a strategy of wealth preservation during your golden years, with your portfolio allocation of stocks and bonds shifting as you approach preservation to balance growth with security. Influencing¬†my own decision to take a break to focus on my writing, parenting, and general wellness, I believe my wife and I have graduated from pure wealth accumulation to a hybrid of the two (I may still need to convince her of this), which I have only validated after careful scrutiny of our family’s future – both in financial terms and in terms of quality of life.

Taking the leap fuels a psychological shift on day 1

Creating a basic, ugly blog. Starting an online business. Building a new company. Taking time off. Whatever the leap is that you’re taking, something changes in your brain literally the first day that you jump into it. It expands your way of thinking simply in acknowledging that there are more ways than one to find progress, to find personal growth, to let your reticence of telling people what you want finally fade. If this is the only thing you get out of taking some time for your own pursuits, it’s a win that you can carry with you into all future endeavors. Take advantage of it and see where it takes you. It might even lead you somewhere you’ve already been, just with different perspective and renewed purpose.

It doesn’t take long to hit the first wall of doubt

This is hard. We’re in a somewhat paradoxical time where starting independent work or chasing personal freedoms in any capacity is easier than ever, yet gaining traction seems impossible at the beginning. The psychological hurdle of starting is the first, and heaviest, domino. The idea to remember and anchor to is that motivation doesn’t just spark action – action sparks motivation. Redesigning your life to better serve your biggest obligations and aspirations takes consistency and getting your ass of the couch.

DECIDE you actually want to trade income for timecoins-currency-investment-insurance-128867.jpeg

You’re not a bad person for sticking with the big tech job for the money. You might have a family to support, a house to buy, or frankly just like buying shit you don’t need. No judgment from me. Figuring out that making the trade is what you WANT to do is the simple yet deeply personal and reflective decision that requires thought from all angles before pulling the trigger.

There are risks. It’s easy to say after the fact that you can simply trade your time back for income whenever you please, but that doesn’t happen with a snap of your fingers. As with anything, be deliberate with every decision you make, large or small. As long as you accept the opportunity cost of what you’re not doing, you made the right choice.


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