I recently read somewhere, “If you don’t like starting over, stop giving up.” At first, I was taken aback. After all, I’d only just started a blog on the subject of starting over in mid-life. But then I thought, “Wait—there can be all sorts of reasons one might start over that have nothing to do with giving up.”

I’ve started over several times in my life. I don’t care how many people say it’s exhilarating; putting oneself out in the world in a new way is always hard, and I find harder as I get older. I’m not sure if that’s because I don’t have any personal role models for starting over late in life; among my family and friends, everyone did what they did until they died or retired.

Maybe it’s because I’m an introvert—a person who recharges their batteries by being alone, as compared with extroverts, who get their energy from being with people—and starting over typically requires energy to put oneself out there. It’s not unusual for people to have less energy as they get older, whether from a naturally slowing metabolism or because they’re dealing with personal, professional, or health issues.

More likely, I think anyone who starts over in mid-life finds it hard, in at least some respects, but doesn’t necessarily talk about the hard parts. I’ve never been a member of the say-only-positive-things-all-the-time school of thought. Almost inevitably, when people subvert so-called “negative” feelings and experiences because everyone else would rather only hear about the “positive” ones, they enlist unhealthy coping mechanisms.

The problem, of course, is that difficulties only become more difficult when they’re not talked about, but it’s all the more difficult to talk about them when no one else is taking a risk and talking about them lest others target them for not being positive enough. North American culture, I find, is as obsessed with non-stop positivity as it is with relentless self-sufficiency, effortless perfection, and endless youth and beauty. But that’s a whole other rant.

Getting back to the many reasons one might start over, I started over as a youth worker after university because I realized that, although I loved studying anthropology and archaeology, I wasn’t as drawn to the career options as I’d thought I’d be (and wasn’t aware of some of the other options that might have been open to me).

I stumbled from there into youth work almost accidentally. It influenced the course of my life in countless ways, but after seven years I was burning out. Besides, I’d always wanted to be a writer; it had been in the back of my mind for years, but I’d always felt like I needed more life experience. After university, archaeology, travel, youth work, and marriage, I felt ready. It was time to start over again.

I set about to be a freelance journalist around the same time I started my family and stuck with it for 12 years, until our third child came along. At that point, I still wasn’t making a living—freelance gigs were already becoming scarcer and more poorly paid, and I finally had to admit it wasn’t just a personal failing and put my family first. So I started my fourth career, as the sole proprietor of a communications business, working with small nonprofits, with a long-term goal of getting back to creative nonfiction writing after the kids were older.

That’s what I’m doing now, though it feels more like “starting over” than “getting back to it” at least partly because the publishing world has changed much more than I anticipated 20 years ago—and, frankly, so have I. And all those changes make it more difficult than I thought it would be, to the point that I have many moments of regretting that I ever left writing behind.

When I look back with hindsight, I can see there was a third road. On my bad days, I feel bitter because the choice not to take that road wasn’t entirely mine. On my better days, I remember doing what I felt was best for everyone and I remind myself that harbouring anger over old choices doesn’t change anything, past or present.

I imagine a lot of people have those sorts of feelings, which is why I think talking about them is a good thing. The point is, though the statement “If you don’t like starting over, stop giving up” took me aback when I first read it, I soon realized it only sounds true until you think about it.

Anyway, I’d forgotten all about it until I read an article in the Globe and Mail last weekend about an accomplished writer who started over as an Anglican priest in her fifties. It was something she’d always wanted to do, something related in many ways to what she’d been doing all along, something that continues to carry on aspects of life she’d started much earlier. I found it a good read.

It sounds like a completely joyous journey for her, and maybe it has been. Some people really are relentlessly positive, while others battle depression and “negative feelings.” But maybe more of the latter would find the courage to start over in mid-life if they knew more about others who are doing it, and that having/sharing fears and negative feelings about it is not a bad thing. It’s not a sign that the only reason you’re struggling with starting over again is that you’ve spent a lifetime giving up.

I’ve started over many times, for many reasons. None of them had anything to do with giving up. It’s difficult starting over now, but I want it, so I’ll stick with it. I hope it will be my last start-over, but if I’ve learned anything in life, it’s that you never know what’s coming up. You never know when life is going to throw a start-over at you, you never know how you’re going to feel about it until you get there, and it’s probably better not to judge people who are in the process of finding out.