Should you work after Retirement?

After selling our company and retiring at 50 years old, I didn’t work at all for about 4 years. We started a new life in a beach town, visited our kids often and traveled the world.

Inlet Beach Florida

After 4 years of retirement, I received a call from a good friend and past associate that was joining a startup company and they were looking for someone to build a software solution. He knew I was retired but asked if I would be interested in consulting with them to build the solution.

I said NoWhy would I leave retirement after working so hard for over 27 years and obtaining the ultimate goal of retiring early? He asked that I think about it for a few days and would call me back.

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I mulled it over for a few days. If I could dictate my terms, should I consider it? Would it impact my ability to travel freely, play golf several times a week, and do the things I love — fitness, boating and travel?

A few days later, he called back. I told him I loved being retired but I do miss the intellectual challenge of problem solving and the engineering challenge of developing software that can impact businesses in a positive way. I would consider it, but I had terms:

  1. I would have to be free to choose and hire the team that would build the software
  2. I don’t want to work full time, I prefer to work 4 hours or less per day
  3. I love to travel and must be free to do so (sometimes a 3 to 4 weeks at a time)
  4. If I begin working too much, we would have to hire backup help to reduce the workload
  5. My bill rate would have to be commensurate with my experience

To my surprise, he agreed to all my terms. It’s been a couple of years since I began. So how has it worked out? Incredibly well.

  • I built the team – True to his word, he allowed me to the build a talented software team. The business stakeholders and I provided the vision, I worked with designers and engineers to build great looking software that met the business need. The product has been in production now for over a year and has been a great financial investment for the company. It has already paid back the investment and is starting to become a profit center for them.
  • I work part-time – I’ve averaged about 4 to 5 hours a day of work. I normally start work early (around 7 a.m. — done by noon), that allows me to golf, boat and pursue other activities in the afternoon.
  • I still travel (a lot) – Since I’ve started just over 2 years ago, I’ve taken long vacations (sometimes for 4 weeks). I’ve visited 11 countries:
    1. Ireland
    2. Scotland
    3. Northern Ireland
    4. Batswana Africa
    5. Cuba
    6. Namibia Africa
    7. New Zealand
    8. South Africa
    9. Zimbabwe Africa
    10. Zambia Africa
    11. Australia
  • Hired Backup – Because I love to travel and the software has grown over the past 2 years, I needed backup. I hired a really talented engineer I’ve known for a long time to back me up and he has done a phenomenal job.
  • Financial Reward – Because of this consulting, we haven’t taken any money from our investment accounts since I started and we’ve added more money to my retirement coffers. We’ve also been able to contribute even more to charity, help my Mom financially in her final years of life. And best of all, we’ve been to spend freely on things we enjoy (like furnishing a new house, paying for all our travel, and buying a new car — all with cash).

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Looking back, this has been right for me. I’ve enjoyed the work, made a very nice living, and followed my passions. I never thought I would still be doing this 2 years later, but the software has impacted the business in such a positive way, they want me to keep working with them. As long as I can do this in my own terms, it works out nicely.


Steve and his wife built a software company, sold it and retired early. Steve enjoys blogging about lifestyle freedom, financial independence and technology. If you like this blog, subscribe here to get an email each time he posts.

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