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Plan for the money and you can still end up with nothing to do on Tuesday.
That is the part of retirement that hits founders late. We spend decades with a calendar so full it feels like a personality. Then the calendar clears, and the question is not "can I afford this?" but "what is this for?"
How much free time will you actually have?
More than you expect. In the 2024 American Time Use Survey, people 65 to 74 spent 6.52 hours a day on leisure and sports, and people 75 and over spent 7.56 hours, the most of any age group.1
Seven hours is not a vacation. Seven hours every day is a shape you have to fill, and for someone who spent years building a company, leaving it unshaped is a risk I would not take lightly.
Why does purpose matter more than the hobby itself?
Because the hobby is the container and purpose is what goes in it. I want to be careful here, because this is the kind of topic where blogs overclaim.
In a 2019 study published in JAMA Network Open, researchers followed 6,985 U.S. adults over age 50. People in the lowest life purpose category had a hazard ratio of 2.43 for all-cause mortality compared with those in the highest category.2 That is an association in an observational study. It does not prove that finding purpose adds years, and the authors note limits such as the possibility that illness lowers purpose in the first place.
What I take from it is modest and useful: it is reasonable to treat purpose as part of a retirement plan, not a decoration on top of it.
The loneliness risk
The National Institute on Aging says research has linked social isolation and loneliness to higher risks of high blood pressure, heart disease, a weakened immune system, anxiety, depression, cognitive decline and even death. It also lists retirement among the changes that can leave people unexpectedly alone.3 A founder who sees five people a day through work can wake up to zero without noticing the cliff coming.
What turns a hobby into purpose?
Three tests. I use them on my own plans, and they work on most things.
| A pastime | A purpose |
|---|---|
| Fills the day | Gives the day a reason |
| You do it alone, on your schedule | Someone is counting on you, on a rhythm |
| Stays at your current level | Keeps stretching you |
| Ends when you get bored | Survives a bad week |
It serves someone
Teaching, coaching, mentoring, volunteering and building things for others all pass this test. The reason is simple: a commitment to another person is the strongest alarm clock there is.
It has a rhythm
A weekly class, a Saturday build day, a monthly board meeting. Rhythm beats motivation. My own life is built on that principle, which I wrote about in discipline is freedom.
It keeps stretching you
If you are already the best in the room at your retirement hobby, find a harder room. Skill growth is the reward that never expires.
What can founders do with the skills they already have?
You have unusual assets for later life: judgment about people, practice at making decisions with incomplete data, and a habit of building. Aim them somewhere new instead of repeating the old job at half speed.
Some directions that use those skills, with no promises about any of them:
- Mentoring younger operators, free or through a program you respect.
- Teaching a subject you know to adults who want to learn.
- Serving on a board or advisory group for a nonprofit or school.
- Building something small and physical. Woodworking, gardening, restoring something old. Making things you can touch is a relief after a career of screens.
- Learning something hard on purpose. A language, an instrument, a trade.
- Community service with a team and a schedule.
None of that requires a business plan, and that is a feature.
What if the hobby starts earning money?
It happens to founders more than most. Treat it with a little care, because the rules are specific.
The IRS says that if someone receives income from an activity carried on with no intention of making a profit, they must report that income on their tax return. It also lists factors that help decide whether an activity is a hobby or a business, including whether it is run in a businesslike way, how much time and effort goes in, whether you depend on the income, and whether it turns a profit in some years. No one factor decides it.4
My advice is to decide on purpose which one you want. If the hobby is a gift to yourself, keep it a hobby and report any income. If it is becoming a business, treat it like one, with records and a plan, and ask a tax professional. Do not let a hobby quietly turn into another job that owns you.
How do you try a hobby before you retire?
Audition. You would not hire someone without a trial.
- Pick three candidates that pass at least two of the three tests above.
- Try each for ninety days with a real commitment, not a single afternoon.
- Score them on people, rhythm and stretch. Drop the one that scores worst.
- Add a line to your plan. Give the one you keep a small yearly budget for tools, travel and fees.
- Tell someone. Say it out loud to a person who will ask you about it.
Retirement is not a place you arrive. It is a calendar you design before someone else fills it.
My grandmother's question about my plan, which I tell in the original story, was about money. The harder follow-up she never had to ask is the one in this piece. I wrote about rehearsing a perfect Tuesday in retirement lifestyle and hobbies, and this piece goes deeper on purpose. For the bigger picture of how the work, money and rhythm fit together, read retirement lifestyle design for founders.
More guides are in the Investing and Retirement hub.
Educational content, not financial, tax, legal or investment advice. Talk to a licensed professional about your situation.
Keep building.Ekai
Questions people ask
How much free time do older adults have?
In the BLS American Time Use Survey for 2024, people 65 to 74 spent 6.52 hours a day on leisure and sports, and people 75 and over spent 7.56 hours, the most of any age group.
Does having a sense of purpose help health in later life?
A 2019 study of 6,985 U.S. adults over 50 found that people in the lowest life purpose category had a higher risk of death during follow-up than those in the highest. It is an association from an observational study, not proof that purpose causes longer life.
Do I have to report income from a hobby?
Yes. The IRS says that if you receive income from an activity carried on with no intention of making a profit, you must report that income. Whether an activity counts as a hobby or a business depends on several factors, so ask a tax professional.
How is purpose different from a hobby?
A hobby fills time. Purpose gives you a reason to show up that involves other people, a rhythm and a challenge that grows.
Sources
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