Subscribe to Making Rain by Email

Spanish cellist and conductor Pablo Casals once said, “To retire is to die.”

It is with discomfort and considerable squirming that I report I am no longer an active entrepreneur. I am a retired entrepreneur. In effect, I have been retired since I quietly passed on my company to my employees at the end of 2015. Yes, I still write this as the Founder of a corporation, but the truth is I am no longer an active practitioner of our noble vocation.

The transition to being a non-owner has been such a difficult and uneasy process for me. I utterly haven’t wanted to let people know I’d decided to hang up my entrepreneurial spurs. I have been unwilling and unable to publicly and proactively declare my change in life direction–or to declare I am letting go an old life. (As Neil Sedaka puts it, “Breaking up is hard to do.”) For example, when an interviewer recently introduced me as CEO of my former firm on a podcast, I simply didn’t bother to correct the impression. I was a closeted retiree. Perhaps this column is my coming out, as it were.

As I look inside myself, I find I am reluctant to give up my professional identity publicly. I haven’t redefined myself yet in terms of the next phase of my life. I sit in the limbo of a vocational vacuum. Though I have told some friends, I have an interior dread that my acquaintances and long-time small business colleagues will not longer respect me or want to know me or to read my column.

I am suffering from a soul fear. My fear is of being seen as an an irrelevancy, an entrepreneur without portfolio, of becoming a crotchety retired guy fading into a curmudgeonly irrelevance.

In fact, I am still an impassioned student and acolyte of entrepreneurship. My belief in entrepreneurship has never been so strong and certain. I have just chosen to not practice it actively any more since last year for a variety of personal and financial reasons.

While my company grew healthily for a number of years–it was part of the Inc. 5000–and enjoyed substantial respect and reputation, the daily process of the entrepreneurial slog began to feel rote. I had accomplished what I personally wanted–to create a through-branded company based in truth, discreet efficacy, service, and profitability. A company based in practical love. A company I could live in. A company that made me and the people it touched better.

However, the truth I is my business attention was waning. And this waning began to show in the bottom line. Profitability was more than lagging. I wanted to do something else, even though I did not know what it was.

So I stopped.

My old company gave me the emeritus title of Chief Culture Officer and kept my phone extension in their system till this year, but in truth I had almost no contact and no duties or power with my former company.

I think the process of withdrawing from your own company is very similar to mourning a death. Note Elizabeth Kubler-Ross’ Five Stages of Grief in her seminal book Death and Dying:

  1. Denial
  2. Anger
  3. Bargaining
  4. Depression
  5. Acceptance

Additionally, there are moments when I feel an ego deflation. It’s a change to not be the big fish in my own small pond, to not be king of my own private Idaho. As Mel Brooks puts it, “It’s good to be king.”

My former company was my primary personal community and home to my spirit and lived beliefs. So for me and, I believe, most entrepreneurs, a business leave-taking is so much more than departing a job.

I think most folks believe the purpose of business is to make money, to amass wealth. But that has not been so for me. I believe and have found that business is a vehicle for meaning. Even without the financial rewards, the business journey is a reward in itself. It is a unique vehicle of calling, centering, and service, of finding integrity, freedom, personal dignity, and spiritual reality through an activity most would identify as quotidian and earthbound.

I intend to stay active in the local and national business community, still write this column, and perhaps start another venture eventually. I do want to continue to write and think about how business can be a conduit for meaning. Nevertheless, perhaps one truly needs to let go the known old to open up to the unknown new.

On his retirement from Cornell, Professor Scott Elledge said the following: “It is time I stepped aside for a less experienced, and less able man.” Thank you very much, Dr. Elledge.

25 Responses to “Why Leaving Your Business Is Like Mourning a Death”
  1. Tim, reading your blog is the highlight of my day, and perhaps the highlight of a month.

    I too have retired from the entrepreneurial journey, and share your feelings. By putting your experience into words you have helped me, and undoubtedly many others, to confront this sense of loss when one leaves one’s creation due to any number of circumstances. It is so very hard to confront one’s potential irrelevancy in a world which values youth, which values crazy-busy,’ which values ‘things have never been better.’

    Thank you, Tim, for allowing me, and perhaps many other readers, to feel that we are not alone.

  2. John Gaffigan says:

    Tim, as always, you are actively living a life that is true to yourself. I found this to be one of your most introspective columns, a clarion call to all Gen Xers who are likely harboring similar concerns. One overlooked asset of a newly retired exec is his/her ability to creatively apply their accumulated wisdom into whatever venture their free agent freedom can now take them.

    People recreate themselves in current society at a far greater pace than ever before. To the autodidacts (of which I know you to be one), the next phase of their lives has never afforded so much opportunity. One’s so-called relevancy can be defined as we deem fit…which is highly empowering. Applying wisdom to any new challenges they see fit to tackle will instill a profound sense of purpose.

    As Walter Gretzky famously counseled his son Wayne, “go to where the puck will be.” That zen-like advise only works for people who understand deeper context, those that have the wisdom to apply this whether on an ice rink or in life. Best wishes to you to find something that truly excites you in your next chapter!

