In the seventh…or maybe ninth…grade, the assignment in English class was to write a philosophy of life. I wish I’d kept it because I have no idea what I ended up with but I remember how difficult it was to write. The problem wasn’t properly putting words together, it was figuring out the proper words. Philosophy of life? Wow. It seemed like a lot. I was just a kid.

From my grown-up perspective, this exercise should begin in the fifth…or even third…grade. Every kid should write an annual philosophy of life, beginning to identify what’s important to them. If I had worked on my philosophy of life a little every year, by the time I graduated from Indiana University, I would’ve had the foundation for a now-to-retirement map. Philosophy of life and life map (or as I’m thinking of it, a map between where I am now and retirement) aren’t exactly the same thing, but the first informs the second. We’re all on a path between wherever we are right now and our retirement. The trick is figuring out how to plot the course deliberately. It’s never a straight path but mine might’ve involved less wandering if I’d spent more time mapping the destinations.

Since I didn’t start this process in the third grade, I wish I’d started it at least twenty or thirty years ago. I always knew retirement and financial well being were inseparable, but only recently have unaccomplished career goals been weighing on my mind. I wish someone had prompted me to consider financial goals and experience goals, to map it out. It’s not the kind of thing I’d have written in ink. There’s some chicken and egg stuff involved. Since I didn’t know what I didn’t know…until I learned…my map would’ve gotten tweaked a hundred times over. Still, being more deliberate about goals, decision making might’ve been different.

Like many careers, mine started out a little haphazardly. I graduated from college with a B.A. in Special Education. Midway through my senior year, I knew I didn’t want to teach, but what’s a person supposed to do so close to the end? I taught for a year, confirming teaching was a “no go”, and left it feeling a bit aimless. One excellent thing about being a twenty-something is a little aimlessness is normal. It didn’t twist me in the wind. I wandered through some time-limited jobs and gave myself time to think. I don’t regret those times, I learned a lot and did some things I could only do single and unencumbered. Still, this would’ve been an opportune time to begin thinking about retirement.

Charting the things most important to me, career and life goals, would’ve guided decision making. Every decision wouldn’t have been laser focused to the goals, but I would’ve been more aware of how close or far away I was. Few careers unfold with precision. Sometimes a job is squarely aligned with career goals, other times it’s squarely aligned with a need to pay bills. I had both kinds of jobs. Each came with a learning curve, clarifying a next step or desired direction. I took a nirvana job that turned out to be hellish. I lost a job. I made compromises for relationship and family reasons. All legitimate, real-world experiences, but haphazard. I often found myself reacting instead of exerting control. I’m curious about what might have been different if I’d made a map.

We all know certain things about ourselves. I’ve always valued purpose over money. I’m not trying to sound lofty; serious hurdles come with such a perspective. I knew I wanted to give back to people and the world but I didn’t have a clear vision for it. In my twenties, I did some faith-based work after my year teaching. In my thirties, I spent time in both the nonprofit and for-profit worlds of psychiatric healthcare. Before I was forty, I made a decision to stay in the nonprofit world. I knew it meant less money but it offered more synchrony with how I saw myself in the world. I was thinking about these career decisions in terms of my values and circumstances. What these decisions lacked was consideration of “what’s between now and retirement?” The map was missing.

Retirement finances began to get more attention in my forties. I had a good retirement plan option at work and I was contributing to it, though inadequately. By then I was a single mom, planning to put two kids through college. I felt like I was doing the best I could. Even though I knew the longer money stays in a fund, the better growth opportunity it has, I felt like I had plenty of time. Twenty years is a long time, right? The financial decisions I made felt reasonable based on immediate circumstances, but there was no thoughtful long term planning.

In my fifties, a whole new set of considerations emerged. My kids were out of school and making it on their own. I was getting my financial house more in order. But…….where was I in my career? I started feeling some vague unease. I ignored it for a while because ignoring is among my more well developed coping skills. Sometimes it works, sometimes it doesn’t. This time it didn’t. The recurring question in my private thought bubble: Was this job going to be where I ended my career?

I was considering for the first time some other give-back-to-the-world goals. I have a standard bucket list. In it are the big adventures, primarily post-retirement and primarily selfish. Things I want to do or experience for me. Turns out, I also have a professional bucket list. I don’t feel done. Career-wise I mean. I love my job but started feeling new anxiety as I edge toward a likely final five to ten years in the workforce.

Two things happened. I read Just Mercy by Bryan Stevenson. When I finished, I was ready to take a sabbatical from my job, rent my house for a year and move to Birmingham to do whatever I could to help with his work. Seriously. I still feel it. However, the practicalities provide a hard stop to damning the torpedoes and full speed ahead. I can’t take a sabbatical for a year; my job doesn’t work that way. My retirement account isn’t fully funded so I don’t have the financial freedom to go for it. Again, I love my job. But does it make me sad I can’t do something like this? It does.

