When Will I Do It?

My friend Maery did it after fracturing her shoulder at a company outing.

My cousin Eugene did it when he ran out of staples for his office stapler.

My sister Karen did it when COVID-19 closed the dental office where she worked.

What did they do?

They retired.

But unlike me, they all had employers to retire from. They also all had a key moment when they knew it was time to do just that.

But as a freelance writer who works for dozens of clients, there’s no one employer to retire from and since I haven’t yet had a “now’s the right time” moment, I’m still saying yes to most client work that comes my way. Thankfully, I enjoy the work…and the people I work for.

That said, I am beginning to think more seriously about retirement and what it might look like for me.

Despite the fact that I’ve been dreaming about (and saving for it) since I was 22, I don’t have a very clear picture. That’s one reason why, when I turned 60 three years ago, rather than celebrating with a big party, a piece of jewelry or an exotic trip, I took a one-year sabbatical.

Though I missed having work as a way of structuring my days, I really enjoyed the downtime and the chance to unplug both personally and professionally. I also enjoyed the chance to travel for months at a time.

Although I’ve since returned to freelancing, I now say yes only to projects I can do from anywhere at any time. That way, I still have plenty of flexibility and free time, a lot of which I just putter away. Most days that feels like exactly the right thing to do.

Other days, I’m more engaged. I’ve also started journaling again and gotten reacquainted with art supplies I haven’t touched in years. I’m cooking some and reading more. I’m writing letters and calling friends. I’m even enjoying routine household chores, plus getting estimates for several home improvement projects.

Increasingly, it’s these things—not my client work—that’s giving structure to my days…and no doubt moving me closer to retirement. What sign will tell me that it’s finally time? I don’t yet know, but I do look forward to finding out.

Reflecting on the Business of Being in Business—Ellen Shriner Communications 1993-2011

In 1993, I launched Ellen Shriner Communications when my sons were 1 ½ and 4 years old. I had been looking for full-time work as a marketing communications copywriter and was offered freelance projects. That simultaneously answered the questions: “What should my next job be?” and “How could I spend more time with my boys?” Eventually, I discovered an additional benefit—I had time to take Loft classes, write personal essays and finish a book-length memoir. stacked hat logo

Initially, having my own business was a means to an end. During the next 18 years, it became a huge part of my identity. However, by 2011, I was ready for different challenges, and I gradually shut the business down. Today, as I dismantle what remains of my office in preparation for moving, I’m reflecting on what the business meant to me.

Days when it was great to be self-employed . . .

  • Over the years, I wrote a lot of ads, brochures, direct mail, newsletters, training materials, videos, websites for national clients like Radisson Hotels, Hallmark, Target, US Bank, Medtronic, Sears, Capital One Auto Finance, Eli Lilly, and Pillsbury—work I’m proud of.
  • World Headquarters for Ellen Shriner Communications ;)

    World Headquarters for Ellen Shriner Communications 😉

  • I had the pleasure of teaming up with many talented graphic designers at firms including, InMind Design, Grand Ciel Design, Matt Shimon Creative, Zetah Design, and Fuego Design. We functioned as virtual ad agencies and delivered loads of smart creative work.



  • Some of my work won awards.


Midwest Direct Marketing ARC Awards

  • Being my own boss meant that I could flex my schedule so I could attend my sons’ field trips and Halloween parties.
  • Similarly, I had the flexibility to run errands and manage car or house repairs.

    Tasha, my faithful office mate

    Tasha, my faithful office mate

  • On sunny summer days, I could take a walk or do a little gardening over my lunch hour.

Days when being self-employed wasn’t as great as it sounds . . .

  • Dozens of times I went on sales calls and left them shaking my head at how clueless and cheap some prospects were. More than a handful had to be told “No” when they asked me to work for ridiculously cut-rate prices.
  • Plenty of my clients were so small that you’ve never heard of them—an African entrepreneur, a wedding singer, and a manufacturer of knock-off beauty products—and they had the budgets to match.
  • Sometimes I was in a panic trying to hit my client’s unreasonable deadlines. I’d stay up too late, get up too early, and be jangled by too much caffeine as I tried to power through projects to deliver them on time.
  • No one paid me if I were sick or wanted to take off on vacation.
  • Often I took on projects even if I was too busy or it was inconvenient, because turning down work from good clients drives them away.
  • Equally nerve-wracking were the times I had no work and nothing on the horizon. My billings were bleak after 9/11, when the Great Recession began, and plenty of times in between.
  • Working alone was isolating—an unintended consequence of being a sole proprietor.

