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Semi-Retired at 50, Traveling, and Enjoying Life. My Winter 2020 Check-In

  • December 12, 2019
  • 3.1K views
  • 8 minute read
  • Jeff Wiener
Early Retirement
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Just for fun, I added some travel pictures throughout this post.

October 17, 2019, marked the two-year anniversary since the sale of my business, and since I semi-retired at 50.

It took some time to get accustomed to no longer having the more-than-full-time responsibility of managing and growing a business. But now I’m very settled into a new life.

About 10 months after the business sale closed, around August 2018, I found myself looking for a new purpose in life. I had written my first book, done some public speaking, taken on a few clients, and was still doing some work for my old business. All in all, I was working close to 50 hours a week.

I felt the need to continue at the old pace I was working prior to the sale.

A few weeks before my family vacation in August 2018, I realized I was actually more stressed than before and not sleeping well. Consequently, it made me reconsider all the responsibilities I had taken on and, more importantly, whether I was enjoying everything I was doing.

When I returned from my vacation, I took a new perspective on life, which has served me reasonably well over the last year.

Having spent so many years building a business and dealing with the constant pressures of family and business life, I’ve found it somewhat challenging to just step off the rollercoaster.I do sometimes feel pangs of guilt that I’m not part of the worldwide rat race.

But I am busy.

Just at a completely different pace than I was last year, and definitely when I was running a business. 

I’ve come to appreciate that I don’t need to be super busy with work in order to be personally fulfilled. Yes, it’s been two years since I semi-retired at 50. But as of the last few weeks, I’m now moving into a different stage of life.

It’s now been six months since I last checked in, so, here’s my latest six-month semi-retirement update.

How to Thrive in Early Retirement

My wife initially asked me what I would do once I sold my business. After all, I didn’t have any formal hobbies like stamp collecting or woodworking, so I wasn’t sure how I would spend my time.

Semi Retire at 50
In Portugal

I now realize writing is my hobby.

Yes, I’m trying to turn my blog into a source of passive income, but it’s a hobby first and source of income second. I don’t have the pressure of having to build this blog into a cash flow machine.

Whether the blog makes an income or not is secondary to my personal fulfillment of writing. I have to remind myself of that from time to time. 

I also have too many other things going on.

I don’t think I will ever officially retire, otherwise, I might be retired and bored asking myself what I can do.

Managing my real estate and personal investment portfolio will always keep me somewhat busy, and I don’t have any plans for selling the real estate or handing off my investment portfolio to an investment advisor.

For starters, I thoroughly enjoy investing, and my real estate produces a very healthy cash flow.

If I sold the buildings, I would need to invest the cash, and I don’t think I’ll ever be able to produce the types of returns from an investment perspective that I currently get from real estate. So between my writing, real estate, investment portfolio, boards I am involved in, and consulting gigs, I am as busy as I want to be.

Between those things, I am fulfilled. It might sound busy, but it’s a completely different pace than even a few months ago.I’m not stressed about the feeling of not being stressed (if that makes sense). What I’m doing is my hobby. I plan to do this for many more years.

Is it Good to Retire Early? Live for the Now

Most importantly, I can travel.

morske orgulje zadar
Jeff in Zadar, Croatia at Morske Orgulje

I’ve known too many people who put off their life’s dreams until tomorrow.

For many, it ends up being too late.

They work until a health scare, at which point it’s too late to travel or try something meaningfully different. Worse, some succumb to their illness. That happened to my wife’s best friend, Joanne. She passed away from brain cancer a couple of years ago at the young age of 51. It was her passing that led me to realize I had to live life now, while I could.

As a result, I sold my business, and here I am today.

I find myself thinking quite regularly about life, my goals, and what I am trying to achieve. I’m 51 now, so I figure I have at least 30 good years left to live life to the fullest. I ask myself the following question:

“If today were the last day of my life, am I about to do what I want to do today?”

If the answer is no, then there needs to be a good reason to do it (doctor appointment, for example). Having said all that, the last six months since my last update have been busy.

Retire at 50 and Work Part-Time:  My Work Check-In

Writing a Blog During Retirement

From a work perspective, I’m really enjoying the diversity of challenges.

This blog is what keeps me busiest, and the last few months have been rather interesting.

I made the decision in September 2019 to grow the readership and number of hits to the site. In August, this blog had a domain authority of 19, and today it has a DA of 35. (You can read more about that here.)The number of web visits per day from Google has gone from 40 to now hitting 250, and the number of daily page views has gone from about 200 to over 1,000. I’m certainly not breaking any web records, but I’m learning a lot about SEO.

Jeff in Durbovnik
Jeff in Durbovnik

I also started monetizing this site a couple of months ago, but the ads are currently making less than $10 a day.

I don’t have any particular goals in mind for this website other than to keep writing, build the web traffic, and increase the revenue. I also hired a guest blogger who writes the occasional article.

Consulting Part-Time During Retirement?

Last year at this time, I had about six paying consulting clients.  I decided this past spring, when I went back to work full-time as interim president of the company I sold, that I wasn’t going to accept any additional paid consulting gigs.  My roster of paying clients is now down to one, and I’ve since removed the consulting tab from the top menu of this site.

