It’s now been 150 days since I “semi-retired,” and this is the first of my blog posts related to life post business exit.  I plan to do a formal check-in every six months (or so) and certainly sprinkle in anecdotes every-so-often throughout my other posts and material.


As entrepreneurs, we dream of what life would be like if we sold our business, and in turn, didn’t have to worry about money.  I reached that moment in October 2017, and from that day forward much has changed for me both personally and professionally.

For those of you who are wondering how I got to the stage of recognizing that I was ready to sell my business, I detailed that in a prior blog post. You can read that post here.

What Am I?  Retired, Semi-Retired?

I was caught off-guard in late December 2017, just a few days before I officially stepped down as President from the company I started in 1991. I was at the airport with my family headed to our home in Southwest Florida. We got to the Canada US border customs clearing, something we have done so many times over the years I’ve lost count, and the border guard asked the standard questions: “where are you going, how long will you be in the USA for”, and then asked the question “what do you do for a living?”

Sounds like a simple question.

Only this time it wasn’t.

I could have provided the same answer I’ve always provided, “I’m the President of a telecom company”, and in hindsight, I’m not sure why I didn’t.  For whatever reason, the question had me tripped up.

“I’m a, uh, uh.”  I looked at my family, and thought to myself, “what am I? What do I do?”

I blurted out “I’m semi-retired, and I am not sure exactly what I do for a living”.

The border guard gave me a strange look, handed me back my passport, and said “go-ahead.”

It was at that moment that I realized that I was unemployed, off the payroll, and for the first time in the last 30 years, didn’t have a job. This resulted in a conversation with my family about what I call myself.

Am I retired?

No. I’m not retired. I’m too young to be retired. And besides, I still plan on working and staying active. I have no intention of playing golf every day, at least not for many years.

Am I an entrepreneur?

Sure, but an entrepreneur of what?

I settled on the term “semi-retired.”  The conversation itself was innocent enough, but, started the thought process in my mind of trying to both put a label on what I was when people asked, and what I was going to do with the rest of my life.

The day I had dreamed of for the last 30 years had finally arrived.

Now, when people ask what I do for a living, I somewhat comfortably say “I’m semi-retired.”  I do of course tell them that I’m building a small business to help entrepreneurs reach their business and wealth goals, but, my plans now are very different from what they were 30 years ago. I have no intention of building an empire. Sure, 30 years ago I wanted to build an empire. Not anymore.

So, on that note, here’s what’s happened in the last 120-days, or, essentially the first 120-day entrepreneur semi-retirement schedule.

My Schedule is extremely flexible:  when I was President and sole owner of the company, my schedule was packed from 8:30 am to 5 pm with back-to-back client and staff meetings. I booked appointments on the 15-minute cycle, and between appointments addressed emails and phone calls. I worked from the office 4 of the 5 days a week and was on my email and phone constantly.  Now, my schedule is open, and very few of my meetings are in-person. They’re almost all by phone which allows me to work from anywhere. As a result, I am:

  • Less stressed, or, should I say, much more relaxed:  this is the most significant change.  Being an entrepreneur is a heck of a job. I was always working, and when I wasn’t working, my mind was still always thinking about how to move the business forward, the latest client issue, an internal HR problem, strategy … something.  I was never able to turn my mind off work. Now that I’ve relieved myself of that burden I find I am much more relaxed.
  • Sleeping Better: I’m sleeping better because I’m less stressed.

Travel and time away from the snow:  I’m not a big fan of winter and snow, and this year, I was at our home in Southwest Florida for 6 weeks between January and February.  I’ve enjoyed not having to deal with traffic and snow storms. In fact, I had an hour walk on the beach every day while I was in Florida.  My wife and I also took a trip to Boston and Halifax in March with my daughter to check-out a university for this September.

Work: I already mentioned that I’m not working full-time for the company I was President of, but, I still do work at least 10 hours a week in a consulting capacity, I spend some time working on my real estate (apartment buildings), I’ve looked at some VC (venture capital) and angel investment opportunities, and have also completed two books and designed and launched this website (you can download my first book, which is an Amazon best seller, for FREE, here).  I was working 60 to 70 hours a week before. Now I’m only working 35 to 40, but, it’s completely different. No stress and I have the flexibility to work from anywhere. The work is exciting and different because the challenge is new, but the most noticeable change is that I no longer manage teams of people.

Gym and morning routine:  before December 2017 I went to the gym 2, maybe 3 days a week. Now I go to the gym doing cardio and weights at least 6, sometimes 7 days a week. It’s part of my morning routine. I wake at 6 am (or so), read the newspaper online, and head to the gym for 7:15 am. It’s super quiet at that time, in fact, most mornings I’m the only person working out in the upstairs area. I’ve been to this gym at 5 pm, and it’s packed.  As a result of my new gym regimen, I feel fantastic.

Finances:  if you’ve read my book you know my investment philosophy and asset allocation strategy is to invest ⅓ of my assets in real estate, ⅓ in cash, and ⅓ in equity. With the sale of the majority share of my business and the extra cash from the sale, things have changed. I’ve spent some time looking at how to restructure my assets and figure out a new asset allocation strategy. I’m not completely there yet … it’s going to take many more months to figure this one out, and I’ll share some of those challenges with you.

So there you go. I definitely can’t say I’m fully retired, but, going from 60 or 70 hours a week down to 35 or 40 is my definition of semi-retired. I’m thoroughly enjoying the next stage of my work and life, but, I did spend countless hours over the last year planning what I would do if and when this day ever came.

If you want to download my first book, which was on the top charts on in both the Business (#1 overall) and non-fiction (#2 overall), you can download a free copy from my website here.

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