Thoughts on Being Middle-Aged and Finding Happiness and Success

I’ve never been a maker of plans or a setter of goals. Oh, I know that’s what you’re supposed to do, but it’s just never been my way. Some people are obsessive list-makers. Others, as my friend Janet Fouts writes, are their own critical monsters, sabotaging themselves without intending to. Others methodically plan out what they’re going to accomplish by a certain age and hold themselves dearly accountable. As an example, one of my dearest friends was bound and determined that she HAD to be married by the time she was 30, and she moved mountains to make sure that happened. By the way, her wedding anniversary is November 1st and her 30th birthday was November 3rd of that same year. Goal, plan, execution. That has never been me, not at 20, not in my 30s, nor at any other age along the way. Which is partly why I’m writing about being middle-aged and finding happiness and success. It happens, and if you’re frustrated because you don’t think you’re ‘there’ yet, relax. You’ll get there, I promise.

Happiness, Career, and Success

So let’s talk about it. Let’s start with happiness, career, and success. I was a young mom, and from the age of about 26 onward, raising my kids as a single mom. I didn’t spend a lot of time strategizing about my career and success. I certainly didn’t spend much time thinking about happiness. I found a job I thought I was going to like, in a field I thought I was going to like, and proceeded to learn everything I could. I worked hard, built a strong network of friends and business connections, and set about making my way. I wasn’t thinking about a plan—I was too busy doing to plan. I was also too busy scraping a living together to keep a roof over my kids’ heads to plan.

I’ve never make lists or set goals, I’ve just somehow managed to trust in myself and hope I’d figure things out along the way. I mostly did. I started my own company when I was 34 and I’ve never worked for anyone but myself since then. That doesn’t mean it’s all been a breeze—far from it! There have been tough times, stressful times, and times I’ve wondered where my next nickel is coming from, and times I’ve wanted to throw in the towel and go find a job working for someone else. Every entrepreneur will say that—it’s part of the experience of building a business—the good, the bad, and the ugly.

What about you? How do you handle difficult times? During difficult times my strategy is always to take a whole bunch of deep breaths and try to relax. My goal during those times is to try to go to sleep at the end of the day and remind myself (sometimes repeatedly) that tomorrow is another day. “Tomorrow,” I tell myself, “things will look better and things will be better.” And you know what? In most instances, things do look better in the morning. For some weird reason, I know that even when I don’t exactly know what the answers are, I’m pretty sure I’ll eventually figure them out, and that everything will be okay. That’s largely been the case, Not obsessing about a goal or an obstacle, but trusting in myself that I’ll get to where I want to be by taking it one step at a time. I know that approach doesn’t work for everyone, so tell me, what works for you?

What is Success? It’s Different for All of Us

I realize that success means different things to different people. Success looks different, and if feels different to all of us—and it will come when it comes. I’m lucky in that going loose and just and just rolling with it—meaning whatever life has in store for me—has pretty much always led me to something good. It could also be that I’m a ridiculous optimist, and inclined to look for the good rather than the bad, so I’m biased on this front. In any event, whenever something bad has happened, like I’ve lost an opportunity or a big client, or I’ve made a bad investment or misjudged someone I thought I could trust, or been disappointed in some gigantic way, something good has always been right around the corner.

My success has always been personified by chaos, even today. I love it when things are fast-paced and demanding and almost a little insane. I love change and learning new things and taking risks. I remember after having twins almost thirteen years ago, I had to completely rebuild my consulting business, pretty much from the ground up because I quit working for about eighteen months when they were born. Once I was ready to rebuild, I took on a couple of clients that I really couldn’t stand, but I had to endure working with them as it was part of my way back. I remember trying to work from home while my kids were sleeping, and them inevitably waking up and screaming for attention right when my biggest client wanted to have a conference call. The only place I could go to take that conference call that was quiet was the cedar closet in my basement, where I could talk and not hear them screaming at the top of their lungs two floors above me. I had to laugh even then at the ridiculousness that was my life, because it was pure chaos. But that chaos was part of my success story then, and it’s part of what success looks like for me today. I’m grateful to be able to have built a life that allows me to be an entrepreneur and a working mom, raising my kids in as much of a hands on way as humanly possible. Was it hard when they were little? Hell yes. Is it still hard? Hell yes. But would I trade it for anything? No way!

That’s the thing about success—it’s different for each and every one of us, and there’s no right or wrong answer. Only what makes us happy, fulfilled, and loving life. For me, success has always been defined as being able to do what I love, with people I like and respect, and being able to apply my talents in ways that make me happy and make other people successful. Being able to do that and raise my kids and be as involved as possible in their lives without leaving them in the hands of others more than absolutely necessary (like I did with my first two daughters when they were little), has also been incredibly important to me. What does success look like, or feel like, for you?

