As I approach my 60th birthday, this milestone invites time for reflection, both personally and professionally. Do I have any regrets? Would I do anything differently? I launched into adulthood in the 1980s and ’90s. I graduated high school, went to college and graduate school, got a job, started a family and bought a house.
But, with hindsight as the best teacher, I’d both applaud and tweak some of my choices. After a little self-reflection, I discovered 10 lessons I’d share with fresh-out-of-college me—who, at the time, was brimming with ambition and naiveté. Here’s my advice for my younger self.
1. Stand up for yourself more
Assertiveness was never my strong suit, especially when I was younger. I remember one instance when I applied for a communications job and the male interviewer asked if I was pregnant or planning to have children soon. My face turned bright red, and I was caught off guard and embarrassed at this deeply personal question.
I didn’t know that discrimination against pregnant workers became illegal when the Pregnancy Discrimination Act (PDA) was introduced in 1978. Back then, I meekly answered this highly inappropriate question. Today, I would have admonished the guy and abruptly ended the interview. I’ve discovered that assertiveness—without compromising kindness, respect or professionalism—is empowering.
2. Skip the master’s degree
What? Eschew higher education? While I enjoyed graduate school, met some wonderful people and found my studies enriching, the advanced degree failed to yield tangible career benefits. If I’d continued climbing the corporate ladder, I’m sure my master’s degree would have eventually paid off. But as a freelancer, it honestly didn’t make a difference. In hindsight, opting out of grad school could have spared me significant time and saved me thousands of dollars. But at the time, I did not envision a 35+ year career path as a freelance writer in charge of my own success. Live and learn, right?
3. Play to your strengths
Initially, I leaned into my master’s degree in public relations. But what I really loved was the writing aspect of the job. I didn’t like being on camera or giving live radio interviews. I didn’t enjoy the media blitzes to hand out (printed!) press kits and schmooze the editors with desk-side appointments.
I enjoyed—and still thrive on—the behind-the-scenes work of researching a topic, interviewing experts, writing and storytelling. While I appreciated learning about the PR side of the business, my heart was on the writer’s side. So, after two full-time public relations roles, I decided to become a full-time freelance writer. While I paid my dues early in my career writing about topics I didn’t love or working with clients who weren’t a good fit, I’m now privileged to pick and choose what I want to write about and whom I work with. Leaning in hard to your strengths is great advice to your younger self.
4. Don’t put off parenthood so long
Most of my 20-something friends started having kids soon after getting married, but my husband and I weren’t ready to take the parenting plunge yet. Though we married in 1988, we waited 10 years to start a family, which I’m sure felt agonizingly long to our parents.
We consciously prioritized our professional aspirations and relished the freedom of our child-free lifestyle. We traveled, bought a Jet Ski, joined a volleyball league, threw parties and regularly met friends for dinner and drinks.
Little did I know, my dad would pass away from cancer at age 54—years before my first son was born. And my mother-in-law passed away when my second son was just a few months old. Neither of my boys got to meet my dad, and they were too young to remember my mother-in-law. Looking back, I wouldn’t have delayed motherhood for so long.
5. Balance work and family better
Once my husband and I finally did start a family, I decided to prioritize family over career for a while. I put my freelance writing on hold, allowing me to savor my boys’ childhood as a stay-at-home mom. I also decided to homeschool them off and on for 10 years.
I did some occasional freelance gigs, tackled sporadic projects and took on some marketing-related volunteer work. But those parenting and homeschooling years consumed me—I was all in being a mom and teacher. While I don’t regret my decision to put family first for a bit, I do wish I’d continued my freelance writing consistently. Instead, I lost touch with my professional network, fell behind on technology and had to basically start over as a “seasoned newbie” at age 50, despite having decades of experience.
To all the someday-moms reading, take this message to heart: Find ways to keep your toe in the professional world while raising your young brood.
6. Ditch the idea of job security
In my generation, “job security” was still a real thing. The concept of getting hired at a company you loved—then working your butt off to exceed your boss’s expectations—equated to spending decades at the same company. Now, the idea seems quaint. But in my 20s, I remember telling my entrepreneurial-minded husband that I’d never want to work for myself: It’s too risky, too scary. I wanted the “security” of a job.
Ironically, I ended up spending the next 35 years as a freelancer. Now, as I watch the media industry implode, see companies downsize or fold completely, feel empathy for so many people getting laid off and read stories about pay inequity between men and women in similar roles, I’m so glad my business, my income and my future rests solely in my hands. That is real job security.
7. Strengthen those left-brained skills
As a writer, I’m all about storytelling, creativity and out-of-the-box thinking. Engaging in these activities makes my heart sing. You know what doesn’t make my heart sing? Analyzing data. Doing taxes. Setting budgets. Understanding legal contracts. Really, anything involving numbers.
So, instead of improving my skills in these areas, I’d avoid them whenever I could. I’d either rely on my husband (who is a unicorn with incredible left-brain and right-brain superpowers) or I’d outsource these hated tasks to others, like accountants. While it’s smart to outsource certain parts of your business, it doesn’t mean you should avoid trying to understand them better. Play to your strengths—but shore up your weaknesses.
8. Be the mentor you wish you had
By no means do I claim to be the voice for freelancers everywhere. I’m 60 and still learning new things decades into my career. But some foundational skills never change, and some common struggles remain.
I love helping “newbies”—and that doesn’t just mean the younger generation; many people are switching jobs and even industries—multiple times in their careers. Others are taking on side hustles. Still others hope to stave off the boredom of retirement, launching blogs, podcasts and YouTube channels to feed their souls. Why not share what I’ve learned since I started freelancing in the (gulp) 1980s?
That’s why I just launched a free newsletter to do exactly that—share what’s worked (and not worked) for me as a freelance writer for decades. Called Expert•ish Freelancer, the newsletter aims to help others launch or elevate a freelance writing business. Of course, it will provide practical things (like tools, tips, insights, resources, etc.). But it will also help instill confidence so freelancers don’t get waylaid by imposter syndrome. That feeling of self-doubt can really limit potential and stifle dreams.
9. Continue embracing the ‘learning mindset’
I was always that oddball student who looked forward to the new school year. Besides the opportunity to buy some new school clothes and get a pair of new shoes, I absolutely loved learning. Unlike some people who stop reading once they graduate, I’ve continued to learn my entire life. I’d sign up for courses, visit the library, participate in workshops, get certifications, join professional associations, attend conferences and, of course, continue to read.
This approach has served me well—and still does. These days, I’m learning how to create a digital newsletter, improve my LinkedIn presence, leverage AI and master the ever-changing iOS platform on my iPhone. Learning opens the door to new opportunities, connections, perspectives and skill sets. Why would I ever want to stop that?
10. You do you
One of the best compliments I ever received came from a friend who praised me for being so authentic. She gushed about me being genuine, down-to-earth and unpretentious. I wear these traits like a badge of honor, but honestly, that’s just me being me. I don’t try to be authentic—I just am. I’m not into playing games.
I don’t worry too much about what other people think. I don’t fall prey to being a people pleaser at my own expense. I don’t let others’ goals, paths or expectations color my decisions. I take some risks that push me a bit outside my comfort zone. I often zig when others zag. And I never want to change.
Photo courtesy of Lisa Beach.
