Last weekend, I flew to Montana for a short annual retreat with a group of old friends.

During the retreat, I had a long conversation with one of them on the topic of retirement. This friend is very financially successful by all objective measures, but often laments his lack of time and freedom.

His plan: To push hard the next ~10 years to hit a number, at which point he will retire and begin spending more time with his young kids (who will be in their early teens by then) and pursuing various hobbies.

It's a common plan—grounded in delayed gratification—that we defer happiness to some future (in this case, retirement). In most cases, that future is glamorized in our minds as an idyllic land of free time, health, prosperity, loving relationships, and freedom.

The problem: What if that future is something of a mirage?

What if, as we, the famished voyager, approach, it slowly melts away and reappears further out on the horizon? What if we reach the idyllic land and find it strikingly less idyllic than we had envisioned?

In today's piece, let's discuss the perils of deferred happiness, the retirement trap, and the beauty of the designed life.

The Perils of Deferred Happiness

The Wall Street Journal recently released a visual breaking down how people spend their time in retirement.

The visual shows that the majority of a retiree's time is spent on sleeping (9 hours), relaxing and leisure (6 hours), and watching television (4.5 hours). Very little time is spent on reading (0.5 hours), socializing (0.5 hours), or exercise/recreation (0.3 hours).

Most of us create this beautiful image of what retirement will look like, but the reality is (likely) much different.

Why? Well, the image we create is based on who we are today, while the reality will be based on who we are at retirement age. Today's you has loads of energy, physical vitality, and a long list of healthy friendships, but a future you may not.

My friend Khe Hy once wrote about the all-too-common "when, then" syntax that says, "When I get [X], then I'll be happy."

In my view, it's not a rebuke of delayed gratification, but of (1) deferring ALL happiness to some future date and (2) believing that some external achievement or reward will drive lasting happiness.

For example, I reached 1 million followers on Twitter a few days ago.

The satisfaction from hitting the milestone lasted about an hour. The happiness boost dissipated and I was back at a baseline. If I had spent the last three years writing on Twitter thinking I would feel great when I hit this mark, I would have been seriously disappointed.

The lesson is that we can never make the mistake of thinking that an external achievement will create lasting happiness.

It's a trap.

Retirement is the most common version of this trap: We say we'll be happy and do all of the things we've wanted to do...when we retire.

But as the WSJ visual so clearly shows, the idyllic vision in our mind may not be quite as fantastic in reality.

Reframing Retirement: Incremental Design

My proposed solution: We need to reframe retirement.

The traditional concept of retirement is grounded in a foundational assumption that there should be a "before and after" within your life—that you grind away for years and years in the before and then get to enjoy the after.

I believe this foundational assumption is broken.

There needn't be a before and after within your life—it can all be fluid, a during.

The goal is to design a life that you don't need to retire from.

A life that has the freedom to balance fulfilling work with the relationships, hobbies, experiences, and pursuits through which you derive joy.

But I'm not going to tell you that this is easy (or that I can sell you the solution in some internet course for 4 easy payments of $29.99).

What I am going to tell you is that it is possible—particularly if you have an awareness of the goal and build toward it incrementally.

The traditional arc looks like this:

• 20: Start work
• 20-65: Work 40-60 hours per week
• 65+: Retire and enjoy life

The designed life arc might look like this:

• 20s: Start work, hustle to build a solid foundation
• 30s: Identify and focus on highest leverage opportunities
• 40s: Eliminate or delegate to increase freedom
• 50s: Identify most meaningful work
• 60s+: Focus on most meaningful work

The idea here is that there isn't a before and after, but a steady, incremental line of growth and progress that leads to more freedom and fulfillment over time.

The designed life arc doesn't require you to defer happiness to some future date, as you will derive it along the way with continuous growth and improvement.

It doesn't matter where you are today—whether you're young or old—there's no such thing as "falling behind" on a path based on continuous improvement.

Wherever you are, you just need to make one good decision, one tiny incremental improvement, and go from there.

The Designed Life

My friend Jacob Turner recently told me about an experience he had on a flight home from vacation with his wife. The flight attendants announced a "return to reality" after landing, which induced a number of groans from the passengers.

But as Jacob reflected on the moment, he realized he was excited to be back to his reality.

"Reality can be pretty great," he said.

Especially if you design it to be.

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