Strike out on one’s own, or stick with the status quo? That was the question facing Cobus Visser, a South African and self-described mental strength sports coach and master firewalker. For a very long time he wasn’t sure.

He had moved on from the family business — going on what he called a “hero’s journey” — and discovered that his new path was not without peril. There was the time commitment, the financial hardship and the questions, from others and from within: Was this the right move? Always that. Always so much second-guessing.

In the end Visser concluded that the move had been well worth it — that life is too short not to take chances, not to pursue one’s dreams. (He also drew solace from the experiences of a man named Ali Mese, who had also transitioned out of his family business into content marketing.)

The point is that moving from the family business into private entrepreneurship is far different than any other career move. Emotions tend to enter into the equation — how could they not? — and flesh-and-blood relationships can be adversely affected.

For that and other reasons, it is essential to consider such a move carefully — to weigh all your options, seek advice, see the big picture and understand all the ramifications. It is particularly important not to act in haste, given the far-reaching implications of such a move.

A career coach named Pete Walsh writes that in his experience few people regret leaving the family business, as he himself did. His reasoning is much like that of Visser: Just as it’s better to have loved and lost than to never have loved at all, it is better to venture out and fail than to never venture out at all.

Walsh also mentions an AARP poll in which elderly respondents said that one of their great regrets late in life was not having “the courage to live a life true to myself” as opposed to one “others expected of me.”

But again, Walsh writes, this is a decision that needs to be carefully considered. He lists several questions, in fact, that those mulling such a move should ask themselves before making the leap:

  1. 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? This is something also mentioned by Stephanie Brun de Pontet and Chris Eckrich: Are you running away from something, or running toward something? If the former, it could be a recipe for disaster.
  2. Can you clearly articulate the No. 1 reason you want to leave? Closely tied to the first question, and something Brun de Pontet and Eckrich also discuss. Some of the common responses they see are, “He’s never gonna retire,” “I just want to get away from this conflict,” and “If only he would change.” They point out that in cases such as these, departure might not be the most advisable course — that, instead, it might be more prudent to air your grievances with the powers that be.
  3. Do you believe you’ve done everything in your power to bring forth needed change that would have changed your decision? Again, an offshoot of the previous question. In your present circumstances, you are dealing with family members, who at least in theory should be receptive to your thoughts and ideas. It’s a matter of sharing them.
  4. 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? Make a list of the pluses and minuses of such a move. Or better yet, use the Pugh Matrix Analysis, where the factors on your list are weighted.
  5. 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. Walsh, for instance, points out that he attended school at night and on weekends to prepare himself to venture out on his own.
  6. 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? One device that can be used to determine this is the Futures Wheel, a visual tool that enables you to see the positive and negative consequences of a decision. The desired change is written in the middle of the wheel, with second-, third- and fourth-level consequences of the decision added in the concentric circles around it.
  7. Do you have another job you feel excited about? 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? Most people like to believe they have a calling; determining what that might be is another story entirely. offers 20 ways that someone might reach a conclusion, at least one of which reflects the ideas mentioned earlier: Do not follow someone else’s dream.
  8. Have you solicited the input of family members, your significant other or closest advisers outside the business? Again, this is something Visser mentioned. As he was venturing out on his own, he very much needed the advice and support of his wife, especially as the money got tight in the early stages of the process and others (including his parents) questioned his direction.

Bottom line: This decision is not one to be taken lightly. It is not one to be made, Brun de Pontet and Eckrich point out, on a rainy day. And while emotion will certainly enter into it, it is best to be as logical and dispassionate as possible.