
Try out retirement before you quit. Ten practical steps from Benjamin Brandt's book to build a life you'll actually enjoy living, starting now.
Today wraps up our three-part look at Benjamin Brandt's Retirement Starts Today. The book's central idea is one I have long believed: don't wait until your last day of work to figure out retirement.
Decades of financial planning do nothing to prepare someone for the lifestyle shock. Work supplies structure, routine, social contact, goals, and identity. Once those vanish, some people flourish. Others feel unmoored.
The solution is not to retire early. It is to start building the non-financial parts of retirement years ahead of time. Here are ten practical ways to do that.
1. Simulate a normal week, not a vacation
Take a week off and force yourself to treat it like retirement. Do not fill it with trips, errands, or projects. Live the unscripted days you would actually face. Many people discover they love the freedom. Others find the lack of structure unsettling. Both reactions are useful data.
2. Build serious hobbies before you need them
A lot of people retire with nothing to do but watch television and browse the internet. That is not a sustainable 30-year plan. Start testing interests now. The goal is not to find the perfect hobby. It is to build engagement and curiosity into daily life.
3. Leave time completely unplanned
Most workers have not faced genuinely unscheduled time in decades. Their days are driven by meetings, deadlines, and family obligations. Try blocking out a few hours with nothing on the calendar. Pay attention to how you respond. The reaction tells you a lot about what the first months of retirement might feel like.
4. Strengthen social connections outside work
Work provides a built-in social network. When it disappears, isolation can creep in quickly. Brandt emphasizes this point, and it is hard to argue with. The happiest retirees I know already had strong social rhythms – clubs, volunteer groups, regular meetups – established long before they stopped working.
5. Take a weekday off and live it like retirement
Use a random Tuesday or Wednesday. Sleep in. Walk the dog. Go to the library. Meet a friend for lunch. See what that rhythm feels like. Some people realize they need more stimulation than they assumed. Others find the slower pace exactly right.
6. Build identity outside your job title
Career status, income, and being needed are powerful identity anchors. When they disappear, some retirees feel psychologically untethered. Start cultivating other sources of purpose now. The broader your identity becomes before retirement, the smoother the transition.
7. Aim for five go-to retirement activities
Brandt recommends experimenting until you have at least five things you genuinely enjoy doing. These are your fallback options for ordinary days. They can be simple – reading, walking, cooking, gardening, a weekly game night. Without them, retirement can feel empty fast.
8. Prioritize physical preparation
People obsess over the 401(k) balance and ignore basic fitness. Mobility, endurance, strength, and energy levels determine how much you can actually do in retirement. Start building those habits now. A strong body makes the freedom far more enjoyable.
9. Transition gradually, not abruptly
A slow fade works better than a hard stop. Cutting back hours, taking a sabbatical, or shifting to part-time work gives the mind time to adjust. The book makes this case well, and it matches what I have seen in practice.
10. Learn what genuinely makes you happy on ordinary days
Most people are disconnected from what they actually enjoy when nothing is required of them. The only way to discover that is through experience. Try things. Pay attention. Those lessons will shape a far better retirement – and they often improve the years before retirement too.
Financial preparation is critical. It is not the same thing as retirement preparation. The people who build happy retirements rarely start from scratch on day one. They build their lives little by little, for years ahead of time.
This ends the mini-series. What did you think?
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