Why I Need a Retirement Mentor

Three-plus decades ago, friend and fellow writer Cathy Madison told me something that has stuck with me ever since: that when you’re self-employed, which I have been since my mid-20s, you never really retire, you just wake up one day and realize all of your clients are gone.

That day hasn’t yet come, but I can see it beginning to dawn. Fewer clients, smaller projects. But I’m not complaining. In fact, I’m largely to blame as I now only say yes to projects I can do from anywhere at any time, without having to schedule calls, log on to online meetings or drive across town for in-person ones. 

Several years back, on the advice of a few older colleagues , I decided to test drive my retirement. I spent one Minnesota winter in Panama. I lived with my sister Diane and her family another winter. And one spring I enjoyed six weeks in Paris courtesy of a friend who loaned me her Latin Quarter apartment.

I also found a few retirement mentors. They, of course, include my fellow Word Sisters, all of whom were a bit ahead of me in embracing retirement. They also include Joe Casey, host of the Retirement Wisdom podcast. Not only did I learn a lot from him and his guests, he hired me to write for his blog, giving me the motivation (and a bit of income) to learn more about retirement—the pros and cons, the ups and downs—than I might have had my own.  

Here are a handful of things I’ve learned that might be helpful to you:

• Retirement is not a one-size-fits-all journey. Some want relaxed days without a schedule while others are actively working through a bucket list.

• Money matters, but not always as much as you might think. How much money you have can bolster or constrain the size of that journey. What matters more are your own personal tastes, hopes and dreams.

• Accountability counts. One of the biggest challenges I and many of my fellow retirees face is staying disciplined. Why do today what we can put off until tomorrow? But I’ve learned the hard way that while leaving things until tomorrow may feel good today, there will eventually be a price to pay. Checking in regularly with friends and family can help. So can having a mentor or goal buddy.

• Your health: here today, gone tomorrow. Although both my parents died when they were 70—my dad a year after a lung cancer diagnosis, my mom in an instant due to a heart attack—I always thought I’d grow old like my grandmother and die in my sleep some years after celebrating my 90^th  birthday. However, since turning 65, I’ve experienced a number of health issues, all minor thankfully, but they’ve made me realize I’m just a diagnosis away from something more serious. So now is the time to make the most of my time.   

• Staying socially active really does matter. After being unplugged since the start of COVID, I have begun reconnecting with friends in person. A visit with a friend at her house two months ago led to having dinner in a restaurant with another friend, and this eve I’m meeting a third friend for a work-related reception followed by a movie.

Retirement is a significant life transition that requires careful planning and consideration. While it can be tempting to go it alone, having a retirement mentor (or several!) can provide numerous benefits. From personalized guidance and experience-based insights to accountability, emotional support and help avoiding common pitfalls, my mentors have become trusted companions on my retirement journey, one my future self will thank me for.

When Will I Do It?

My friend Maery did it after fracturing her shoulder at a company outing.

My cousin Eugene did it when he ran out of staples for his office stapler.

My sister Karen did it when COVID-19 closed the dental office where she worked.

What did they do?

They retired.

But unlike me, they all had employers to retire from. They also all had a key moment when they knew it was time to do just that.

But as a freelance writer who works for dozens of clients, there’s no one employer to retire from and since I haven’t yet had a “now’s the right time” moment, I’m still saying yes to most client work that comes my way. Thankfully, I enjoy the work…and the people I work for.

That said, I am beginning to think more seriously about retirement and what it might look like for me.

Despite the fact that I’ve been dreaming about (and saving for it) since I was 22, I don’t have a very clear picture. That’s one reason why, when I turned 60 three years ago, rather than celebrating with a big party, a piece of jewelry or an exotic trip, I took a one-year sabbatical.

Though I missed having work as a way of structuring my days, I really enjoyed the downtime and the chance to unplug both personally and professionally. I also enjoyed the chance to travel for months at a time.

