“Pick and Run” – Choose, Commit, and Make It Great

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,


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Categorized as Articles

By Eric Asbeck

Since I was young, I’ve wanted to have my own business. I thought it was my best way to achieve financial freedom and do my own thing. I found my initial success through the more traditional corporate route, focusing on business strategy and creating new product and services. 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. Then I left corporate and founded 2 new businesses of my own. Over the years, along with learning about business startups, I kept searching for a reliable way to have money freedom. I developed a planning structure and process that showed me I could retire, be relaxed about the money and not worry where it’s coming from, and do what I want when I want… So I did! It’s in my nature to share what I’ve learned and help people, so I began working with other entrepreneurs who also wanted financial freedom but were confused, afraid, maybe even panicking. It’s been so rewarding to see them getting their own great results, turning survival and gloom into a clear action plan and checklist for money freedom.