Problem: What If I'm Not As Successful As I Am Now?

For many business owners and people with long successful careers the prospect of leaving that world and "starting fresh" no matter what that is, can seem daunting.  The prospect of recreating the stability, psychological comfort, and other benefits of success can seem uncomfortable for some or down right frightening to others.  This is especially pertinent when some consider how they'll be perceived amongst friends, family, and peers.  This post explores this common challenge and describes several methods to overcome it.  There are lots of common stories people have so I've included a few examples below to help illustrate the challenge:

Example 1: Sally has worked hard in her CPA firm for over 30 years. She built it from the ground up in her rural community which has grown to a full fledged urban city. Her business has weathered the changes and economic ups and downs and now she's a thriving, well known business woman in her community and an active member in her local Rotary club. She's been planning her retirement for some time and has been mentoring someone to take over her firm and buy her out over a 5 year period.  As she approaches the time where she'll leave the business 100% she starts to really ponder what comes next, with all the associated excitement and feelings of a job well done.  She's started to think, though, that she'll be working from the ground up again in some way, that she'll have something to prove again, and that she'll be "watched" in some or another to see if this whole retirement thing lives up to the hype.  She knows many of these fears are unwarranted but she can't help ruminating on them a bit.

Example 2: Bob's been hard at work at his company for 25 years.  He's 55 now and doesn't feel "done" with work at all.  He's worked hard and made his way up to senior level status and is a respected technical advisor across the company. He really isn't thriving and stimulated anymore and now that his kids are on their own his mind has plenty of time to wander and think about what could be.  He finds a rekindled appreciation on the land and with his hands so he'd like to work with local farms and apply his technical skills to help them succeed and thrive.  He has no background in consulting or running a small business but he knows he can learn fast and fill in those blanks in no time.  He does, however, have a sinking feeling that he'll be holding himself to high standards and that he may have some expectations of success that could turn out to be detriments to the very thing he seeks.


  1. Reboot your baseline expectations. understand that many of the notions and feelings you have surrounding success are based on your own past experiences and also your perceptions of those around you.  Do deep work to rebaseline as you prepare for and start fresh.
  2. Express gratitude, in deep ways, often and regularly. Numerous studies have been done to show that, while appearing plenty cliché to many, expressing gratitude does work on us psychologically that helps to continuously refresh and rebaseline our perceptions and feelings about many things, but one in particular is our standards and high expectations.
  3. Consider a variety of comparisons to neutralize the "upward movement" of our expectations. If you're always striving for more, better, higher, especially when considering social comparisons, this can be an endless treadmill effect leading to less and less fulfilment. Keep this tendency in check, if you must, by comparing across a variety (although limited is best!) of cases of people you feel are in a more challenging place than you and perhaps some that you perceive are "better off" in some way.  Keeping this comparison neutral around you by considering downward and upward comparisons will help in the long run.