Real Estate

My current real estate is doing well, and despite some efforts, I haven’t added any properties to my portfolio. I am looking to add one additional building, ideally one that fits the following criteria:

  •  low CAP rate
  •  between 10 to 30 units
  •  rents well below market

I plan to retrofit the units, raise the rents, and flip the property. I’m keeping an eye open, and I’ve toured a few properties but haven’t pulled the trigger just yet.

We’ve had a few vacancies in the last six months, which is unusual in the tight, low-vacancy Toronto market. As a result, we completely gutted the units and raised the rents. 

Manage Real Estate During Retirement
Apartment After Fall 2019 Renovation

In one case, the rent went from $925 a month to $1,600 a month (see picture at left) a $675 per month increase in profits. The renovations cost approximately $20,000.

I’ll recognize an approximate 35% IRR, a yearly increase of $8,100 in profit, and assuming a 3% CAP rate, a $270,000 increase in the value of the building just from that once vacancy alone.  And I’ve renovated a few apartments in the same manner in the last year.

I’m not going to get into detail about the calculations on the above information, but I did write a post on how to take advantage of a low CAP rate environment, which you can read here: Here’s How to Buy an Apartment Building and Make a Whopping 110% in Three Years.

Other Miscellaneous Work During Retirement

I’m still on the board of two companies. One is a not-for-profit that I will be stepping down from at the end of this year, and the other is my old company.

Starting this winter, I will be looking for another not-for-profit where I can volunteer and, hopefully, become a board member. Retire at 50

With regards to my old company, once I stepped down as interim president in June 2019, I was asked to let the new president manage the business without the encumbrances of the founder getting in the way. I have respected that wish, and other than the occasional board meeting and phone call, I now spend next to no time working for my old business.

Investment Portfolio

I’ll provide a short synopsis here, and shortly, I will do a much deeper dive into the portfolio, some of my holdings, and my investment philosophy.

So for 2019, year to date, I am up about 5.25% on the portfolio overall, meaning my net worth has increased by over 5%.

Considering my stock portfolio is only about 17% of my overall net worth, the small equity portion has done exceedingly well and has driven the bulk of the returns.

The balance of the portfolio is quite conservatively positioned at the moment, mostly in fixed income, bonds, and preferred shares.

I’m holding a large cash position, considering we’re at the tail end of a bull market, and I am holding on for a drawdown in the markets to deploy more cash into equities.

I spend at least 5 to 10 hours a week managing my investment portfolio. In fairness, that includes reading about economics [MC1] and not just about stocks.

The Personal Side:  Retire Early and Travel

On the personal side, my wife and I have done a considerable amount of traveling (hopefully you noticed some of the pictures scattered throughout this post).

That includes a family trip to Portugal, another to Croatia, and then, closer to home, multiple trips to Montreal, Ottawa, and even Halifax to visit my daughter in college.

We stayed at our cottage for many weeks this summer, and then we were in Florida for most of November.

I’m still going to the gym at least 5 to 6 days a week and am probably in the best shape of my life.

We have a busy winter planned, and that includes a trip to Southeast Asia, where we will visit Thailand, Singapore, Vietnam, Myanmar, Hong Kong, and Indonesia. I will report back in June 2020 with an update.

Does it Make Sense to Retire Early?

If you’re considering early retirement, I suggest you have some ideas of what you want to do once you stop working, otherwise, you might find yourself retired, and bored.  Hopefully, you’re not retired, bored, and out of money, otherwise, you might find yourself having to return to work.

Before I decided I wanted to retire early, I spent considerable time thinking about what I wanted to do during my days, and so far, as you have read above, I am quite fulfilled, and frankly, loving life.

I hope you have an excellent winter and holiday break.

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If you’re new to my blog, you might have missed one of my first posts:  My Journey Post Business Sale as I Sail Into a New Harbour. The Next Stage, Entrepreneur Semi-Retirement, and Life Post Business Sale

And this one: Why Do 80% of New Businesses Fail within 18 Months of Starting, and What Can You Do So That Your Business Isn’t One of the Casualties?

My goal is to help entrepreneurs scale their business, improve profitability, and then, use those profits to create massive wealth. Subscribe to my blog to receive my latest thought on scaling your business and creating wealth. Download my book and Amazon bestseller (number 1 in business, number 1 in non-fiction).  You can get your FREE copy here.

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Related Posts:

  • Semi-Retired at 50. An Entrepreneur's Life Post Business Sale. My…
  • My Three Year Semi-Retirement Winter 2021 Check-in
  • Entrepreneur Semi-Retirement. The Life of a Semi-Retired…
  • Entrepreneur Semi-Retirement. One-Year Check-In. Time Sure Goes Fast.
  • Entrepreneur Retirement - The Retired Life of a 50-Year Old Entrepreneur
  • My Journey Post Business Sale as I Sail Into a New Harbour. The…
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Jeff Wiener
Jeff Wiener

Jeff sold his company to private equity in 2017 and is now semi-retired. Jeff spends time traveling and with his family, writing this blog, managing his real estate portfolio of apartment buildings,  overseeing his investment portfolio, investigating angel investments, coaching other entrepreneurs, and managing his private equity holdings. Jeff is currently on a couple of boards, one for profit, the other not for profit, and now helps entrepreneurs grow their business, profits, and ultimately, create wealth.

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