This piece originally appeared on the blog of The Woman and the Owl Foundation, a fantastic group that, "explores and encourages the development of women spiritual leaders of all faiths and backgrounds through education, community, and support." I also did a video interview with them which you'll find here. Many thanks to Jessamine Dana for the opportunity, and to you for reading. - Hillary
I struggled professionally throughout my twenties and thirties. True—I had jobs, and some of them were neat. I was a computer journalist for a while, and also a serial entrepreneur who founded a computer consulting business, a freelance writing business, and a dot-com (remember those?). In none was I entirely comfortable, which probably also explains why in none did I score a solid success.
And so, I hit my early forties somewhat in the wilderness. It wasn't just about having a career—I desperately wanted to make my mark on the world, and also desperately wanted to do whatever I could to help alleviate the world's suffering and injustice.
I'm now 56, and in a completely different, and happier, place. Here's how it happened:
After the dot-com failed—as most dot-coms did—I got depressed and for the first time in my life took to my bed. I spent two months there before it occurred to me that I really ought to get some help.
Six months later, with the help of a good therapist and the support of my then-husband, I was out of bed, and the foster parent of four teenaged refugees from Sudan (“Lost Boys”). (My ex and I had been thinking about fostering for a while, and had gotten our certification the prior year.) That led to three years of chauffering, homework help, buying and preparing vast quantities of food, and all the rest of that “parent stuff.” I also did a lot of volunteer work with the local Lost Boys who were too old for foster care but had the same needs as the younger guys.
It was really all pretty interesting and engrossing and enlightening, not to mention, mind-expanding and fun. I learned vast amounts not just about my kids and their culture and experiences, but the larger refugee and African experience, and also about the more mundane, but no less fascinating, experience of parenting teens. (Me complaining to Other Mom: “I can't believe X kept me waiting at the train station for two hours before he called.” Other Mom: “He called? That's amazing!”) I felt like my brain doubled in size, and all with useful information.
This service-oriented life was pretty much the opposite of the high-tech-mogul life I had always envisioned for myself (but had only vaguely understood or visualized), but along with all the knowledge and fun, it yielded two other important results: (1) it got me out of my own head and the rather narrow set of concerns I had boxed myself into; and (2) it connected me with my community. And it was through my community that I finally got the job that helped me fulfill my professional destiny.
It was teaching and coaching low-income entrepreneurs at a nonprofit in downtown Boston. I'll be honest: at the time, it felt like a real let-down. I had had dreams of wealth and glory; now, here I was, at the advanced-seeming age of 42, working out of a dinky little office in a dingy downtown building, doing work that might be useful but that certainly wasn't celebrated. And so, whenever anyone congratulated me on my new job, I somewhat churlishly brushed their congratulations aside.
Only, that “disappointing” job turned out to be fantastic, and the hinge on which my professional life turned. I quickly realized that, not only was I a terrific teacher and coach, but that these were roles in which I could use my whole person and all my experience and skills. Even my “failures” turned out to be excellent teaching fodder, and a source of empathy and understanding between me and my students—who were, for the most part, interesting people who were highly rewarding to work with.
I had, for the first time, that feeling of being in the right place in the right time, with the right skill set, and working with the right people. It was sublime, and it has never left.
Eventually, I became interested in how I could help more of my clients achieve their business dream, and, after analyzing the forces that typically caused them to derail, added curricula and coaching on time management and overcoming internal blocks to success. They were hits and highly effective; and so, over the past fifteen (nearly) years—in that and a subsequent job, and in my current business—I've continued to refine my focus and develop my expertise in the areas of values-based productivity and time management.
These days, I coach and give workshops all over the world, and am also the proud author of two books, The Lifelong Activist and The 7 Secrets of the Prolific, that together sell hundreds of copies a month. Every day, I work with creative and valuable people, including activists, artists, entrepreneurs, and scholars, which is a joy. And although I'm always hoping for, and working towards, more success, every day I approach my work with satisfaction, purpose, and gratitude.
Do I regret that my success didn't happen earlier? Not really, for two reasons. First, regrets are pointless. And second: because, had I been more successful earlier, I might not have had so much wisdom to share, or ability to share it. As novelist Anne Tyler once wrote* about balancing writing with raising her children, “[My children] may have slowed down my writing for a while, but when I did write, I had more of a self to speak from.”
Most weeks, at least one person—in her fifties, forties, thirties, and—yes—even her twenties—tells me she's way behind where she should be, professionally. I hear her desperation and, of course, empathize. Part of the problem is our society's veneration of youth, and part is perfectionism, which makes us impatient and shortsighted.
But I know these truths:
First, that truly creative and original and caring people often take longer to succeed than those who are conventional and narrow in their interests and concerns. And also,
If you keep an open mind and heart, even long past the time others tell you you should be settled, you will find your path.
And it will be glorious.
*In her essay “Still Just Writing,” from Janet Sternburg's anthology, A Writer and Her Work.