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Retirement Takes an Entrepreneurial Lifestyle

By Lynnelle Wilson, Founder of BOLD–WOMEN Over 60

Here’s a thought for you to consider: Retirement is an entrepreneurial feat.

When you have a job, even a high-C-level job, you’re an employee. Unless you’re an entrepreneur, your fulfilling career requires little from you in the areas of risk, commitment, and faith. Think about it. When you’re an employee, there are relatively few variables you have to evaluate day-to-day. Most of your day is filled with “givens“…

  • When to get up
  • When to go to bed
  • Where to go
  • Where to sit when you get there
  • Who to associate with and when
  • When you take time for yourSELF (Whaaaaat’s that!?!?)

Even if you LOVED your job, you were still following an established map; someone else setting the direction, providing certainty, and security.

When You Retire, You Need a New Map

When you leave work, you have an ending point. You may have a financial starting point. You probably also have a few destinations in mind (id: bucket list “to-do” items).

But I’ll bet you don’t think about all the “givens” that become choices; choices that depend on your map.

When your retirement “honeymoon” – what I call “Phase 1” – wears off, it becomes crystal clear that you need a new “map.” (I talk about Phase 1 of the 6 Phases in this YouTube video, and all 6 Phases in my eBook)

How will you live your life, day-to-day, year-after-year as an engaged, vibrant individual? Creating that map is up to you.

Like an entrepreneur birthing and growing a thriving business – when you retire, YOU are an entrepreneur, birthing and growing a new life where YOU can thrive.

What is an Entrepreneurial Lifestyle?

It’s a mindset. PERIOD.

Even though it’s almost 6 years old, this article by Executive Coach Danny Creed explains it so well. He writes this for someone building a business or a career, not a life. Still, read it and replace the words “work” “payroll” and “income” with “guarantee” – you’ll get it.

If you’re a woman who has left a long career and is embarking on a new beginning, this perspective will encourage you as you begin to (re)build your life, post-career.


My takeaways:

Going from employee of a business to entrepreneur of your life requires a mind shift; a paradigm shift. You have to change the way you think about:

1. Sacrifice

When you retire, the people, places, and things in your life are there because of who you were and the map you followed over the last 5, 6+ decades. Everyone and everything are comfortable with the map and with the you who followed that map. Change can be scary for you, but it can be a downright threat to others close to you. As you begin to think and do things differently, be prepared for pushback, communicate well, and set boundaries.

2. Faith

As mentioned above, everyone in your life may not have the same motivation and confidence in your new journey. You have to have “unfailing belief in yourself” even when it feels like no one else believes in you and you’re totally alone. (Tip: You’re not alone. So very many women experience this, including yours truly. Still, it’s not fun.)

3. Persistence

The world isn’t fair. The world doesn’t own anything to anyone. Intention is good, but it’s only the tip of the TIPPY-TOP of the iceberg. (Hat-tip to Barbara Sher and Bari Baumgardner)

4. Risk

Living authentically, on your terms is risky, as discussed specifically, in #1 above. You have to be prepared for consequences, expected and otherwise. Think long and hard about potential consequences. Those that you are not willing to take on will require you to compromises that will be required of you in that event.

5. Commitment

You have to be committed to all of it; the sacrifice, the faith, & persistence. Change will be difficult for some to accept. To be fully committed to your dream, value(s), purpose, or committed to finding any or all of these, you have to be willing to:

  • Disappoint those you love.
  • Face criticism and insults from all fronts.
  • Allow people to leave your circle.

Retirement Ain’t for Sissies

Yay you, if you’re one of the fortunate ones who sailed smoothly from a fulfilling career to a fulfilling, engaged, vibrant next phase of life. Many of us, however, have to make it happen. It’s time to cowgirl up.

All it takes is a bit of Gumption & Soul.

Lynnelle Wilson is founder, mentor & chief cheerleader of the BOLD-Women community. After retiring from a successful career, she discovered how much more than a paycheck you leave behind. Now, she’s on a mission to help women redefine their “retirement” paradigm. Rather than a time to slow down and kick back, BOLD-Women seek a mentally, physically, socially, and spiritually active life – post-career. BOLD-Women is a resource and a community for post-career women who are transitioning from a life focused on conventional success to one prioritizing authenticity, personal growth, and exploration. 




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Sheila Hamwey
Sheila Hamwey
1 year ago

What a great article. It takes commitment to move forward happily. Love “cowgirl up”. When I retired, the book, “A Year by the Sea: Thoughts of an Unfinished Woman” by Joan Anderson was an inspiration.

When we retire, everyday is Saturday, and we earned it.

1 year ago

And sometimes “retirement “ occurs due to health, too young, and yes, “cowgirl up” is a great adventurous thought, cuz doesn’t it all begin with thought, to envision! Women reinvent ourselves over and over again in our journeys, it’s not our “first rodeo”! Thnx

Amy Lampert
1 year ago

I LOVE this piece, Lynnelle! As a retiree who started working at her “why” at age 6–an encore career, if you will–my life is the most productive and affirming as it’s even been! Thanks for the nudge for us all to take the risk!!
AmyLampert, WomensWorth

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