Jane’s Journal

Thought I’d share a journal entry today (with permission). It’s from a woman, Jane, in her 60’s who started a business early in her life and has been working it ever since.

See how this lands for you:


Today, I found myself standing in front of the mirror, questioning what comes next. I’ve spent so much of my life, almost 40 years, building my business, a company I’m truly proud of. But now, I’m at that point where I need to think about what I want for myself beyond my business. 

I feel like I’m standing at a crossroads, with one foot in my past as a successful entrepreneur, and the other in my future. The future feels both exciting and terrifying. There’s a strange emptiness, a void filled with uncertainty and worry. I ask myself – have I spent so much time on my business that I’ve missed out on other fulfilling experiences? Will the rest of my life be as meaningful as the years I spent building my company? 

If I’m honest, there’s a fear within me – of the unknown, wasted time and lack of direction. The thought that I may not be able to make a significant difference in my own or others’ lives in my remaining years scares me. The legacy I leave behind, is it only about my business? 

I can’t help but fantasize about a life where I’ve managed to find a new purpose, something that aligns with my joys and passions, something beyond just the world of business. How wonderful it would be to wake up each morning, excited about the day ahead, not with the stress of board meetings and sales targets, but with the thrill of embracing something I love. 

The idea of carving out a meaningful, joyful life in these golden years seems so distant, but I can’t deny it’s a dream worth chasing. I can see myself in this dream, contributing, learning, growing, and more importantly, living, not just existing. 

Oh, what a life that would be!


When she shared this with me, I felt like it could have been my journal entry. I wasn’t straddling business ownership and the future; instead, I had been lying in a hospital bed with a potentially fatal condition and wondering what the future would be. Is the business I had what I wanted for the rest of my life? Is this the legacy I wanted to leave? I just kept thinking, “There has to be more!”

The questions and fears were the same for both me and Jane, though. And as we reach the age of 59 and beyond, the questions are more acute — we’ve lived most of our lives already and we have another 20 years ahead (maybe, we hope.)

Statistics say the average life expectancy is 79. We all know people who’ve lived longer, and some who haven’t even reached 60. It’s not the number that’s as important as recognizing we have a lot less time ahead of us than what we’ve already lived.

When you find yourself standing in front of the mirror asking these questions, the catalyst may be:

  • Realization that you have less time ahead than what you’ve already lived
  • Death of a loved one
  • Separation or divorce
  • Disease or disability
  • Some other major life event


So now what?

Do you want to keep your business going, working as you always have?

Are you looking for fulfillment and purpose by getting involved in a cause you hold close to your heart?

Do you want to mentor young businesswomen as they begin their entrepreneurial adventure?

Do you want to live a life of leisure, having no specific plans so you can indulge in spontaneous pleasures?

There is no right or wrong, good, or bad, to the choice you make for your encore. What’s important is that you be able to answer the question about what is going to bring you joy for whatever years you have left. Exploring the possibilities is a fun adventure in itself — imagine all the opportunities and choices open to you!

Can you put yourself in your encore where you’re contributing, learning, growing, and more importantly, living?

Like Jane said, “Oh, what a life that would be!”

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