The Lies Founders Tell About Retirement

Retirement is a beautiful lie we Founders tell ourselves.

We fantasize about one day selling our startup, retiring, and living this gifted life that makes all of our sacrifices worthwhile. We see this perfect existence that was only constrained by the shackles of our work and the drudgery that was our startup.

Yet it turns out while it may be a fantasy for us, many enterprising Founders before us have actually playtested this fantasy for real. As it happens, nearly all of us develop some version of the same fantasy and later on come to the same (much more sober) reality.

It turns out, it's really easy to tell ourselves what we're going to do when we retire, but actually doing any of that stuff is harder than building the startup it took to get there to begin with.

"I'm going to read like crazy!"

That stack of books that we ordered on Amazon and never read are finally going to get their cozy date by the fireplace we promised them. We're going to burn through all of those stored up Audible credits in a week. There won't be a single interesting Medium post we won't have combed through in detail. Hell, we're even going to write some genius comments!

But you know why we weren't reading like crazy before? Because it's not that much fun. Sure, reading is nice, but after Month 1, our desire to sit around and read books for days on end is going to drop off pretty quickly. We're more likely going to get through our Netflix queue than our Audible one, and even then we're going to be super bored.

"I'm going to get totally shredded!"

We think the only reason we don't look like a cover model is that our stupid startup is taking up all of our time. When we have tons of time, we're going to hang out at the gym and get into all kinds of activities. Running in the morning, yoga at lunch, then maybe some tennis to wrap the day?

Have you ever done all of those things in a single day? How about the day after that or the day after that? They are straight-up exhausting. There's a reason we're all wearing shirts one size bigger - we're not that motivated to work out all the time. Do we really think that Peloton bike is collecting dust because we just never had the 30 minutes to commit? Because we're all caught up on every episode of Game of Thrones, so…

"I'm going to vacation everywhere!"

Ah yes, we're going to bounce from beach to beach dipping our fat toes into every crystal clear puddle of water we can find. It'll be like the best vacation we've ever had, only it will never end.

Except for the fact that the reason vacation was special was because we weren't always on vacation. After the 5th trip in a row to yet another resort, we start to realize that taking a break only felt so good because we actually needed the break. It's like taking a shower after you've just gotten out of a bath, it doesn't feel "bad", it just doesn't feel refreshing anymore.

"I'm going to finally pick up that one hobby"

With all our newfound free time we're going to learn to play the guitar, master woodworking, and become a gourmet chef - all at once! We're going to the ultimate Renaissance person with all of our newfound interests.

Yet our development of hobbies has way less to do with not having the time than not having the interest to see them through in the first place. Let's not pretend that we were going to be Gordon Ramsay or Jimmy Page just because we have a few extra hours. No one who became great at anything did so because they just had too much free time.

"I'm going to spend tons of time with my family!"

Ah yes, we've neglected our loved ones for so long, now we finally get to make it up to them now that we're retired. We're going to go on lunch dates with our spouse and spend ridiculous amounts of time with our kiddos. We're going to go from being totally invisible to overly present.

But how much of that do they want? Sure, they want us around more, but how much more exactly? As a kid were you thinking "Boy, I wish my Mom would have spent 12 hours a day with me when I was in High School!" No, of course not. Our loved ones most certainly would like more of our time and attention, but they don't necessarily need a hundred hours per month more, and we certainly have it now.

Retirement is not a Transmorgrifier

We all fantasize about how the only reason we're not this idealistic person is that our startups have held us back. We transpose our lack of time with a version of ourselves that automatically would have done all of the right things.

Yet time and time again as more Founders finally pull back the mysterious curtain of early retirement, we find that we're just the same old procrastinating slob we were before our startups - only without a job!

There's nothing wrong with getting the opportunity to retire, so long as we're sober about the fact that retirement only changes the time we have, not the person we are.

In Case You Missed It

What We "Lose" When We Sell Our Startup (podcast) Let’s talk about the emotional toll it takes on Founders when they sell their business, how to spend time when the Startup is gone, losing authority & level of importance, and if there’s a way to prepare to become an ‘exited’ Founder.

What If I Sell Too Early? (podcast) Selling is a tedious process so you shouldn’t just focus on what’s happening during the negotiations but also the pros and cons after the sale is made. And of course, how much you’re being paid for selling is as important as HOW you’re getting paid.

What Are the Most Important Skills a New Founder Needs? Most Founders have a "certain set of skills" that apply to one aspect of their startup. Unfortunately, we sorta need to be a jack of all trades because we're often the only person doing all the work! But what are the most important?