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Why Your Parents Will Never Be Happy That You’re An Entrepreneur

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Your version vs. theirs

Ok, that title is a little bit of a stretch and certainly a huge generalization. Of course, at some point in time your parents will probably be happy that you started your own business. I liken it to the way parents finally warm up to your spouse that they didn’t particularly care for in the beginning but have come to love…or at least accept. You know, the one you were madly in love with so they grinned and beared it while secretly thinking you could’ve made a better choice. Yeah, that’s them and your business.

I personally had a huge issue with this. I remember when I would call my parents every time I got a new client. “Guess what!” I would excitedly say. “I got a new client!!” or “Guys! They’re actually paying me to speak!” My parents, OF COURSE, were elated every time they heard this. “That’s our girl, full time job and managing two clients while landing speaking gigs.” They were always my first call after a business achievement, whether it was a raise or a new contract, and they always supported my enthusiasm.

So, naturally I couldn’t wait to call and tell them that I landed the client who would give me enough stability to step away from my full time job and focus on building my business. “This is going to be great,” I thought to myself. “They will be so excited to hear that I’m finally going to be able to pursue my entrepreneurial passion full time!” I was practically skipping as I called them. Here’s how it went down:

Me: “Guys, guess what? I got a new contract, and it’s enough money that I can step away from my job and focus on my business full time!!!!”

Other line: …. crickets…

Me: “Guys? Are you in a bad spot? Did you hear me?? I saaaaaaid I got a new contract and it gives me the stability to build my business full time!!!!….!!!!…!!!!”

Other line: “No, yeah, we heard you sweetie. That’s great! Another client! Go you! But, ummm, Kait, leaving your full time job? To pursue your business…full time? What about benefits? Retirement? Stability? You make good money now. Can’t you just kind of keep it up until, well, you know, you’re even more stable?”

Woooosh. I felt like someone knocked the air right out of me. I mean…what?!?! Didn’t they get it? I had killed myself for this moment. I had worked night and day at three different jobs for this moment. I stopped sleeping for this moment. I got a cheaper apartment in consideration of this moment. For goodness sakes, I stopped getting manicures and gave up cable tv so I could afford this moment!!!!!!! GUYS!!!!! Why aren’t you enjoying this moment as much as me??? 🙁

And that’s when I started talking to other entrepreneurs and found out a secret that only other entrepreneurs seemed to know…that parents are generally not as excited to hear that you started your own business as they were when they heard you got your first salaried job.


He just doesn't get it.


I have to admit, I found the whole thing shocking at first, but after a while, and after talking to many others who felt the same way when they made the entrepreneurial leap, I finally started to understand and make peace with it. Here’s why they feel this way:


1. It’s their job when we grow up to keep us safe.

That means from real danger and perceived danger. Real danger? Sticking your finger in a socket. Doing drugs. Driving like an idiot. Falling. Hurting yourself. Disease. Perceived danger? Broken hearts, hanging out with the wrong crowd, moving in with that guy.

Lack of steady income? While you, as an entrepreneur, have made peace with that perceived fear, they, as your parents, see it as very real. Guess what? They are your parents and have spent most of their lives keeping you safe. They can’t turn that off. So, obviously their natural instinct is to worry.


2. They come from a different place.

For any of your Rich Dad, Poor Dad readers, you know where I’m going with this. I didn’t have entrepreneurial parents and I don’t see that as a problem. My parents loved their jobs. They held steady careers as a police officer and a teacher and those careers allowed them to: spend tons of time with my brother and I as we grew up, have generous vacation time to take us places, consistently provide for us, pay our college funds, and retire in their 50s. Not too shabby. They were of a generation and a family who valued hard work and stability. They simply didn’t understand why I wanted to backflip off the cliff of financial security so I could “follow my dreams”. What kind of woo woo thing is that?

Lack of understanding breeds uncertainty. I don’t fault my parents for their lack of understanding, but I have stopped trying to get them to understand. It is not your job as an entrepreneur to make people understand (or approve) why you do what you do. It is your job to build a business that is rewarding to both yourself and your customers. Point blank.


3. …Or your parents came from the exact same place.

I have a good friend whose boyfriend’s parents own a small family business. The last thing in the world they want him to do is walk down that path. Long hours, debt, family feuding, maintaining books. They’ve been there and they want a better (more stable and less worrisome life) for their son. You can’t fault your parents for wanting that for you. That means they are good parents.


4. They certainly don’t want you to move back in with them.

Didn’t you get the memo when they took over your old room to expand the master bath after you left for college? Your parents are too busy traveling, joining wine clubs, and doing other empty-nester-like activities to start picking up after your broke self again.

Ok, so that last point was a bit of a joke…

In the end, I realized that my parents’ initial lack of enthusiasm was stemming from a place of love. That’s when I stopped being frustrated by their reaction and started to be thankful that they cared so deeply, and after that things seemed to ease up.

I also realized that I was bothered by the whole ordeal because I was secretly seeking their approval. Try as I may to deny it, it’s true. Like a parent’s job is to worry about their child, a child’s job is to please their parent. It’s nature. I started to accept that it wasn’t my job to obtain their approval, but rather to build a business that was so rewarding and successful that its results trumped any perceived approval I ever thought I needed. Since I started to operate in this manner, I’ve become a much happier person with an incredibly fulfilling and financially rewarding business. As for my parents? They couldn’t be prouder.

When you’re an entrepreneur, it’s a given that people just won’t “get it.” I’m curious to hear from those of you who have experienced this and what you learned from your experience. Please feel free to share below or shoot me a message.

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