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.



Problem: Overwhelmed by the options


In this post I'm addressing the problem of how too many options and choices are making transition decisions overwhelming.  This is resulting in delay, anxiety, and/or fear.  My examples are by no means comprehensive nor my suggested solutions.  Rather they are intended to provide some direction for understanding the problem and possible tactics for solutions.  I provide further resources below to learn more.

Example 1:

Having ran a successful general contractor business for 30 years, Jay seems to look at moving out of the business like this: Staying in the business seems simple, straightforward, obvious, with minimal risk.  Moving out of the business seems full of uncertainty, an overwhelming number of options, while many appear incredible and full of excitement, there are still many to choose from, and the risk of feeling like he made the wrong choice or really didn't get the most of out it, is making him avoid the decision altogether.

Example 2:

Mary had worked in her company for most of her 25 year working life career.  She had moved in and out of the company a few times but overall, Acme Corp. was HER company and the career she really see's herself as doing and being.  She's always been a strong saver and with her current 401k, Pension, and other personal investments, she and her partner can live even better than they do today.  Whenever she really sits down to plan for what she'll do with her time and energy (aside from the things she knows and love like her grandchildren, the local Rotary club, and friends) she really feels overwhelmed with the options available.  She's healthy and so is her husband, they could travel, by a small boutique store in their town and run that, start a non-profit working with educating children in developing countries, and a vast array of other options that really interest her.  When she gets the options on paper, she often feels demotivated, and the options seem less and less appealing the more she wrestles with them.


What Jay and Mary are dealing with is a common issue associated with both an abundance of available choices and also coupled with the switching from a constrained and structured lifestyle (from the schedule and rhythm associated with a business and long time career) over to the Freedoms associated with a new lifestyle in which they've moved from Freedom FROM work to Freedom TO Work. There are known psychological impacts that happen when people feel they have too many options available, too many choices to make, too many alternatives to consider, and too many criteria by which they're judging the choices.

Try the following remedies:

  1. Generalize the solutions to lower the overall number of solutions
  2. Consider MUST HAVE judgment criteria first and foremost and be very discerning on introducing any new considerations in your decisions.
  3. Decouple choices that seem like they rely on one another.
  4. Only consider 1 or 2 alternatives at a time
  5. Understand what choices are reversible and irreversible.  Understand some things can be changed and some choices you should make irreversible, so you don't look back.
  6. Don't look back on the decision, go all in.  If it isn't a "Hell Yes!" then say it's a no.

Book Resources that Can Help: