August 4, 2021

Challenges of the retiring entrepreneur

Eric Asbeck and Pixabay, Free for commercial use, No attribution required

Successful entrepreneurs are used to uncertainty and adjusting based on real-world experience.

Pick One” – an early lesson

One of the best pieces of advice I’ve ever gotten is there are always a lot of good choices, and then there’s the one you pick, commit to, and make great.”

Marissa Mayer, CEO, Yahoo!

Early in my career at Bell Lab, I had a great manager, Frank Field. Our team was creating new business opportunities for AT&T’s Business Unit.

We tried a few until we created something that ended up being a real hit. Along the way, we constructed a case study to showcase how it would work.

The team was debating how to construct a theoretical customer to use for the study.

When we reviewed our ideas with Frank, he instructed us to pick a real customer and use their exact situation. It was amazing. The debate about details faded away. There was no question about theoretical “what ifs.”

We constructed the case study and it helped us get the nod from the Business Unit executive to proceed. In the end, our idea proved to be quite successful and generated a good bit of business.

Since then, I’ve taken that lesson to heart. When I’m wondering which way to go or what to do, I turn to that simple advice: “Pick One.” Once that decision is clearly made, I can run with it.

Try it, you’ll be amazed how quickly it cuts through all the uncertainty.

Uncertainty is a part of life

There’s a lot of character development involved in learning to accept and take timely action on new information that contradicts your experience and beliefs.

What entrepreneurs do typically involves uncertainty. You move in a direction, creating something new, based on a set of assumptions.

Over time, you inevitably need to adjust based on real-world experience to achieve your goals. That involves being open to new information that contradicts your beliefs or assumptions.

You can use those same skills to find a way to retire that works for you.

Let’s look at some of the challenges to retirement from an entrepreneur’s perspective. Here are some challenges and some of the many questions about each of them.

Exit Plan

  • Are you planning for your future business exit?
  • Will (or can) you sell your business, have a succession plan where someone else takes it over (like a partner, professional manager, or your kids), or just close it?
  • If you sell it, what is (or will be) it’s value?
  • How will you value it and are you preparing for that now?


  • How are you putting aside savings for retirement, how much, and how often?
  • What’s your retirement savings and investment plan?
  • IMPORTANT: Inflation is a critical factor!


  • What are your plans for your retirement lifestyle and what kind of annual income will you need to support it?
  • People are healthier and living longer, so how long are you planning to be in retirement?
  • How do you plan to ensure you have adequate sustainable income over that period?
  • Have you given yourself an adequate cushion in case you are exceptionally long lived?

Guaranteed Income

  • Do you know how much your estimated Social Security payments will be?
  • Do you have any estimated pension payments?


  • What is your health insurance plan now and for retirement?
  • What about long-term care insurance?

Well, those are a lot of questions.

But what about answers?

Well, it depends… on you, your goals, and your specific situation

So many variables. Which way to go?

It goes back to “Pick One” – Clearly evaluate your options in a way that lets you see objectively how they’ll play out. Then you can pick wisely.

Discover a framework for evaluating your strategic options and making informed choices.

Join me on August 19 for my free masterclass, “How to Find Sustainable Retirement Cash Flow.”

Stay tuned for more about all this.

Until then, keep playing,


©2021 All Rights Reserved.

About the author 

Eric Asbeck

Hi, I’m Eric. Since I was young, I’ve been interested in having a business of my own but followed the more traditional corporate route. As a successful “intrapreneurial” executive at Bell Labs, AT&T, NCR, and Cisco Systems, I led teams to create new businesses, services, and products that won over $120M in new business. Later I left the corporate world and founded 2 new businesses of my own before realizing I could retire. I developed a very solid planning structure and a process that put my retirement finances in order (off-the-shelf methods didn’t cut it). I saw I had the means to retire with a modest but adequate lifestyle, so I did! I kept meeting other entrepreneurs who wanted to retire but were confused, afraid, maybe even panicking. I began working with them and improved my system. It’s been so rewarding to see them getting their own great results, turning survival and gloom into a clear plan to retire.

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