Are You Retiring FROM Something or TO Something?
By Luke Sullivan on October 27, 2026
Recently, I met with two different clients who do not know each other (to my knowledge). And they both remembered something I told them separately –
It’s important to retire to something, not just from something.
It had stuck with them because they were putting it into practice.
One client is traveling across the country with the goal of drinking wine from a local winery in every state. Another is preparing for retirement and considering spending at least a month in Europe while learning Italian.
Their plans are completely different, but both are thinking beyond the date they stop working.
They are thinking about what comes next.
Most people spend years preparing to retire from work. They save, invest, reduce debt, and calculate how much income they will need.
Those things matter, but they only answer one question –
Can I afford to retire?
They do not answer the other question –
What am I retiring to?
Work provides more than a paycheck. It creates structure, relationships, responsibility, and a sense of purpose. When that suddenly disappears, even someone who is financially prepared can begin second-guessing the decision.
Sometimes retirees drive their spouses crazy. Sometimes they develop bad habits. Sometimes they simply feel uneasy because, after spending decades pursuing one mission, they haven’t decided what the next mission will be.
Everyone handles retirement differently, but I believe most people need some form of renewed purpose.
That purpose does not have to be impressive. I have seen clients become restaurant hosts, volunteer at museums, travel the country, learn new skills, and become more involved in raising their grandchildren.
The activity itself is not the point. The point is having somewhere meaningful to direct your time and energy.
I often ask people to picture an ordinary Tuesday at 10:00 a.m. after they retire.
You are not on your first post-retirement vacation. It is not a holiday. Your family members are busy living their own lives.
What are you doing?
If the only answer is, “At least I’m not working,” that may feel good for a while. But relief from your old life is not the same as excitement about your new one.
Ideally, this conversation begins at least 12 months before retirement. You do not need a perfect answer or a completely mapped-out schedule. You should, however, begin brainstorming what the next chapter could look like.
A financial plan can help determine whether you can afford to leave work. It cannot choose your next mission for you.
Don’t just plan what you are retiring from.
Start planning what you are retiring to.
