Hey Elderly Aunt, how do I convince my parents that I have a plan to chase my dreams?

I’ve always wanted to open a new business. (I’m not going to specifically mention the kind of business in order to avoid someone swooping in and beating me to it.) I’ve got a plan and money saved and at least two potential investors. But at some point, I’m going to have to quit my current job to launch and make it work. I’ve told my parents about it, and they think I’d be silly and reckless to do that with COVID still going on. It’s true that beyond the research and the prep, I’ve got to take a leap of faith to pursue my dreams, right? What could I do or tell them to show them I’m not being reckless?

Let’s be clear about one thing right from the get-go, dear reader: Starting a new business—with or without parental approval—is always risky. Yes, your start-up has a chance to succeed, but it also has a chance to fail.  The bottom line is there’s no such thing as a sure thing. Period. Life is, will be, and always has been, about taking your best shot and then rolling with whatever happens next.

That being said, the Elderly Aunt encourages you not to let fear of failure drive your decision about whether or not to risk investing in yourself by opening your own business. Fear, in her opinion, is as life-withering a force as forces get.

It does seem to the Elderly Aunt that your decision is actually a two parter. There’s the obvious professional part, but there’s also a less obvious (but, perhaps, more long-term important) personal part. 

To her, it seems that you’ve already reached a professional decision. You’ve done your homework, you accept the risk and you are ready to trade in your current bill-paying trudge for the riskier and more satisfying adventure of starting your own business. Yet, you hesitate because your parents don’t approve.

If you’re not financially dependent in any way upon your parents and would not become so should your start-up fail, the decision is all yours. And if you’ve explained your business plans to them in some detail, and they still advise you to stick with a secure paycheck simply because it is secure, you still have the final say in your adult decisions. Is your parents’ disapproval of your well-considered dream a viable reason for abandoning it? 

Not for a second does the Elderly Aunt question that you love your parents and your parents love you. Instead, it seems to her that your parents are struggling to reconcile themselves to the reality that you, dear reader, are now an adult.  

In the Elderly Aunt’s opinion, the most selfless of parents teach their children well, then encourage them to fly free. While the most selfless of children recognize that stopping active parenting is arguably a parent’s biggest parenting challenge. With this in mind, dear reader, she suggests if you decide it’s your time to fly, then please make a real effort to fly kindly. Give your loving parents the help and support they need to get used to the idea that you, their loving child, has grown up. 

Speaking of flying…

For what it’s worth, The Elderly Aunt has made a life-long habit of embracing life as an excellent adventure that only she gets to have.  Being both irreligious and unconventional , she takes her procedural cues in life from irreligious and unconventional sources. Like song lyrics.

Way back in 1977, Texas singer/songwriter Townes Van Zandt had this to sing about the risky business of living:

To live is to fly
Low and high
So shake the dust off of your wings
And the sleep out of your eyes.

Amen, Townes! says the Elderly Aunt. Who is, as you may have guessed, a firm believer in keeping her own wings dust-free. 


The Elderly Aunt offers her thoughtful responses to your questions about this wild ride we call life on every other Monday.  And as a general disclaimer—to quote the elves from The Lord of the Rings — “… advice is a dangerous gift, even given from the wise to the wise.”

Got a question for the Elderly Aunt? Ask her on Facebook or email your question to [email protected] with the subject line “Elderly Aunt question.” (Just please don’t ask detailed financial questions). 

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