RETIRE TO SOMETHING, NOT AWAY FROM SOMETHING

Derek Hagen
Jul 16
4 min read

Hand-drawn stick figure crosses a "Retirement" finish line with question marks overhead; a "Now What?" sign stands to the right

❝The trouble with retirement is you never get a day off.❞ -Abe Lemons

Most people plan their exit. Few people plan what comes next.

I'm sitting across the table from a client who's about to retire. I ask what they're most looking forward to.

Not having to go to work.

I've heard that answer, or a version of it, more times than I can count. People want out of the rat race. People take jobs they hate so they can retire young. People put up with work they don't like so they can save enough to stop doing it.

It feels like an answer. It isn't. "Not having to work" tells me everything about what you're leaving. It tells me nothing about where you're going.

Most people don't know how they'll fill their days.

WORK GAVE YOU MORE THAN A PAYCHECK

Most people know what they're walking away from when they retire. The paycheck, the boring meetings, the colleagues who drain them. What's harder to see is everything work was quietly providing that they never thought to replace.

Hand-drawn wheel divided into five sections: Paycheck, Structure, Direction, Purpose, Social Connection; shows what work provides

Work gave you structure: a reason to get up, a schedule that organized your day. It gave you direction: something to move toward, problems to solve. It gave you purpose: a sense that what you did mattered. It gave you identity: an answer to "what do you do?" It gave you social connection: colleagues, relationships, a community that showed up every day whether you liked them or not.

Hand-drawn radar chart with five axes: Paycheck, Structure, Direction, Purpose, Social Connection; shows work covering all five needs

Whether you loved your job or hated it, it was doing all of those things.

Retirement doesn't just remove the job. It removes the infrastructure.

Hand-drawn iceberg with "Paycheck" above the waterline; Structure, Direction, Purpose, Social Connection, and Identity submerged below; illustrates what retirement removes beyond the obvious

The Value Compass is designed to help you gain insight into your own values and how they guide your thoughts, feelings, and actions. It can be used to explore your personal goals and motivations, as well as to gain a better understanding of others' values and how they may differ from your own.

WHAT RETIRING AWAY LOOKS LIKE

Crossing the retirement finish line feels extraordinary. You trained for it, worked toward it, and the moment of crossing it is everything you imagined.

Then you stop. And if there's nothing on the other side, the finish line turns out to be less of an arrival and more of an ending.

Take social connection. Men typically get most of their meaningful social relationships through work. When that ends, the social network goes with it. Retirement without a plan for connection is lonelier than most people expect.

Take the golf fantasy. You've always wanted to play more golf. Retirement arrives, and you play every day... for a few hours... not seven days a week. The projects around the house get done. The hunting trips happen. Eventually you run out of things that fill the day the way work did.

Seven Saturdays sounds like a dream. The seventh Saturday in a row is something else entirely.

Studies consistently show a significant number of retirees go back to work. It's not because they need the money. It's because work was the one thing providing structure, direction, purpose, identity, and social connection. They didn't know that until it was gone.

Hand-drawn radar chart with five axes; illustrates how retirement collapses most of what work provided

RETIRE TO SOMETHING

Think about the people you know who've retired well. What do they have in common? Now think about the people who haven't. What's the difference?

Most people answer that quickly. The ones who retired well had something to retire to.

It doesn't have to be grandiose. It doesn't have to be a second career or a nonprofit or a passion project. It can be taking care of grandkids, working part-time at your favorite bike shop, or building something you've always wanted to build. But it has to be something; something that puts structure back in the day, gives direction to the week, connects you to other people, and answers the question of what you're actually for now that the job isn't doing that anymore.

Hand-drawn stick figure moving away from red "Work" label toward blue "Life Worth Living"; captioned "Retire TO Something" above and "Not AWAY From Something" below

LIFE COMES BEFORE MONEY

Money is a means, never an end. Yet most retirement planning conversations stay on the exterior: do you have enough, when can you retire, how long will it last, what's your withdrawal rate?

Those are important questions. But they're downstream of the most important one: what is retirement actually for?

A financial plan that gets you to the finish line without asking what's on the other side isn't a complete plan. It's half a plan.

Figure out what you're retiring to. Get the money to follow that.

You get one life; live intentionally.

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