Middle-aged Success?

Success at middle-age? You bet that’s a thing. In fact, it’s a big thing! For me, while I wasn’t quite middle-aged when I started down the career path of owning my own company, it wasn’t long before I was middle-aged. Sounds weird, doesn’t it, to think of your late 30s as being middle-aged, but hey, do the math. In your late 30s, you’re mathematically in the middle of your life. By 40, you are definitely middle-aged. Deal with it.

Some of the happiest people I know realized their greatest successes at middle age. Look around, I’ll bet you can say the same. My friend, Anne Weiskopf, founder of Make Your Now Wow, had a rough few years in the last decade, and now in her 50s, she’s doing something she never dreamed about doing, and happier than ever. My friend Bonnie Marcus, author of The Politics of Promotion: How High Achieving Women Get Ahead and Stay Ahead, has a new book in the works about women over 50 in the workplace, and it’s sure to be filled with success stories of inspiring women achieving success in middle age. Bonnie is going to join me on the Middle Chicks’ webcast in a few weeks, and that’s one interview you’ll not want to miss!

Beyond my awesome friends, some pretty famous people didn’t achieve success until later in life, either. Don’t believe me? Let’s take a look —

Laura Ingalls Wilder started working on her memoir when she was 43, and it wasn’t until she was 65 that she published her first book “Little House Big Wood.”

Vera Wang didn’t start thinking about becoming a wedding gown designer until she was (gasp) 40.

Toni Morrison was a single mom working for Random House as an editor – and her first book wasn’t published until she was 40.

Viola Davis didn’t land her breakout role in How to Get Away With Murder until she was 49, and her performance in that role led to her being the first black woman to win an Emmy for Outstanding Lead Actress in a Drama Series.

Designer Vivienne Westwood, often referred to as the “godmother of British fashion” wasn’t on anyone’s radar screen until she designed her ‘mini-crini skirt’ … the year she turned 50.

Actress Connie Britton brought Tami Taylor to life in what is arguably one of my favorite TV series of all time, Friday Night Lights (Texas Forever), when she was 39.

These ladies? They’re killing it in their respective careers. And there’s a long list of other people who didn’t ‘make it big’ until they were middle-aged, or older.

What the Research Says About Entrepreneurialism and Middle-Age

Success stories are nice and all, but research is nice, too. According to a study done by MIT Sloan School of Management, the average age of successful entrepreneurs in the U.S. is about 42 (which is definitely middle age, people)!

A study by the National Bureau of Economic Research found that entrepreneurs starting successful high-growth firms tend to be middle-aged or older, and that a 50-year-old founder is almost twice as likely to achieve a successful exit as a founder at 30. Well done, fellow middle-age entrepreneurs. There’s a ton of data on this front, so if this is of interest to you, I highly encourage you to dig deeper into how middle-aged people in general are more likely to successfully found and lead entrepreneurial ventures to success and/or acquisition. It only makes sense. Middle age means experience, knowledge, network, instinct — all the things that take time to happen. Being middle-aged and finding happiness and success isn’t as hard as you think.

This whole concept, the thoughts on being middle-aged and finding happiness and success was inspired by an article written by Ann Dowd published in Glamor magazine following the 2018 Glamour Women of the Year Summit event. Ann is one of the stars of the wildly popular Hulu original series, The Handmaid’s Tale, and is one of Glamour’s honorees this year. In Ann’s article, she talked about what it was like finding success later in life—in her middle 50s, to be exact. Her advice is lovely, and something we should all take to heart: Stay humble. Stay grateful. Believe in yourself. Have unshakeable faith in yourself. Ann’s best advice is at the end of the article, and I’m going to link it here and suggest that you read it. In fact, I’m going to promise you that this will be the very best thing you’ll read all week. Believe in yourselves, darlings. It will happen. Whether you’ve got a plan or whether you’re on the non-plan plan program. I promise.

Glamour: Actress Ann Dowd on What It Was Like Not Finding Success Until Her Fifties

And here’s an excerpt of one of my favorite parts of Ann’s story:

Keep your love story alive—and by love story, I mean the love you have for the work that you do—for it is a pure and powerful dynamic, and it will sustain you. Pay attention and take care of it. We are here to do the work we are able to do, the work we love to do. It doesn’t mean there won’t be ups and downs; there will be plenty of them. Keep the love story alive.

Ann is pretty awesome, isn’t she? Make sure you go read the rest of that article, too.

Other stuff you should probably read:

Why Middle-Aged Entrepreneurs are Better Than Young Ones

Three Lessons You can Learn from Ruth Bader Ginsburg on Ambition

14 Wildly Successful Women Who Were Late Bloomers