What 5 Retirees Wish They’d Known Before They Retired

​When I set out to interview retirees for this article, I expected the story to be about money.

That’s the assumption most people carry into retirement conversations. Did you save enough? Is your withdrawal strategy right? What does Social Security look like? Those are important questions, and every one of the people I sat down with had done the work on them.

But the money is not what they wanted to talk about.

I sat down with five households of retirees, all in different fields, all at different stages of the transition:

• Frank, a career commercial airline pilot who retired earlier than planned after a cancer diagnosis
• Robert, whose career unfolded across several distinct chapters spanning military service, business, and public service
• Ellen & Greg, a former teacher and a former technology executive who retired within a couple of years of each other
• Ben & Kate, both retired earlier than expected through voluntary buyout programs after long careers in banking and tech
• Craig & Jill, a personal perspective from our own journey which I’ll share at the end

The money was the easier part. What every one of them said, in their own words, was that no one warned them about the transition itself: the identity shift, the empty schedule, and the work of finding what fills the space work used to occupy.

If you’re one to three years out from retirement, this is what these retirees wish someone had told them.

The transition takes longer than you think

Robert: the year with no commitments. Robert and his his wife made an agreement before his last day…no commitments for a full year. That created space to let the next chapter emerge more naturally. “Being able to stop the prior life and be open to a new life,” he said. “God, what do you have for me now? That ended up being really important and wonderful.”

Ben & Kate: decompression mode. Kate’s word for what she needed after nearly three decades in tech. She stepped out and consciously chose not to plan the next thing. “I’m in vacation mode. Ben keeps asking what I’m going to do, and I say, I’ll figure it out when I get there.”

Ellen: it can be years. Her advice to a soon-to-be retiree was to cut yourself slack. “There is a transition period, and you don’t have to have it all figured out. It can be years, three or four or five.”

Give the transition more room than you think you’ll need.

You’ll fill the time

Greg: whatever you do, you fill the time. Greg’s line was the sharpest. During his career, he ran on optimization, dense hours, and high output. In retirement, he watched himself expand the same tasks to fit the day. His response was to get intentional about what he actually wanted to make room for. “You still need to be super intentional. Even in retirement, your life could just be driven along by the activities of the day.”

Ben: five weeks on the road. He assumed retirement would feel leisurely. Then he looked up and realized he had been traveling for five consecutive weeks. “Somehow it’s just busier than I recall during my working time. And I’m holding the pen on the calendar.”

Frank: the routine that wasn’t routine. He had a career built on a shifting-but-familiar rhythm. When it disappeared, he had to rebuild structure from scratch. Gym on Mondays. Swim on Wednesdays and Fridays. Small anchors that kept the days from disappearing.

Your identity has to come from somewhere else

Robert: we are not what we do. Robert made this point more directly than anyone else in the conversations. He watched his accomplishments fade quickly after he left each role. Organizations he had led moved on faster than he expected. Things he cared deeply about were undone by the people who came next. “The things that you do disappear. The people you touch during that, the relationships you build, are the things that are important and last.”

Frank: a career, not a calling. Frank enjoyed flying and made a life out of it, but his identity was never tied to the cockpit. When peers who lived and breathed the airline struggled after retiring, he moved through the transition more easily.

Kate: graduation, not retirement. She refused the word retirement for herself. She called it “graduating” from her tech career. Naming it that way changed how she carried it…something completed, not something ended.

Money looks different when you’re not earning it

Ben: the three buckets. Ben spent 20 years in banking and still thought of himself as an amateur when it came to personal finance. In a planning meeting, our advising team drew three buckets on a whiteboard: safety, income, growth. Something clicked. “That picture helped me see how the machine will pay us and replace the paycheck. I hadn’t visualized it or really understood how it works until we had that conversation.”

Frank: a diagnosis that reframed money. A cancer diagnosis two years before his mandatory retirement changed the money conversation entirely. Accumulation dropped off the priority list. Family security and generosity moved up. The cost to work with an advisor, which had felt optional before, suddenly became worth it. His wife had one number to call, and he had space to focus on cancer treatment.

Ellen & Greg: a bridge income by design. Our team helped them incorporate a Charitable Remainder Trust that pays a baseline income until Social Security and other accounts kick in. It removed the daily worry about where the next paycheck was going to come from. And once the baseline was solid, they could think about bigger things: travel, generosity, supporting missionary friends.

For several of them, faith also shaped how they thought about money, not as a scorecard but as an instrument for family and giving.

If you’re one to three years out

Based on what these households would tell their younger selves:

• Plan for the mental transition, not just the financial one. Every one of them said this in some form.
• Build in decompression time, and don’t rush to fill it. Especially don’t say yes to the first opportunity that comes calling.
• Be intentional about who you’ll spend time with. Greg’s language for this was “orbits” that have to be actively aligned.
• Have a why for what’s next, but let it take shape slowly. Robert’s year without commitments made room for the right yeses.
• Find a peer a year or two ahead of you. Ben and Kate leaned on neighbors who had just been through the same shift.
• Bring an advisor in early, especially as a third voice for couples. The financial planner often ends up being the neutral party who helps two spouses talk about what they actually want.

A personal note

I’ve spent most of this article summarizing the lessons learned from the families I interviewed. Now, I’d like to add my own experience and what I’ve taken away from this season of life.

I retired for the first time at fifty. I hadn’t planned to. I loved what I was doing in financial services, and I wasn’t ready to be done. I honestly don’t even like the word retirement, which is something Kate and I agree on.

What I got wrong at fifty was rushing into the next thing. I said yes to an early opportunity that wasn’t the right fit, and it cost me some time before I found the space that worked. What I got right was keeping a piece of my identity outside my day job before I stopped. I was coaching a college tennis team on the side, and I kept doing that through the transition. It kept me around people I cared about, and I already knew what to say when someone asked me what I did.

The years that followed were full. Jill and I spent a month at a time volunteering at a Young Life camp for ten years in a row. There was more space for my kids, and time to be present when the grandkids started arriving. More time for us as a couple. And around the age of 60, I un-retired. I came back to work at Alterra doing something I love. Three of the people I interviewed used the phrase “flunking retirement” about themselves. I’ll happily add my name to that list. The first article I wrote when I joined Alterra, 4 Parts to a Joy-filled Retirement, is a good follow on to this one.

One last thing from Jill, and I’ll give her the closing word. She pointed out that meeting with a financial planner right when I first stopped was one of the most important things we did. Less because of the numbers, and more because it gave us a shared, external voice in a conversation that otherwise sits mostly with the person who has done it as a career. That’s the piece I would most want a soon-to-be retiree to hear.

A last thought

These folks didn’t retire from something. They graduated to something else, and that graduation took longer to figure out than the finances did.

If you’re on the runway to your own transition, this is exactly the work we love walking alongside people through. The decisions you make now, financial and otherwise, will shape what your first chapter on the other side actually feels like.

Would you like to talk it through together? Let us know. We’d be glad to start the conversation.