My morning routine includes reading ‘The Daily Stoic’ by Ryan Holiday and Stephen Hanselman. The October 25th entry is titled ‘Two Tasks.’ The passage addresses when Epictetus was asked; “what truly makes a person free?” It’s not wealth. Not high office. Not status. It is the knowledge of how to live.
The authors focus upon two essential tasks in Life: be a good person, -and- pursue the occupation You love. Everything else, they say; “ is a waste of energy and a squandering of our potential.” Their advice is simple: say no to distractions, to destructive emotions and to outside pressure, and keep asking, ‘What is it that only I can do?’
As I read it, I realized these two tasks are at the heart of everything I have been writing about in my Encore Phase. A retirement needs a plan for money, and as importantly, it also needs a plan for relationships, identity, health and purpose.
Task One: Be a Good Person…and Keep Good People Close
Being a good person is something we practice with other people, and work quietly supplies most of them. A job hands us daily contact, shared purpose and an identity reflected back by colleagues, without our scheduling a thing. When the job ends, our relationships can disappear overnight. Most workplace friendships are built on convenience, not on a reason to pick up the phone.
The feelings that follow catch many people off guard. Nearly 70 percent of retirees report some emotional challenges early on. The honeymoon fades, the calendar empties, and suddenly You and your spouse or partner are together all day. In the Health and Retirement Study, they reported unhappiness in retirement more than a decline in wealth or even health. A few thoughts to consider:
- Build your social world on purpose. Join something with a recurring structure, such as a class, club or volunteer team, so the same faces show up on a schedule.
- Invest in friendships that don’t depend on the office. Start years ahead, and build across generations so your circle doesn’t shrink with age.
- Talk to your partner. Discuss time together and time apart before the last day, not after.
- Ask a better question. Not only ‘Do I have enough saved,’ but ‘Who will I still see every week, and why?’
Task Two: Pursue the Work You Love
The second task doesn’t expire at retirement. It simply changes form. Retirement was a short period of time in our Life. Today a healthy 65-year-old has a real chance of living into their 90s, and someone who retires at 55 or 60 could spend 35 to 45 years on the other side of work. That is no longer an epilogue. It’s a second adulthood, -and- it needs something worth waking up for.
- Build an identity that isn’t your title. When the label disappears, who are You? Let the answer be bigger than a job.
- Replace the functions of work, not just the hours. Structure, challenge, contribution and belonging each need a new home.
- Name your purpose in advance. ‘More free time’ isn’t a purpose. Service, learning, mentoring and creativity are.
- Protect your body. Drawing on the book, Younger Next Year, I shared that exercise, diet and connection tell our body to grow instead of decay.
- Consider a gradual exit. Part-time work, consulting or a ‘trial retirement’ can ease the transition.
“Freedom isn’t simply the absence of obligation. It’s the presence of purpose.”
Say No to the Distractions
When reading ‘The Daily Stoic,’ (or any books on the Stoics), they offer a remedy for a scattered Life is to say no. In retirement the distractions look different: a day that fills itself with whatever is easiest, or the belief that the last day of work is the finish line . Now well into my fifth year of the Encore Phase, I have come to believe that the last day of work is the least important part of the story. It is simply the doorway.
A few ways to say no with intention:
- Plan in phases, not as one block. A 40-year retirement isn’t one lifestyle. Plan the first stage well and stay flexible about the rest.
- No deadline is not the same as no direction. An unmeasured Life is beautiful, and it still takes deliberate effort.
- Keep it simple. Clear the emotional and physical clutter to make room for what matters.
- Revisit the plan every few years. Your goals at 60 won’t be your goals at 80.
- Give yourself grace. You are not behind, and You are not finished. You are ‘in process.’
Plan for Both
Money gives You the freedom to retire. It doesn’t tell You who to be once You have it. So fund the years -and- also decide how You will be a good person, and what You will do that only You can do.
So, continue looking forward to your Encore Phase with enthusiasm. Take care of yourself, make the most of every day, and always remember;
“Never quit searching. Never settle. Never give up seeking your purpose.”

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