Although I’ve since returned to freelancing, I now say yes only to projects I can do from anywhere at any time. That way, I still have plenty of flexibility and free time, a lot of which I just putter away. Most days that feels like exactly the right thing to do.

Other days, I’m more engaged. I’ve also started journaling again and gotten reacquainted with art supplies I haven’t touched in years. I’m cooking some and reading more. I’m writing letters and calling friends. I’m even enjoying routine household chores, plus getting estimates for several home improvement projects.

Increasingly, it’s these things—not my client work—that’s giving structure to my days…and no doubt moving me closer to retirement. What sign will tell me that it’s finally time? I don’t yet know, but I do look forward to finding out.

Slouching Toward Retirement

I’m not ready to retire yet.  But if I squint I can see it from here. And I don’t like how it looks.

 Baby Boomer To Do List

1. Figure out a retirement that I want to be a part of.

2. Invent a new approach to assisted living/aging in place.

3. Think up better ways to volunteer/give back.

4. Consider my legacy—what it is and how I can help others understand and value it.

5. Resist irrelevancy, crankiness, and being set in my ways.

1. Figure out a retirement that I want to be a part of. 

Trend specialists are always predicting that Baby Boomers will change the face of retirement, just as we have changed so many other institutions (the workplace, motherhood, marriage, etc.)  I sure hope so. Living in a retirement community where golf and bingo are the main attractions does not appeal to me.

Boomers tend to think we’re pretty interesting, and we assume we’ll remain so in retirement. In fact, being cool is probably our birthright! Of course, we’ll invent a better version of retirement.

But I wonder how excited we’ll be about riding our Harleys across the country, when our backs ache and our knees are going . . . . And that assumes we’ll even be retiring. Financial necessity will motivate a lot of Boomers to keep working past age 65. And who will be taking care of our elderly parents and the kids that might not be fully launched?

OK, OK. That’s WAY too much reality. Retirement is years away. Let me get back to creatively daydreaming about how I want retirement to look.

I want it to look like less work, more fun. I want a smaller place (less cleaning, less stuff), but I still want to have a postage stamp-sized yard so I can garden on a smaller scale. I hope to resume some hobbies I set aside for lack of time – pottery, for example. I’d like to learn how to do raku. Making stuff from paper—cards, collages and so forth. Jewelry and stained glass. Quilting and sewing. Maybe I’ll take up canning. Indulge my foodie self a bit more. Start a gourmet dinner group.

Travel. Maybe I can learn enough Italian so I could teach English in Italy while my husband learns the secrets of Italian cooking. Or perhaps I can study abroad (can grown-ups do that, too?), Sounds expensive. Wait, wait. No reality.  I’m daydreaming here.

Be more random and spontaneous. Take back roads and visit antique stores and cafes in little towns instead of always taking the interstate. Go to movies, concerts, plays, art galleries that I’ve never heard of. Decide on a Thursday to visit an airline fare sale city on Saturday—just to see what’s there.

I’ll definitely keep on writing whether or not I get paid. I’ve got a lot more stories to tell and perspectives to share. Besides, I’m a writer to the bone—I can’t stop even if I want to.

Keep thinking and learning. I’ve never understood how you retire your mind.  I’m way too curious and I love learning new things. I hope to audit college classes, take workshops, and read voraciously.

I intend to continue volunteering, but perhaps in different ways (more to come about #3).

I plan to keep active and healthy, but I don’t want to be obsessed with it. I’m unlikely to spend more than an hour per day on keeping fit.

I want to help my kids fix up their homes when they buy them and play with their kids if they have some.

Oh yeah, I’m still hoping to have some lasting impact on the world. I figure I’ve got at least 20 more good years. I ought to be able to change the world in that amount of time, right? I know, I know. Tick tock.

Well, except for the last one, these are pretty modest retirement goals. Sounds like a life I could live.

What do you hope to be doing?