Paving Our Own Way

Growing up, I was taught that life had a set narrative: Go to college. Start a career. Fall in love. Get married. Buy a house. Have kids. Retire at 65. Live happily ever after.

I never much questioned the expectation. Everyone knew that life was better if you followed the rules! And I started off right on track; I went to college, and stumbled into a job. Having a “career” was more of a struggle, but everyone assured me it was normal to flounder at first until you found a fit. Love turned out to be even harder, which put a damper on the marriage part of the equation.

I was in my thirties before I really started to consider that life may not work out the way it was “supposed to”. Following the rules hadn’t gotten me where I expected. I started to question everything: Did I really want to be a “career woman”? Was marriage a necessity? What about kids? If I didn’t find Mr. Right, did I want children badly enough to go it alone?

It took me really questioning the norm before I was able to start letting go of all of my expectations, and really start considering all of the possibilities in life. Would life really be so bad if I wasn’t able to check all of the boxes? I had turned down so many opportunities in my 20’s and early 30’s, because they didn’t fit the expectations of what my life was supposed to look like. I’d never even considered that I could be happy with something different.

I had a lot of uncertainty when Bryan and I first started dating. In some ways, the age gap didn’t matter; We had a great time together, enjoyed a lot of the same things, and could even listen to the same music. But I’d be lying if I said the almost 20 year difference in our ages made no difference. He was struggling with preparing two kids to leave the nest, and I was contemplating the when/if of having children. We both had an idea in our heads of where we should be at, and what we should be doing at this point in our lives. The first few years were the hardest.

We were sitting on the patio one night, early in our relationship, when he mentioned that he could retire in a year and a half. I almost choked on my drink. At the time, I was taking classes for a graduate accounting program. In two and a half years I planned to be completing my degree and really starting to move ahead in my career (spoiler: I didn’t finish the program). And my boyfriend might be retired?!? How was that even going to work?!?

We’ve learned a lot about ourselves in the last few years, and a lot about each other. Bryan figured out that he wasn’t ready to retire, yet. But he really did need to get away from the stress of his job. It wasn’t ideal, but that situation ended up working itself out. He’s much less stressed out now, and enjoying figuring out what he really wants to do. Likewise, I figured out that while I crave change, and feeling like I’m succeeding, a “high-powered career” isn’t really for me. We’ve both realized that Bryan prefers that I have the same flexibility and down-time as him. It’s great when we’re both working, but he’ll drive us both insane if I’m working and he’s not. It’s definitely something we need to consider in planning for the future.

What does all of this mean? It means that we’ve let go of idea of what our lives are “supposed” to look like, and are considering a variety of alternatives. Maybe we’ll both work another 5-10 years, and then retire together. Maybe Bryan will retire and start a small business, and I’ll continue working. Maybe we’ll start a small business together. We have a friend who moved down to Tennessee a few years back. He raises a few cattle, keeps a big garden, and chops his own wood. Honestly, we’ve spent a lot of time down there, and really enjoy it. There’s a good possibility that we’ll spend the next couple of years getting our “ducks in a row”, and then transition into a simpler life, someplace further south.

We still have a lot of loose ends to tie up before we really start planning for our future. But we’re both aware that there are circumstances we’ll need to plan for that don’t affect most similarly aged couples. Even if I wanted to work until my full retirement age, there’s a good possibility I’ll need to leave the workforce at some point to take care of Bryan. If we choose to retire together, we need to be prepared for an “extra long” retirement. After all, even if Bryan retires at 65, and lives to 85, I’ll only be just reaching 65 myself. One of my biggest fears is that Bryan and I will have a wonderful life together, and then I’ll find myself in my 60’s, alone and penniless, and trying to rejoin the workforce. There’s a lot of planning and consideration that we need to do when thinking about pensions, and IRA’s, and 401(k)’s, and marriage, and social security. And kids. But that’s a topic for another day.

It’s exciting, and terrifying, and nothing like the life I imagined I’d live. But it’s full of possibilities. And happiness. I’m happier than I’ve ever been, living a life that I never expected.

And isn’t happiness what we’re all striving for?

– Cindy W.


  1. I don’t have anything constructive to add, but wanted to say that I liked this post. I like the musing about realizing that life doesn’t have to go according to plan to be successful, and also about planning for the future (financially and otherwise.)

    1. Thanks! I know you’re in a similar boat, planning for a life that doesn’t fit the “normal” expectations. I think half the battle is accepting that you don’t have to do things the same way as everyone else.

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