You’ve retired — or you’re planning to soon. It’s exciting… until it’s not. What comes next? Retired CFO Lisa Haynes shares three lessons she learned from navigating this life transition.
By Lisa Haynes
You’ve retired — or you’re planning to soon. It’s an exciting phase of life. It’s wonderful… until it’s not. What will you do for the next 20+ years of your life?
Retiring — whether by choice or not — is a major life transition. The Holmes and Rahe Stress Scale ranks it as the 10th most stressful life event, ahead of things like becoming a parent or taking on a mortgage. And yet, those events are planned down to the last detail.
Retirement is usually well-planned financially. But when it comes to the emotional and psychological side of things, many people just wing it — and end up struggling through what should be a fulfilling chapter of life.
Your financial advisor may have helped you prepare for life without a paycheck, but here are three things they likely didn’t mention.
We live in a society where ‘What do you do?’ is a standard question. For many, identity is tied to their title or career. You might think this doesn’t apply to you — maybe you weren’t ‘married’ to your job. But work is more than a paycheck; it’s a source of identity, pride, and belonging.
‘I’m retired’ can feel like a step down from CEO, SVP, or VP. Retirement often brings an unexpected void when that professional identity fades — and grief can quietly creep in. A psychological shift has to occur.
Retirement is not just about leaving your job; it’s about redefining who you are after. It’s about rediscovering the passions and interests that took a back seat to work. I call this the “from what→ to what” transition – it’s not just about what you’re leaving, but what you’re stepping into.
Two simple but powerful exercises I guide clients through:
Craft an introduction that paints a new vision of what retirement can look like — for yourself and for others.
For years, your life ran on structure — guided by calendars, deadlines, and meetings. Even if you had flexibility, your time was still framed by work demands.
When you retire, that structure disappears. And while that can feel exhilarating at first, the honeymoon phase eventually ends. For many, the unstructured time can be disorienting and even demotivating. Without the routine, goals, and deadlines, accomplished people can feel adrift. The dark side of retirement includes high instances of depression.
When I retired, it was an exciting moment. I went through all the feelings and some of the grief, but quickly realized that the way I’m wired, structure matters. I needed to feel like this was not the end, but the beginning of something.
One day, I used the phrase, “I’m Killin’ It” as it relates to retirement, and that became my plan. I used the phrase as the foundation for eight essential elements to a fulfilling retirement. For example, the “K” stands for Keep Moving — that’s physically, mentally and socially. If we’re not careful, retirement can land us in a comfy recliner, binge-watching Netflix, and scrolling social media.
Moving is the best defense against the dark side of retirement.
When your lifestyle changes, your relationships shift — sometimes in unexpected ways. Daily connections you once had at work begin to fade. That monthly lunch with colleagues becomes quarterly… then maybe once a year.
It’s not just former coworkers. Relationships with friends, partners, and even adult children can change. And if you’re not intentional, you might become the go-to for errands or favors because you’re retired and have free time.
The key is that you must be intentional about who is in your circle and the boundaries you set for those relationships. It’s worth pausing to reassess your relationships. That sounds extreme, but it’s worth asking: Which relationships still matter? And what kind of connections will support your emotional, social, and psychological well-being in the future?
Now, you get to choose who’s in your circle — and that choice is more important than ever.
These three issues — identity, structure, and relationships — often catch retirees off guard. With a little foresight, these challenges can become the building blocks of your most meaningful chapter yet.
Lisa Haynes traded the C-Suite for a life she loves—and now helps others do the same. A retired CFO turned Retirement Coach, speaker, and author of Retired and Killin’ It, Lisa shows professionals how to reinvent themselves, find purpose, and make their next chapter their best. Her signature Killin’ It formula turns “What’s next?” into “I’m thriving.” Learn more at www.killinitretirement.com.
