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The Grass Is Definitely Greener.

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AUTHOR: Mark Crothers on 1/07/2026

I’ve been doing some consulting work with my former business again. This time, I’m helping the new owners navigate the fun of year-end tax reporting using the IT systems that had grown organically over the years, systems that made perfect sense to me but turned out to be anything but straightforward for them. What I could do almost on autopilot required careful explanation and documentation beyond what I’d already provided. It seems my “logical” system only made sense to me.

It’s a strange experience, once again, revisiting the business I started nearly thirty years ago. New faces everywhere, a different atmosphere, different rhythms and priorities, it’s only been nine months since I sold up and retired, but it might as well be nine years. I felt like a friendly ghost wandering through the house I’d built brick by brick, and the dislocation was slightly surreal. The place still bore my fingerprints, but it no longer felt like mine…they’ve even got rid of the free coffee machine I installed for the staff!

I think some people look back on their working life with regret when it ends, a nagging feeling that their best years are behind them, that they’ve been diminished somehow. The battles they fought and challenges they overcame during their careers become distant memories, gradually forgotten by organizations that have already moved on without them. For those people, retirement can feel like a pale shadow of their former glory, a slow fade into irrelevance.

But I believe that’s entirely the wrong way to look at it. Instead of dwelling on what’s finished and mourning what’s been left behind, we should look forward to the freedom that retirement brings, the chance to choose our days, to pursue what matters to us now rather than what mattered to the business. No more meetings that could have been emails. No more emails that could have been nothing at all. That’s a much healthier perspective. This second round of consulting work is my final self-imposed moral obligation to help out, although I’ll admit the cash is good!

Heading home, I felt sorry for them. They have years of grind ahead of them, the relentless cycle of problems to solve, deadlines to meet, demands to juggle. My mindset has changed so profoundly that the very thought of doing all that again sent a genuine shudder down my back. Meanwhile, I’ll be parking the car and walking to a local coffee shop to meet some other retired friends for a chat and coffee. The only worry in my world is the fact I might be ten minutes late, and even that doesn’t really matter.

I know which reality I prefer inhabiting, and it’s the one where nobody can schedule a meeting with me anymore. Another few days next week will finish my consulting gig, and then I’ll leave the new owners to sink or swim with their dream of running their own business. It’s hard to believe that was my dream for thirty years; now, it would be the material of my retirement nightmares.

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greg_j_tomamichel
19 days ago

Another great, though provoking piece Mark.

Whilst not retired, I have definitely shifted down a couple of gears. Thinking back to the effort required to run our business, along with some of the exhausting roles prior to that, I’m certainly pleased to be operating at a lower pace.

I’m surprised, but really pleased for you, that you managed to go from such an intense work life to fully retired in one swift move. Anecdotally, it seems like many people need a staged transition to shift their mind and body from one phase of life to the next.

DrLefty
20 days ago

Since someone quoted Philippians below, I’ll go Old Testament and quote Ecclesiastes: “to everything there is a season…” (and no, that was not original to Pete Seeger or the Byrds, but you’re welcome for the ear worm you’ll now have the rest of the day).

I am ecstatically happy to be retired after a 35-year career as a professor, but I’m well aware that younger academics in the thick of theirs, or my recent students just starting out, would not relate to this. I’ve been them. I was very, very immersed in it for a long time, and it (mostly) gave me a sense of purpose and a lot of satisfaction. I don’t miss it (somewhat to my surprise), but I certainly don’t regret it. I feel simultaneously grateful but ready to move on.

I’ve had similar thoughts as I moved through the “seasons” of parenting. I remember being pretty ecstatic as a new empty nester: we’d drive by the soccer fields on a Saturday morning, where we’d put in lots of time over the years, on our way to a leisurely brunch on a restaurant patio, followed perhaps by a movie matinee—and feel a bit smug. But I wouldn’t have wished away the hands-on parenting years while they were happening (OK, maybe some of them!). You have energy and enthusiasm for different things at different stages of life. Turn! Turn! Turn!

Last edited 20 days ago by DrLefty
mytimetotravel
21 days ago

Welcome to a happy retirement. I have never looked back, and had pretty much forgotten about my work life until I moved to the retirement community, and the people I was meeting asked about it. A new friend, learning that I had been a techie, recently sent me a coding puzzle. I replied that I hadn’t written code in 25 years, and these days I did word puzzles.

mytimetotravel
21 days ago
Reply to  Mark Crothers

You seem to have made a good recovery from the temporary distractions! There are always paths not taken….

quan nguyen
21 days ago

Mark, it’s official: you’re cured of the old place. You’ve traded your prior preoccupation for a much-deserved post-occupation.

Welcome to the greener side of the hill.

Langston Holland
21 days ago

I think some people look back on their working life with regret when it ends, a nagging feeling that their best years are behind them,”

But I believe that’s entirely the wrong way to look at it. Instead of dwelling on what’s finished and mourning what’s been left behind, we should look forward to the freedom that retirement brings,”

There is no more important point that has ever been made on HumbleDollar than this one. This is the essence of life lived well, lived as designed. Anyone here that is not engaged in something that deeply stirs the blood, start now. These are the best days of your life.

Brothers and sisters, I do not consider myself yet to have taken hold of it. But one thing I do: Forgetting what is behind and straining toward what is ahead, I press on toward the goal to win the prize for which God has called me heavenward in Christ Jesus.” – Philippians 3

Dan Smith
22 days ago

Mark, I’ve been gone from my job at the beer distributor for 24 years. Today I will have lunch and a few beers with five or ten of my fellow “ElderBeerMen”. I enjoy these retiree lunches, however, a couple years ago I played in a golf outing with all the current employees and felt just as you did, walking through your old world. No way do I miss that grind. 
I have read many articles regarding the importance of maintaining strong social contacts in retirement. I hope your well written and entertaining article reaches someone who needs a little nudge in the right direction.

Dan Smith
20 days ago
Reply to  Mark Crothers

🤣For sure I thought you were going to say the “crew” was the most important! But you’re right. It’s the beers🤣

Chris Rush
21 days ago
Reply to  Dan Smith

Love the “ElderBeerMen” moniker!

Dan Smith
21 days ago
Reply to  Chris Rush

Some background on the ElderBeerMen:
https://humbledollar.com/2024/06/after-all-these-years/

Scoot Home
19 days ago
Reply to  Dan Smith

Dan, I think you should expand your ElderBeerMen membership by going to Ireland and initiate Mark by having a few pints in an Irish pub. I would have suggested having Mark come to Toledo, but, well, it’s Toledo… (just kidding!)

Dan Smith
18 days ago
Reply to  Scoot Home

Oh, I see you’ve been to Toledo🤣

Chris Rush
20 days ago
Reply to  Dan Smith

Appreciate the link. I’m sure I saw it the first time around, but great to revisit it.

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