Retiring Early is a Broken Concept

"I want to put $50 million in the bank by the time I'm so I can retire early and never have to work again!"

Ah, the common refrain and justification of every startup dreamer, from the Founder across to the earliest employee. If only we could put that magic pot of gold into our coffers, then we could do what we really want to do.

Except it begs the questions:

1. How much of what we really want to do can we already be doing?
2. Do we really not want to work or do we really just want to feel safe?
3. What the eff are we going to do at (whatever age) with nothing to do all day?

Time and time again when I query Founders, beyond the surface level stuff, about how hard they have thought through this lifetime goal that they are sacrificing everything for — there's rarely a detailed answer. And that's a huge problem considering we're often risking everything for that goal.

We don't want to stop working, we want the option to choose

In my experience with seeing hundreds of cashed out Founders, the folks that were so driven at their craft to cash out were the people least comfortable with "never working again". That's often because we're framing the problem the wrong way. We're not saying we don't want to work again, we're saying we want the optionality of how and when we work.

But are we really so leveraged right now? How much of our optionality is coming from our lack of commitment to pursuing our true desires versus letting the world around us determine those outcomes for us? Are we saying that we want a pot of gold to allow us to escape those demons? If so, we have to ask ourselves if "retirement" is what we're after, or if having more agency over our own lives is, and how much money is required to get that.

We want the safety of knowing we'll be OK financially

We all want to feel safe. We want to feel from losing our job, or having some sort of life event, or just the safety to tell someone "fuck you" and know we'll be OK with the aftermath (it's called "Fuck You Money" for a reason). But let's be honest — do we need an ungodly sum to get there?

Play that out. Look at how much we'd need to survive being without a job for a year, or what a crazy catastrophic life event might cost. How much is that really? $250k? A million? It's probably not $50 million unless our life events involve living like Scott Storch or MC Hammer for a year (great stories, btw). The truth is we probably don't need that much money to have the cushion that would make us sleep well at night. And setting ourselves to have to make some made up enormous number is a huge waste of time.

What are we going to do with nothing to do?

Let's also not lose sight of the fact that our jobs, while hellacious at times, also tend to occupy and extract a tremendous amount of our most creative, powerful energy. The kind of energy that makes an incredible change. There are very few things that we can channel that energy into without a job that (I'm including charity as a job) that can have that impact. Let's not downplay how well our jobs bring out the best of us in many ways.

But forget that for a moment. What the hell are we going to do for 16 hours per day for the rest of our lives? Get caught up on books? How many books are you possibly going to read? Spend more time with friends and loved ones? Guess what — they all have shit to do, they haven't been waiting around for us to free up time. The reality is we likely need more time to invest, but not all 16 hours. What we need is a re-allocation of time, not necessarily a wholesale change in our entire life.

So are you saying retirement sucks?

No! I'm saying we don't think it through well enough. We set up insane goals with a fraction of a percentage chance of hitting them (IPO, Sale) and burn our most valuable youth in their pursuit. These aren't small things, and we can't get them back. We need to change our thinking from "retiring early" to "shaping my life the way I want it." And that doesn’t have to wait for an IPO. The most important changes we want can all be made now.

Think about it.

In Case You Missed It

Where to Find Opportunities in a Recession When crisis is unavoidable, strong Founders will seek out the opportunities during a recession.

How do We Tell Our Staff We’re About to Run Out of Money? The key to communicating with our staff about money is to do it early and to get everyone on the same page.

Overwhelmed (podcast) Startups are often portrayed as a go big or go home affair, and as Founders, it's easy to get caught up chasing monumental goals and forget about the daily actions that will actually get us there.