After 18 years, I was growing restless. My guys were in college and I was ready for something new. So when a client offered me a part-time job writing marketing communications, it seemed like the perfect solution. I could continue my writing career while maintaining my part-time flexible lifestyle. I’d be paid every two weeks (no more scrambling for billings!) and receive paid vacation and holidays.

At first, I couldn’t get used to the idea that when I left my desk at the end of the day, I was done—no more working nights or weekends! I thought I would miss my home office, but having professional colleagues has more than made up for it. Besides, working in your bathrobe is over-rated.

I was incredibly lucky to have professional work and the flexibility to be with my guys as they grew up. I’m grateful, too, for the time to pursue my literary projects. Today, Ellen Shriner Communications is a proud memory, but Ellen Shriner, Writer is alive and thriving.

The World Headquarters for Ellen Shriner, Writer is wherever I carry my laptop

The World Headquarters for Ellen Shriner, Writer is wherever I carry my laptop

On Losing My Ambition (Open Letter to 35-Year-Old Hiring Managers)

Recently I had dinner with my friend C., who mentioned that after years of freelance writing, she was interviewing to be a marketing communications manager—a position she’s eminently qualified for.

She confided that during the preliminary phone interview, the interviewer expressed concern that C. wouldn’t be satisfied with being a mid-level manager. Perhaps C. would be uncomfortable taking direction from the younger director of the organization. C. paused during this anecdote, with her eyes wide and eyebrows raised. We both burst out laughing and couldn’t stop.

“Being the director is the last thing I want! I just want to do the kind of work I’ve been doing . . . but someplace else. For me, learning the rhythms of that office will be challenging enough,” C. said and paused for a sip of white wine.

“I know! I just want to do interesting work with coworkers I like and be respected for what I know,” I said.

I’m not sure when I lost my ambition for climbing the corporate ladder, but it’s been gone for a while.

womanclimbingladderEven saying that feels odd. I have always cared about my career, and I’ve gone to some trouble to have one (got a graduate degree, made several cross-country moves in pursuit of jobs, been a working mother). But I simply no longer have a driving need to be promoted. Unlike Sheryl Sandburg, who encourages working mothers to be all they can be career-wise (see Lean In), I leaned back a long time ago.

When I was in my 20’s and early 30’s, my career was my main focus. But my priorities broadened after my sons were born. Instead of pursuing a classic corporate marketing or ad agency path, I launched my own freelance writing business. Would I have made different decisions if the workplace had been more flexible? Maybe. But having my own business worked well for me—stacked hat logo

a) It gave me the flexible hours I wanted when my sons were growing up so I could be a bigger part of their lives. They spent fewer hours in daycare. In the summer, I’d occasionally knock off early and we’d go on excursions—the beach, the zoo, or the park. When they were sick, I’d be home. I still had deadlines and needed to work late after my husband returned from his job, but it was easier to manage. Plus, I could volunteer at their school and go on their field trips.

b) With half a dozen clients, I could have the creative variety that’s often lacking for ad agency copywriters. Instead of being the head writer on the agency’s Visa team, I’d write for Land o’ Lakes, Visa, Radisson, Medtronic, Sears—whichever account was active that week.

c) As a freelance writer, I had more free time to write personal essays and memoir pieces—the kind of creative writing I’d always wanted to do.

I made choices that supported the life I wanted; my decisions did not advance a traditional career path.

Shortly after my second son was born, while I was still working full-time, I was offered the opportunity to be promoted from senior copywriter to associate creative director. It was hard to say no—at that point I still had traditional ambitions and wanted to advance. But I turned down the promotion, because between work and family, I was already at or beyond full capacity. I simply didn’t have the energy to do more and to do the job justice.

Several years ago, I chose to leave my freelance business behind (it stopped being as much fun and my sons were grown) and take a part-time job writing marketing communications for a children’s hospital. I’ve had several chances to go full-time and get back on the classic path to career advancement. Ambition flickered in my heart. I briefly heard the siren song of advancement, “You’ve got more in you–you’d be good at that job.”  But I leaned back again. New logo 2

I have other goals and responsibilities now—

a) Having the flexibility to help my siblings care for my 91-year-old mother in Ohio

b) Having fun with my husband who recently retired

c) Making time for my creative writing projects

As I told C. during dinner, “Hiring managers don’t have to be so worried about Baby Boomers. A lot of us don’t want to take over anything. Work is just one of the things we care about. We have a number of priorities.

C. and I raised a toast to that reality.