Questions you should answer before leaving the family business

I can’t tell you how many times I hear frustrated family business members talking about making that final (and BIG) decision to leave the family business. I know firsthand what it feels like because I wrestled with the same decision for many years before calmly and peacefully reaching my decision.

That’s the important part. I always encourage those contemplating departure to make sure and explore every avenue of possibility before reaching their decision. Leaving the family business is a big decision. You want to make sure that you’ve done your due diligence in terms of your own thought process, as well as exploring others’ thought processes.

In most cases there isn’t a need for a quick decision.  In fact, take some time, give it some thought, and reach out for wise counsel from others who have been on a similar path. Uncle Walsh always said a fast decision is usually a bad decision. If you’d like to see a young man’s thought process, click here and watch the video of someone I coached during the process.

For the most part I’ve found that very few people regret the decision to leave the family business. Additionally, who says you can’t come back? I held that as a possibility in my mind. I figured if I ventured out and things didn’t go well, I would have felt better for having tried than the regret of never having tried at all. Doesn’t that sound like the old saying, “better to the loved and lost than never have loved at all?” “Better to venture out and fail than to never venture out all” -I absolutely believe that.

One of the most common reoccurring themes I hear with family business members in their mid-40s is the lingering question of “could I have done well out of my own?” It sounds a bit like a recent AARP poll of people’s top regrets at the end of their life. One is having “the courage to live a life true to myself, not the life others expected of me.”

I encourage clients to ponder a series of questions that will help them gain clarity during this very important process. Another thing I encourage folks to do is to be open and transparent with their family members about their own family business issues and disappointments and encourage them to go through your thought process with you.

My uncle and I had many conversations about areas of the business philosophy where we were not aligned. This allowed me to test my own resolve and conviction to my ideas and gauge his willingness or interest in changing directions. This was an important part of me getting to a peaceful and calm decision.

Leaving the family business will have an impact on you and those family members who remain. Sometimes when they ponder your exit, it gives them the impetus to make changes to improve the situation. Sometimes it doesn’t, but that’s okay, because at the end of the day, as a coach , what I want for you is to know that you gave it your best!

So set aside an hour and ponder the following questions. Being able to write your answers in a journal is a great way for you to be able to really explore your thinking, come back later and re-examine it. Make yourself write the answers to these questions.

◊Does the thought of leaving the family business excite you, scare you, frustrate you? As you look deeper what are your beliefs underlying those emotions?

◊Can you clearly articulate the number one reason why you want to leave?

◊Do you believe you’ve done everything in your power to bring forth needed change that would have you change your decision?

◊Is there anything else you could do? Are there any other resources you could bring to the table to try to bring an objective set of eyes to the situation?

◊Have you considered any sort of middle ground solution? Perhaps you could spend time getting retrained or retooled while still working in the family business. (I attended school at night and on weekends to get the necessary training to venture out to my next endeavor.)

◊If you fast-forward your life 20 years and look at the two roads; leaving the family business and not leaving the family business, what comes to mind? (Regardless of the amount of success have in your new endeavor?)

◊Do you have another job or profession you feel excited about going into? If not, have you considered spending more time contemplating that before you leave? Have you considered adjusting your own expectations so as to make your current situation more tolerable?

◊Have you solicited the input of:
      ◊Your family members?

      ◊Your significant other?

      ◊Your closest advisers outside the business?

◊Have you considered if you leave the business and it doesn’t go well, will you be okay with that? Would you ever consider coming back?


After you’ve answered all these questions, if you feel clear that it’s time to go then I encourage you to follow your heart. If you’re not 100% clear, I encourage you to give yourself time to get 100% clear or 100% committed to the decision. You have time.

My process for leaving my family business  was one of the most difficult and emotion filled decisions I ever made in my life. Now 15 years after that decision I still feel a great sense of pride for having the courage to venture out and still have no regrets.

The 9/11 crisis came shortly after I ventured out on my own. I knew failure was not an option. I have weathered the storm of one of the greatest economic recessions and still got two kids through college. Those challenges have been both daunting and extremely rewarding to have gone through. More than anything, going out on your own gives you the chance to put your money where your mouth is, put all of your hard work and focus on the line and really feel what it’s like to build something from the ground up.

There are no assurances within a new career change or new business endeavor. I do feel quite confident in saying if you stay miserable in your family business you will have squandered an opportunity to create a better life for yourself.

If I can help you in your process please lean on me. I’ll be glad to give you some time as my gift to you.


  • Posted by Coach Pete
  • Thursday, April 11th, 2013
  • Comments Off on Questions you should answer before leaving the family business