My go to when friends (especially in my industry) ask how my business is going.

“It’s alright, but I won’t lie, most days I’m envious of where you are.”

It’s not entirely a lie as some days I do miss the days of a steady paycheck, less responsibility, and not having to make every decision. But more importantly, most people don’t want to hear about how awesome your life is because they usually hate where they are. So for you to say you’re envious of them, it not only does slates any jealously but makes them feel slightly grateful for the current position they have.

I need as many allies in my industry as I can get so I’m happy to put my ego aside and down play it if it prevents envy or jealousy.

Save cash.

Even if you’re killing it on paper, lack of cash flow will kill you.

If you can afford it and he’s valuable, give him a raise and more responsibility. I don’t know if I’d just give what he asks for because you set the standard that 10% every year its expected. Also, even though it’s likely not the case, but this employee will think you’ve been willingly underpaying them while they’ve been there until they had the balls to ask you.

If you want to keep them, meet them 50% to 75% of the way but add some additional responsibilities to it and track how well they handle those responsibilities. If they do great with it, awesome. You have a happy employee and greater bandwidth. If not, if the labor is as unskilled as you claimed, hire someone else and let them go.

As a former employee who got a raise after asking, I can tell you the honeymoon is short with granting the request in full. Immediately they’ll start wondering “should I have asked for more”, “why did it take me asking for my labor to be valued” and “well, every year I’m going to start asking”.

I don’t know your business, but if there is anyway to tie raises or bonus to performance, do it.

Perhaps I can be your cautionary tale as I was in a similar situation as you and chose to “pursue my passion” rather than taking over my dads business.

When I turned 24, my dad bought a mid level medical service business in an attempt to turn it around and make it profitable. I had just graduated college with a BA and marketing and had two entry level jobs lined up making ok money but I wasn’t excited about either of them. I was also deadset on becoming a musician (guitar player) where I made money here and there playing gigs around town and even had interest in purchasing some songs I wrote from a large music publisher.

After about 3 months into the venture, my dad realized how truly out of whack things were at the business he bought and he asked if I’d step in as an entry level tech at one of the satellite branches both to help out but also to be trusted eyes and ears of what was going on. I agreed, but in my head, this was merely a pit stop on my way to becoming “famous.”

After a full year of helping out, my dad sat me down and laid out a plan to profitability over the next 2-3 years, and how after that time, he’d be considering retiring and would want to hand it over to me. Great salary, a niche industry with little competition, and essentially, before the age of 30, I’d own a company likely worth 1-2 million dollars.

I f***ing turned it down.

Why? As cringy as it is to say, I’d been poisoned with the “follow your dreams” or “don’t do it if it doesn’t make you happy” pill. Like your YouTube videos, I loved playing music. And anything that took time away from that dream I looked at as an obstacle to be avoided. But here’s what that clouded thing caused me to miss…

1. The timing of opportunity. I could have always played guitar. You can always make YouTube videos. This was a once in a lifetime opportunity my dad was essentially handing me and I didn’t take it. Like you, at the time, I hated the business. But I never considered that I could step up to the plate to make it a business I like or at the very worst, still hate it and just sell it. This opportunity to learn, grow, and (the one I most regret) the opportunity to work and learn with your father is something hardly anyone will ever get. It’s valuable. So at the least, approach your decision on how to move forward with the respect for what you’re potentially walking away from in perspective.

2. Every gig you’ll ever have will have an element of suck to it. “Loving what you do” was a detrimental mentality for me in my early 20s. As soon as things started to go south at any job I was at, I immediately just decided “I don’t like this anymore. Time to look for another route”. And that’s not to say you should stay in a toxic situation, but there was no self reflection on my end about if there was anything I could be doing to improve the situation. I was like a narcissistic employee. The job existed to meet my wants and needs and as soon as it didn’t, it was t my fault, it was the crappy jobs fault. Spoiler alert, I never even came close to cracking 6 figures when I was in this mode.

3. This last one is more just a relationship with your father concern. I noticed in your message that you said you don’t want to tell him about YouTube because you’re afraid he won’t understand it. The one thing I would say is you need to get real honest real fast with pops before anything you do will influence how he’s going to run the business. He likely has a ton of money and plans tied up in the future of that business and it wouldn’t be fair for you to allow him to make plans to turn it over to someone who a) doesn’t want it and b) has one foot out the door already and who will likely run the thing into the ground not being focused on it. I told my dad about my goal of being a musician and I was a bit embarrassed as well. But I told him, “I’d rather be embarrass my honest with you and respect your investment rather than lie to you to avoid embarrassment and potentially let what you’ve built crumble on that lie”. Talk to your dad and get super transparent. He might laugh. He might not get it. He might even think you’re being a complete idiot. But he can’t say you aren’t being an adult about being upfront with him.

Long story short, I regret not doing it. Even if only for the experience of running a business with my dad, it was an opportunity I’ll never get again. It’s been 20 years, and I still play guitar, write songs, and perform nearly every week, but that one opportunity is gone for good.