The Right Way to Explain Your Freelancing Career to Your Dad

Earlier this week I read an article offering advice on how to explain your freelancing career to your dad. It’s something a lot of young people, including myself, struggle with. However after reading the article, my thoughts were less than flattering. Not only was it bad advice, it was a demonstration of what not to do if you’re serious about a freelance career. If you’re really interested in reading the article, I will link it at the bottom. For now, here’s what I consider the right way to explain your freelancing career to your dad (or mom, or whomever).

I should say right off the bat that I don’t mean to call out the author of the article, which is why I haven’t named the author; but when I read the article, the words that actually came out of my mouth were, “This is God awful.”  The basic thing that this article ignores is that it’s a hard sell because your dad is worried about you. I’m 28, my dad is 62. That means he grew up with the mindset that you get a job, stay there for 40 years and retire with a nice pension and great benefits. When our parents hear freelancing, they also hear lack of security. The thing you need to remember going into this is: Your parents care about you. They want the best for you. And they are worried about you.

With that in mind, here’s what I recommend. The author almost gets it right here: Frame your work the right way. You need to let your dad know that you’re serious about this, and that you’ve thought about all of the important things. What are you doing when you don’t have work? What are you doing about insurance? What about a 401K or other retirement plan? Have you considered taxes (which the author also mentions)? How will you support yourself? Be mature and prove to them that you’re serious. It will take time, but they will come around.

Listen to his advice. He’s not giving you advice because he thinks you’re stupid. Seriously consider it and show him. If you just write him off as someone who doesn’t know what he’s talking about, it speaks to your immaturity level. I can say that confidently because I’ve been there.

The other two pieces of advice could not be more wrong. The first is, “Use marketing buzzwords to confuse him.” This is really terrible advice. Are you trying to make your dad feel stupid? Do you talk to your clients that way too? Like I said before, the core reason there is friction when you mention Freelancing as a career is your parents worry about you. Confusing them isn’t going to make them feel any better. Try to explain what you do day-to-day, how you get clients, and where your money comes from in plain English.

The second is, “Create a fake plan that might accidentally become real.” Instead of making something up to sound mature and lying to your parents, actually make a plan, and don’t lie to your parents. If you don’t have at least a short term plan as a freelancer (how you’ll get clients, how much money you need to make, side projects and time management stuff) you are going to fail fast.

The last thing to realize is that being an adult is about being confident in your choices and being able to back them up. If you stick to your guns, your dad will at least respect your decision, even if it takes time. Lying to your dad and trying to confuse him won’t. I will say this: If my son wrote this article, I would feel stronger than ever that he shouldn’t be freelancing because he isn’t mature enough to run a business.

*Photo: My old man and me. Taken by Philip J. Casabona.

Here’s the article, if interested.

3 thoughts on “The Right Way to Explain Your Freelancing Career to Your Dad”

  1. I’d guess that the original author’s father disowned him or that they have some incresibly horrid relationship. You’re probably right that he treats clients the same way.

    All relationships – family, clients, coworkers, and good old friends need to be built on trust.

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