To: M'Cues Readers

Published: December 5, 2021

Midlife Cues masthead

Buon giorno, my reader friend. Welcome to the 90th issue of Midlife Cues, a weekly newsletter that explores the well-lived midlife. I appreciate you being here. Was this email forwarded to you? Thank the awesome person then sign-up for your copy here


A close friend is getting ready to retire from corporate life in a couple of years.

The plan is to travel for the first 6 months. After that, she goes to work. Slowing down and taking it easy for the rest of her retirement? Not in the game plan.

She wants to start a business as a “post-career career”, as she calls it, and said she’s done with having a boss. For a while at least.

“Isn’t it glorious, being your own boss?” she asked/told me.

So, knee-jerk response: YES, YES, YES. For all the reasons you can only imagine if you’ve been an employee all your professional life.

But… (aren’t there always buts?)

One thing I realized when I jumped into this seemingly glorious pool: we’re not always the best bosses of ourselves. 🤭

Sometimes, we can be as infuriating as the bosses we’d love to leave behind.

I know there were things I did initially that would frustrate me to hell and back if some boss of mine did them to me. Things like:

  • Being wishy-washy, as in not able to decide whether to go with A or B and flip-flopping between the two;
  • Being completely unrealistic, as in taking on too much and expecting me to complete them all with flying colors; or
  • Being such a perfectionist, as in never being satisfied unless every single corner is made perfectly square.

(Who am I kidding? I still catch myself doing these things!)

This conversation with my friend got me thinking about lessons learned and I ended up writing this short piece on realities of being our own bosses. If you’ve ever only been an employee (no diss there!) and you’re starting a business for the first time, some of these truths may be helpful.


I don’t want to sound discouraging. If going on your own is on your midlife list of hills to climb, more power to you. Look for me on the sidelines waving the pom-poms.

Starting a business, being my own boss, has been the hardest thing I’ve ever done in my professional life, hands down. AND I would choose to do it again in a New York minute. I’ll just maybe do it a bit smarter in some areas and aim for being a kinder boss to myself.



I discovered Scribd last year and thank goodness for that! If you’re familiar with Kindle Unlimited, it’s a similar concept — only better. You get to borrow as many books as you want to read. But unlike Kindle Unlimited, you also get to borrow audiobooks. (With amazon, you have to open a separate Audible account.)

In addition to books and audiobooks, you also get to borrow magazines. And you get to read all these on your smartphone or tablet.

Give it a spin with this 60-day trial period. Easy peasy.

  • “Baby Boomers just can’t seem to quit … working, that is. It’s not that they can’t afford to retire. It’s just that they’re finding out it’s not all it’s cracked up to be. I’m guessing that our [generation’s] reaction to retirement will end up similar to what the Boomers are currently paving the way for.” How Will the “Unretirement” Trend Affect You
  • One of the biggest work-related news stories in recent months is the Big Resignation—which I’m happy to say is something we discussed here on Midlife Cues waaaay before it was mainstream and everybody and their uncles were talking about it (just sayin’). 🤭 There appears to be another side to this story though. While loads of people are re-examining their work situations, many retirees are unretiring and apparently returning to the labor market.
  • One thing I’d do differently if I had a chance of a do-over, is to work on my network before I left Corporate America. I had what I thought was a pretty strong network at the time, but it was almost entirely comprised of people from my corporate life. I didn’t see that I needed to build a new network until it was like a red flag waving in front of my face. Build a Network—Even When You Don’t Think You Need One
  • “It’s hard to get back into the traditional workplace after 50 if you were forced out. Starting your own business puts you back in the driver’s seat. In fact, with a few more years under your belt, you have more of an edge than you think when it comes to starting a business.” Here are seven tips for starting a business in your 50s and beyond.
  • We’ve all heard the old saying, “It’s lonely at the top.” It’s lonely being the CEO. But Reid Hoffman, co-founder of LinkedIn and host of Masters of Scale (one of my favorite podcasts), says being an entrepreneur is even lonelier. “I often say that starting a company is like throwing yourself off a cliff and assembling an airplane on the way down. That’s terrifying enough. But even more terrifying is the fact that you’ve convinced an entire community of people you care about to throw themselves off the cliff with you.” In this LinkedIn post, Hoffman offers a few tips on Entrepreneurship and Loneliness.


“You don’t learn to walk by following rules. You learn by doing and falling over.” —Richard Branson


What do you think about the idea of “unretirement”? Is it in your cards? Hit ‘reply’ and let me know. I’d love to hear from you!


Back in 1989, you logged on to AOL … for the, you know, internet… and if someone was nice enough to have sent you an email, you’d have heard the dulcet tones of some guy go, “You’ve got mail.”

That guy was Elwood Edwards, a broadcast announcer who was volunteered by his wife, at that time a customer rep for the company that was to become America Online.

Ten years later, in December 1998, the romantic film by Nora Ephron, “You’ve Got Mail” was released, reuniting the official 90s cutesy couple, Tom Hanks and Meg Ryan for the third time.


MC reader and dear friend, Yvonne Marchese invited me to join her on her Late Bloomer Living podcast and we got to talking about midlife reinventions and letting go—in my case, both figuratively and literally.

We recorded this convo in August, a few weeks before I closed up my Florida life to temporarily relocate to the Philippines. It was such a gift to hear one’s state of mind just before the big leap to the unknown 🤣

Anyhow, if you’re curious about my midlife reinvention journey and especially the latest crazi-, I mean adventure, have a listen here.

BTW, Yvonne’s podcast is a treasure trove of inspiring midlife journeys. Do consider adding Late Bloomer Living to your podcast 🎧 roster.


Thought you might find it interesting that the most popular link from last week’s issue was this one: The Most Effective Way to Thank Your Significant Other

And I heard from a few reader friends that they forwarded the article to their spouses/partners. So there’s an idea 😉

Here’s to an easeful and joyful week ahead.

Cool beans,
Lou Blaser

P.S. If you like reading the newsletter and what to support it and me, you can buy me a coffee! 🧡


A former management consultant and IT leader, Lou Blaser is the editor of Midlife Cues and the host of the Second Breaks podcast. She is also the author of Break Free: The Courage to Reinvent Yourself and Your career. Lou’s work is focused on exploring how to navigate, thrive, and turn midlife into the best phase in our life.

Subscribe for more midlife goodness in your inbox every Sunday.