Take Retirement in Little Batches

It’s really not a problem—and certainly not a failure—to run a firm for a few short years and then move on. Most of you are supremely talented, and this path you’ve chosen is just one of the many ones where you could have been wildly successful.

On the other hand, why not run your firm in a way that you can do so indefinitely? My friend John Warrillow wrote Built to Sell, and that’s exactly the point: run it as if you want to maximize a sale, and in doing so, you’ll feel the least amount of pressure to sell it because you’re having so much fun, making so much money, and having such a significant impact. We talked about this in a 2Bobs episode, noting Blair’s suggested constraint: if you tell yourself that you can never sell it, you’ll run it differently.

Earn the Right to Work

The other concept he introduced in that episode was this: you don’t work in order to earn time off, but you take time off in order to earn the right to work. That’s a really powerful notion.

I want to expand on that a little bit by adding this: take your retirement in stages and not in one big, uncertain, lonely, poor option at the end.

We’ve Got Retirement All Wrong

Seriously, what in the heck are we thinking with the normal way of doing things? Work your butt off, assume there will be a pot of gold at the end of the rainbow, and then move away from all your friends to Florida? Count me out. I’m not opposed to Florida as much as this silly notion that we keep pushing real living out in front of us, like an inner tube in front of a container ship. Always out of reach, but visible to torture us.


  • You have more money now than you might later. If that’s not true, better fix it. The only money you can count on is the money that you pay yourself every regular payroll.
  • Statistically, your health is better.
  • The team really needs you to have a life. Your intensity is a bit much.

So, like Emily shows in the illustration, take it in batches, and the beginning of the year is the best time to plan for that. Get the dogs taken care of, make reservations, and block it off on your calendar. I do client calls Monday through Thursday, and I take off one week for every three that I work. It’s how I maintain my sunny disposition. (No comments, please.)

It’s Time To Talk About Time

But let’s talk about time for a minute.

Morgan Housel, one of my two favorite financial thinkers (the other being Carl Richards), said this:

“The highest form of wealth is the ability to wake up every morning and say, ‘I can do whatever I want, when I want, with whom I want, for as long as I want.’ This, more than your salary, more than the number of your hours, more than the prestige of your job, more than anything, is the highest dividend money pays.”

Amen to that. It’s not as if we’ll get far without goals and the discipline to accomplish them, but you do not have a boss, and it’s crazy to live life as if you do. But the main inference I’m going to draw from his quote is this: money is time. We’re used to thinking that time is money, but it’s really the other way around. Money is time. Money is time. Money is time.

Money is how we tend to measure respect, too, but I don’t think that should be the case. Here’s Peter D. Kaufman with a similar angle:

“We tend to take every precaution to safeguard our material possessions because we know what they cost. But at the same time we neglect things which are much more precious because they don’t come with price tags attached: the real value of things like our eyesight or relationships or freedom can be hidden to us, because money is not changing hands.”

This, too, was a new concept to me: at a young age, we have no money, but we have billions of seconds. Listen to Graham Duncan of East Rock Capital (and thus someone who knows a little bit about money):

“A million seconds is 11 days. A billion seconds is slightly over 31 years…. I feel like in our culture, we’re so obsessed, as a culture, with money. And we deify dollar billionaires in a way…. And I was thinking of time billionaires that when I see, sometimes, 20-year-olds—the thought I had was they probably have two billion seconds left. But they aren’t relating to themselves as time billionaires.”

You may find the idea of a “Memento Mori Life Calendar” morbid, but I like how it focuses my mind and so I have one…and crossing out every week puts things in context for me. Like the illustration, life is best lived in lots of short little chunks. Don’t bunch all the fun ones up at the end.

Shopify extends this concept to meetings, translating time into money. Now there’s an idea!

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