The second thing is less dramatic but occupies some of that same “I’m not done” brain space. I live in Nashville. We’re booming. I love this city. I also see the dark side of the boom. Housing is not affordable for a growing swath of our residents. Public education is underfunded. Public transit looks more like the Flintstones than the Jetsons. There are other big city issues, but these are a few of the big ones. My current work contributes to the health and well being of some of our citizens, but I often wonder what else I could do.

So here I am at sixty, starting to make a map for what I want to do between where I am right now and retirement. The map is created by thinking, evaluating, and asking myself dozens of questions. There won’t be an immutable path, think pencil or chalk instead of sharpie, but it will be deliberately headed toward my goals. My goals will likely change less than a twenty-five or thirty-year-old’s, but the point is making, reviewing and refining the map along the way.

My map is a dry erase board with questions, ideas, and notes leading to my goals. More elaborate questions and narratives will be kept in a separate notebook. I love the emergence of visual note-taking. I’ve been in work groups where a visual note taker drew amazing murals of the content of the entire meeting. It’s almost like a storyboard. I think of a map to retirement like this…words and images…so I’m making this kind of map. A map could just as easily be an electronic document or only a storyboard or notebook. The point is to have one.

Get started!


Here’s a picture of how I’m organizing mine. I pulled three things out as examples. When I fill it out more completely I’ll have 2–3 things in the first two areas and 6–8 bucket list.

Ask yourself some questions:


Where am I in my career? Describe it. For me, it’s toward the end, somewhere in the last decade before retirement.

If you’re early in your career, you may want to spend some time thinking/writing about your level of satisfaction with what you’re doing now. Clarify for yourself whether you’re in the right field of work. If you’re a twenty, thirty or even forty-something, spend some time with this question unless you know you’re right where you want to be. Going back to school or switching careers is easier at thirty than it is at fifty.

What job/position do you want to achieve before you retire? This can change a million times or never. Identifying something gives your path a destination. The destination can change but you need a destination. For me, it’s writing and consulting. Maybe you’re a sous chef but you want your own restaurant. Maybe you’re a teacher and you want to be a principal or school superintendent. You’re a social worker and you want to also be a personal trainer. Maybe you’re exactly in the profession you want to retire from. What goals do you have within your work for excellence?

If you do a visual map like mine (or much better than mine), fill in some milestones with target dates, a few comments, and note the cost and target income. Keep detailed notes/ideas somewhere else.


You can add this as a separate section on your map under career, with targets for large purchases (house, college, dream vacation), retirement savings and/or debt reduction targets.

What’s your current financial condition? Have you started a retirement fund? How much debt do you have? Do you have money left over after expenses every month? Are you good at saving? Your answers to these questions may lead you to making a debt reduction plan, or a saving plan, or to an appointment with a financial counselor. There are tons of online resources and books that can be helpful. Credit unions often have free financial counseling for their members. Employee Assistance Programs many times do as well; check with your employer.

Unpaid professional/career related goals or volunteer goals:

Are there things you want to do to give back? This is where my sabbatical in Birmingham would live. Other things might be serving on a nonprofit board or developing a website for free or volunteering in a classroom once a week for one semester or school year. You may not have anything like this on your radar yet, but ask yourself the question from time to time.

Bucket List:

What’s on it?

Dream things and fun things, big and small. Spend a week in Australia or Iceland. Hike the entire Appalachian Trail in segments by x age. Learn to swim. Complete a triathlon. Go to a Superbowl. Skydive.

If you make a visual map, keep it where you can notice it frequently but not necessarily be seen by people outside your inner circle. Especially if you have friends and family who like to “help”. This is your map! If you keep everything in a notebook or file on your computer, put a reminder on your calendar to review it frequently.

Tell me, where will your map take you?

Writer and metal smith/jewelry maker, Donna has lived happily as a mother, friend, creative, and nonprofit leader in Nashville, TN for more than 30 years. She is additionally committed to her cats, rock climbing, gardening and power tools. She believes that people are good, kindness is essential and artists should rule the world. Find her at
Writer and metal smith/jewelry maker, Donna has lived happily as a mother, friend, creative, and nonprofit leader in Nashville, TN for more than 30 years. She is additionally committed to her cats, rock climbing, gardening and power tools. She believes that people are good, kindness is essential and artists should rule the world. Find her at

Thank you for reading PublishousNOW! We use ad revenue to support this site and would appreciate it if you would please turn AdBlock off. 

pop up opt in

Don't miss the latest

from tomorrow's best sellers. 

You have Successfully Subscribed!

Pin It on Pinterest

Share This