  3. Karen Gottschalk says:

    Tim, you will always be an inspiration to me. Only able to work for you for a short time, it was nonetheless a pivotal career and personal experience for me and I’ve missed you ever since.

    Wishing you space now to find your next passion whatever that is but I do hope you stay connected to the world of business. Your voice is absolutely original and needs to be heard by the next gen.


  4. tim says:

    Thank you, Howard. So very much. This was a hard column to write, but I tried, nevertheless, to be scrupulously honest.


  5. Tim Askew Tim Askew says:

    Your great, Howard. What a very kind comment. This wasn’t an easy column to write. Thanks for your loyal readership.

    Warmest regards,


  6. Tim Askew Tim Askew says:

    Hey, John. I so appreciate your kind words. This is certainly one of my more personal columns and it means a lot to have your encouragement and support.


  7. Bob Koncelik says:


    I had no idea about this “retirement.” Guess you need a “closeted congratulations!”

    Maybe you can coach closet writers like me to release our work into the wild?

    Bob K.

  8. Theresa Boyce says:

    Well written as always. Whatever your current title(s), you are still you.

  9. Michael Drapkin says:

    Time for a new startup…..and wife

  10. Tim Askew Tim Askew says:

    Hey, Bob. Glad to coach you on writing any time. 🙂


  11. Tim Askew Tim Askew says:

    Thanks, Theresa.

    Warm regards,


  12. Tim Askew Tim Askew says:

    Maybe so, Michael. One day at a time. Thanks for reading.

    Warmest regards,


  13. Tim Askew Tim Askew says:

    Dear Karen,

    So glad you continue reading regularly. Your comment is wonderfully kind.

    All the best,


  14. Wendy Goulston says:

    Moving and brave, Tim. Thank you!

    Xo Wendy

  15. Marc Wager says:

    tim, i’m a fan! i’ve read most of your columns and really identified with many of them.

  16. Tim Askew Tim Askew says:

    Thank you for the very kind words, Wendy.



  17. Tim Askew Tim Askew says:

    Delighted you are a fan of Making Rain, Marc, and I am so pleased you have gleaned personal pleasure and wisdom from them. Please do keep reading. I’ll keep trying to have something new to say each week.


  18. Sandra Atenasio says:

    It is with deep regret that I read your column and with deep respect that you so eloquently (as always) were able to verbalize your status. Just by the sheer number of responses this column generated, tells you that you are deeply respected among entrepreneurs and the business community in general. Bravo and kudos with love for making the final cut (although awhile ago) to journey into new and unchartered waters. I can hardly wait to see what new and inventive ideas you will entertain us with. My only request is to keep up with the writing of this column, as I so enjoy its ability to keep me informed with the fast pace of the New York business scene while I work down here in the Palm Beach sun.

    I too am entertaining dropping the curtain on my small floral endeavor to return north to my children and grandchildren. I feel I have taken the shop to its limits here and am ready to start another small adventure up north. Us Askew’s never say die!! Keep me informed on any news.

  19. Tim Askew Tim Askew says:

    You bet, Sandy. I am deeply honored to read your eloquent encomium. I write this blog to help myself grow and understand as much as I want to communicate to my entrepreneurial brethren.

    Of course I intend to keep writing, though the direction may change as I explore new options. I just hope the community of readers will continue to follow whatever that new direction may be. But it will always be centered around practical ways to become whole and lead a fulfilling and useful life.

    With gratitude for your kind words.


  20. Robbie Briggs says:


    Great and poignant article. So often our identity is wrapped up more in what we do than who we are. You have just as much value now as you did two years ago, you just need to really know that. If you haven’t read the book or seen the newly released film, The Shack has had a meaningful impact on my life. I highly recommend it.

  21. Tim:
    One of your best, most personal columns ever. I relate to this a great deal. What if we define entrepreneurship as an interest or a passion or a style rather than a job or title? When I sold my startup and became an employee of a big company did I stop becoming an entrepreneur? When I was President of EO-NJ and not a business owner was I an Entrepreneur? We need to ask each other “Whats your passion?” Not “What do you do”. I continue to enjoy your writing

  22. Tim Askew Tim Askew says:

    Thanks, Robbie. So glad to hear from you.

    Warm regards,


  23. Tim Askew Tim Askew says:

    What a great compliment, Phil. This is certainly one of my most personall columns, you are quite right there. I also appreciate your comment because of your great success as an entrepreneur, as well as your writing skills. I’m honored that you relate to it.



  24. Kim Kaupe says:

    Hi Tim – What a great article albeit I’m sure extremely difficult to write. Sending you lots of kudos and support. Sometimes the best decisions in life are often the scariest and hardest. There is always light at the end of the tunnel!!

  25. Tim Askew Tim Askew says:

    You’re a peach, Kim. Hope all is going well with yourself and Zinepac.

    Thanks for reading and commenting.


Leave a Reply

Corporate Rain International on Facebook