In my everyday life, I’m a planner. I schedule visits with friends, household chores, exercise, and so forth. I mark my calendar and make detailed lists. But when it comes to big decisions, I’ve often acted on a gut feeling and made consequential choices without really knowing what I was doing or how they would turn out. I’ve winged it.

For example, I moved cross-country for college teaching jobs when I was in my 20s. I knew very little about the English departments I’d be part of or the small towns I was moving to. In the first college town I discovered the lack of privacy. Students hounded me about grades at the bar when I was blurry after half a pitcher of happy hour beer. Or they’d chat me up in the drugstore as I reached for a box of tampons. The next college had three different presidents by December, and we worried our paychecks would bounce. Nonetheless, I grew into a competent teacher and made lifelong friends.

When the second college’s financial troubles led to layoffs, I moved back to my hometown to be closer to family. I didn’t have a job but hoped I’d figure it out despite the recession. For nine months, I burnt through my teacher’s pension before I got a job writing training materials—which launched my next career as a marketing communications writer. Once I was employed, my fiancé joined me and we were married in the loving circle of family.

A few years later, I moved away again after my husband got a job in Minnesota because our prospects were limited in Ohio. We started over in an unfamiliar city—with new jobs and a new house but no roadmap for how to be settled and happy there. 35 years later our roots are deep. Our expanding family and circle of friends are here. We happily consider ourselves Minnesotans. Wind chill and all. 

Although I liked the fulltime job I first took in Minnesota, I wanted to have more time with our young sons. I launched a freelance communications business with only one client and nothing but promises of work from others. I knew little about the ups and downs of managing clients and erratic cash flow. 

Fortunately, my husband is excellent with finances. I discovered I had a knack for keeping clients happy and writing about their products and services. I kept my business going for 18 years, but after our youngest son left for college, I wanted to have coworkers again. My collie/office mate was sweet but didn’t have much to say. I took a hospital communications job and enjoyed being part of a large team.

Several years later, there was a reorganization and the joy went out of the job for me. At 61, I didn’t see other part-time career opportunities, so I decided to retire. Although I knew retirement would be major transition, my vision for it was vague. Since then, I’ve built a satisfying life which includes writing, reading, tutoring, gardening, traveling, and plenty of time with family and friends. Occasionally, a headhunter approaches me about work, but I’m not tempted. Retirement life is great!

At each of those turning points, I wasn’t sure how the change would play out. I didn’t have a blueprint to ensure my new life would be OK. I trusted myself to make up my new life as I went along. I’ve made my share of mistakes and endured some tough times, but so far, things have worked out.

These days, I occasionally worry that I haven’t prepared enough for the coming years. We have organized our retirement finances, and we’re actively enjoying life while our health is good. Otherwise, I approach aging in a short-sighted way—with no real plan, just wishes. As if I’m not aging. As if I won’t have to deal with assisted living. As if my own health won’t deteriorate and friends and family won’t get ill or die. I’ve been living life as if I’m not growing older, except obviously I am. 

Sometimes I wish I could prepare for the emotional and physical hardships in my future. Like if I had a plan, I could avoid them. But I know worrying about what hasn’t happened only robs today of joy. I remind myself I’ll figure it out as I go along—just like I always have.