A Career Off-Boarding Checklist

Preparing for life in retirement beyond the financial side is starting to get attention. Imagine that! For example, a recent Wall Street Journal article recommended a more innovative approach to employee benefits to focus on different career stages, including preparing for post-career life. Last summer, a wellness executive friend and I discussed developing programs for his firm to expand retirement planning to the intangibles. It all seems like a dream come true.

Or perhaps it’s just the natural change that comes with life marching on. Admittedly, it’s hard for me to imagine that it was six years ago that I began my retirement with a pot of coffee, an open calendar, and a world of possibilities. Other than financial advice, I was on my own for all the rest — and I learned quickly there’s a lot more to it.

If you’re considering or readying now for retirement, you might wonder, “How hard can planning retirement life be?” I know, I’ve been there too. But turns out even retirement isn’t always what you expect. And it’s not just me saying it.

I keep my toe in the retirement coaches’ world, and at the last annual conference, I learned about some recent surveys that validated what I’ve learned anecdotally — that retirement isn’t as effortless as we might expect. In the Retirement Perspectives and Attitudes Survey conducted by a retirement coach and a blogger/ influencer (and a role model!), only 51% of retirees thought that the transition was smooth, compared to 70% of pre-retirees who expected it would go smoothly.  That was no surprise to me — before retiring, I thought deciding would be the only tricky part. But even tougher was finding ways not only to fill my time but also fill it in ways that would satisfy needs I never thought about — for meaning, esteem, achievement, engagement, significance, and even how I saw myself.

I’m not usually one to give advice; after all, people are different with different needs. But there isn’t much out there to help answer the overwhelming but essential question, “How do you want to spend your time?”

You might have that answer. But if you’re like me, you’ll wonder what questions you must ask yourself to determine how to answer that fundamental question. So, to be a straightforward voice of retirement experience combined with a blast from my organizational past, here’s my “career off-boarding checklist.”

1. There are many different reasons to retire. What’s yours? Time can be a gain in retirement, but it can become a curse if you have no reason to be here other than thinking you’re supposed to or have reached a certain age. Whether initially your decision or not, knowing why your time matters to you will help you establish priorities and give you focus. You’ll find it easier to make choices, take steps, and stay on track.

There’s a world of possibilities out there that, while exciting, can be overwhelming without some forethought. For example, do you want to contribute to your prior work field but on a new or reduced basis? Expand yourself into entirely new interests? Meet new people? Take better care of yourself? Your family? Care for others, your community, or a cause? Learn new things? Travel the world or just take a break? Or maybe all of these. As for me, I retired to try new pursuits before it was too late. Keeping that in mind has helped me make choices and move forward.

The life you want won’t just happen, so think about what matters (or doesn’t) and make it personal and important. Time is a finite commodity.

2. Who am I? I know this may seem woo-woo, but surprisingly, this question required a lot of time and reflection after being directed by work priorities for many years. Sure, I knew the answer wasn’t just what job or other roles I’d held, but what really makes me tick? I thought about what motivates and drives me, what matters to me most, what abilities come naturally, what I can contribute, what I want to learn, what I’ve put off. And that was a good start. Understanding who you are will help you understand what kind of retirement life will be satisfying for you.

3. How do I go forward? I had to manage myself more thoughtfully than when I was working when the objective was clear, and I knew what I had to get done. Some retirement specifics:

a) get serious about time management and maintain a regular structure to your day — you’ll still have downtime (I save mine for evenings and weekends). Still, I needed to maintain a weekday mindset and structure to effectively manage my time.

b) set goals, small goals (e.g., I want to write at least three paragraphs today, get in a long walk, research that course) and bigger ones (e.g., learn to ride a bike (yes, I’m serious); find a volunteer effort that incorporates the holiday spirit and my interests in food and nutrition (suggestions welcome!)).

c) consider your “purpose” — OK, you knew this was coming. I know the “purpose” word can get overused and sound lofty, but I don’t necessarily mean saving the world. I mean your aim, what drives you now, your direction –what expresses who you are, and the ‘ole gets you out of bed in the morning. Me? I want to continue to grow and share a camaraderie with others by writing about my retirement experiences.

d) redefine “work” — I’m using “work” now to mean more than employment — it’s about how you’d like to do what you’d like to do (whether paid or unpaid) through new interests, service, artistic work, learning, etc.

4. Stay curious. I wasn’t a font of imagination when I needed most to generate ideas, so I looked for inspiration — everywhere. I read a lot and researched leads that sparked my interest. (Tip: many retirement coaches have newsletters that curate the best articles and resources.)

5. Stay positive. I don’t mean the “only positive vibes” stuff because life’s not always upbeat, but a positive, growth-oriented approach is essential to moving forward. (Some days, you’ll really need this reminder.) It’s a process of trial and error but finding out what doesn’t work is also valuable information.

6. Keep leisure at leisure time. Contrary to retirement stereotypes, relaxation is not how I want to spend my entire time. While to each their own, I think leisure is essential but best left to its allocated section of your life.

7. Don’t overreact to boredom. One of the biggest fears people have before retiring is being bored. I’m not talking here about relaxation and quiet time, but times when you’re itching to do something meaningful but don’t know what that is. Even with the best of intentions and plans, unwanted idle time can happen for some of us.

Downtime is part of the process of building a life after retiring. But for some of us, it’s very uncomfortable. I’ve found that it was best for me to accept it when it happens, remember it’s part of the process, and not overreact with a lot of negative feelings (I can get frustrated, tense, agitated, panicked, embarrassed, you name it). Sometimes I just change things up — I get up and move to not give in to those additional emotions. It then becomes much easier to make my way to outlets that are meaningful for me. Boredom has a great benefit — it’s leading you somewhere else. Trying new interests, whether they stick or not, is both satisfying and rewarding for me, someone who likes to feel a sense of achievement — and often shows me where other interests and skills lie.

8. Maintain/develop your social network. Making new friends won’t be as easy as when you worked, but it’s always worth the effort to find and seize opportunities to get to know new people, even if they don’t fall into that exceptional BFF category.

9. Enjoy the Ride. Looking back on six years of retirement, I asked myself whether I’d accomplished what I set out to do. I wanted to slow down <check> and uncover new interests — there, I’ve only scratched the surface. Of course, I’m not done yet. And I’ve realized that I can spend too much time on the outside looking in — by expecting, criticizing, comparing — ironically, all because I don’t want to waste time. It’s funny how it can come to you that there’s a delicate balance between wasting time and valuing it — all of it.

I hope that my attempt at a retirement planning checklist will help you exit your career as successfully as you started it.