When We Encourage Our Kids to Be Entrepreneurial – and Then They Are

I wish my parents had inspired me to be more entrepreneurial and leap out into the abyss to make a real impact in the world.  Instead, they, like many parents of their generation, made sure I received a vocational education (I’m a CPA and Attorney) that would lead to a job right out of college.  This would lead to a stable career, minimal risk of lay off, or if I was laid-off I had skills that would hopefully make me re-employable.  They aspired for me to have a risk-free lifestyle.

So I went down that path, not knowing any better, and not willing to challenge my parents’ perspective.  Over the past 5-10 years, as my kids have gone from teenagers to college grads, I’ve taken a different parenting approach.  I’ve encouraged our kids to take risks, be entrepreneurial, don’t take the first and easy job, and more importantly, don’t worry what career path someone else has chosen for themselves.  We have told our kids not to worry what other’s think of their life and to blaze their own trail.  We only care that they are able to support themselves, make a contribution to their community, family, and friends, and are happy and fulfilled doing so.  My wife doesn’t always like me encouraging our kids to take these risks as she’s a little more risk-averse.  But she goes along for the ride.

While this topic is fodder for a much lengthier post that I’ll write later, it really brings me to my current predicament.  And I’m seeking the wisdom of the social media communtiy, including NGAGE Cafe and beyond for feedback.

You see, my daughter is a Registered Dietician and it turns out she’s actually been listening to me.  Instead of taking the easy route of working in a hospital or clinic, she’s decided to open her own practice specializing in food sensitivities and inflammation.  She has decided to become an entrepreneur.  In doing so, she’s smart enough to realize that at age 24 she doesn’t have all the answers to starting her own practice and running a business, so she is interviewing established coaches who have helped other R.D.s successfully start their own practice.  Here’s the rub.  These coaches charge A LOT OF MONEY and our daughter has now come to my wife and me asking for financial help.  A lot of financial help.

We will definitely provide the help, but we also believe the assistance should come with some obligation on her part.  We have a lot of ideas about what we think these obligations should be, but I’d like to hear from you.

How have you helped your children and what have you demanded of them in return?  What stipulations are put on the money you’ve loaned or advanced to them?  Is this just part of being a parent and they pay nothing back?  Do they pay it all back?  More importantly, what are the non-financial obligations imposed?

For instance, we already told her she has to live at home until her practice off the ground.  Should we treat this financial help as if we were investors in a business and ask for monthly financial statements, lead pipeline, metrics, etc . . . ?

Any and all wisdom of the crowds is welcome and appreciated.  I look forward to your thoughts.

Andrew J. Goldberg
Andrew J. Goldberg
Andrew Goldberg is the President of the Law Office of Andrew J. Goldberg. His clients come to him because they want Confidence and Clarity in the decisions they make and the direction they are heading. He loves working with entrepreneurs and using his 35 years of business experience to help them navigate the opportunities and risks of their entrepreneurial journey. He guides clients in thinking and viewing situations from new and different perspectives, and vigorously challenges them on their finances, marketing, production and manufacturing, HR, and more. And he does it with Passion, Energy, Knowledge, Experience and a large dose of Humor. Also a CPA, he is frequently involved in matters where legal, accounting and business issues intersect. He regularly counsels clients on business formations and corporate transactions, business succession planning, the accumulation and preservation of wealth for business owners, taxation, and general contract matters.


  1. I appreciate your reaching out for others wisdom on this question of parenting, offering financial assistance to our children, and how to stay aligned with your values, Andrew. I believed my most important message to my children was that they could be themselves and live true to their inclinations, preferences, beliefs, and inner wisdom. I gave birth to two old souls who seemed to know much more about living life than I did. They continue to be my greatest teachers. Creating structure, safety, and support for children to grow and become fully themselves with compassion, honesty, and integrity means modeling these values, living your truths. What does money mean to you? What does money mean to your children? What have you modeled that money means? What’s the investment you are inspired to make in your daughter? Money is just one of many resources. The quality of a person’s character endures over time, the quality of their relationships with others is another that’s important. Choices people make at critical junctures reveal values and commitments.

    We were fortunate to be able to invest in our son’s life, his recovery. Our son will likely not ever be able to “pay us back” with money. What he pays forward in his current brave actions and choices, his commitment to the lives of others, his work in the world inspires me every single day. I’d invest in him in a heartbeat. I believe in the loving, sensitive, intelligent, self-aware, compassionate, and wise person he is, in his ability to turn his life around and transform. I do not want payment. I want him to live a life of humility, love, and service to others, to know he matters, that his life is precious, that he is deeply loved, heard, seen, and that he has much to give in contribution to the quality of other people’s lives.

    What do you want your daughter to learn about herself, about life? Who is she becoming? Does she know and have an internal compass for her life journey? These are just some questions that I ask myself about my own children. I have a 21 year old son and a 24 year old daughter. We have lived through challenges.

  2. Andrew, for starters I am inclined to agree with your wife. There is something to be said for working a few years to gain maturity, learn what it is like in real practice, and build some financial strength. However, having said that I don’t think there is a “one size fits all” answer to your question. Situations vary but probably in most cases requiring a loan to be paid back establishes responsibility and emphasizes the reality of borrowing money in the real world. Another option is to help by co-signing or guaranteeing a loan from a traditional source such as a bank.

    • Ken, you and my wife must be having the proverbial “mind meld”. Her “conservative” nature and my “risky” nature tend to balance each other out. The irony is I encourage my kids to take many more risks than i am taking today (though situations are not nearly as comparable). I really like the idea of guaranteeing a loan from a bank. It also will help build her credit.

  3. Excellent points, Andrew. At key points in my 3 sons lives they have asked for a loan. Each drew up a simple promissory note. One son repaid with 10% interest- not expected on my part. He had borrowed years before and made regular payments. His partner has never forgotten the leg-up from a relatively small loan. Another younger son repaid several years later as he got on his feet with a start up business. Years later he is very successful.







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