Ryan (fake name) told me over Zoom that he was thinking about launching his own business, training dogs to walk on their front legs (fake business).

Me: Cool! When are you putting in your two weeks?

Ryan: Oh I wasn’t going to quit the day job. I just want this to be my side hustle until I can grow it more.

Me: Uh, but isn’t your day job also training dogs to walk on their front legs?

Ryan: Yes, but my boss is cool.

<red flags whipping up in my head>

Ryan: He saw some of my free YouTube videos and totally supports.

Me: He totally supports because that’s bringing business to him, since you work for him. You need to (1) check your employment contract for language around side gigs or competition and (2) talk to your boss about your plans.

Ryan: Ok yeah yeah thanks for the advice but I’m pretty sure I’ve got this.

<six months later, in which time Ryan did not talk to his boss but did announce the launch of his company>

Ryan: My boss is pissed.

Predictably so. I’ve seen this same pattern happen so many times, <insert joke about nickels and retirement>.

Margaret (fake name) got this same advice from me and said “It’s totally cool, our previous CEO knew about my side business and even encouraged me to do it.”

My dear Margaret, did you say “our previous CEO”? As in the one who is no longer your boss?

That’s like telling the cop who pulled you over for speeding that the last cop just let you go free.

Margaret did not talk to her new boss.

Margaret blasted her new business all over social media.

Margaret got fired.

Don’t be like Margaret.

Talk to your boss.

Say something like “I wanted to let you know about my plans to start a side business. I don’t anticipate that it’ll have any impact on my performance here. But I’ll be announcing it soon on social media and I don’t want that to take you by surprise.”

Be prepared with information about what your contract says regarding side work. Especially so if your side gig is similar to the work you perform in your day job.

You may have to speak to details of your plans, like your anticipated clientele, in order to illustrate how you aren’t creating a competing business.

But you don’t want to overindulge.

It’s a tricky conversation, for sure.

I’m not trying to fool you into thinking this conversation is going to be easy or clean.

It could get uncomfortable.

It could lead to putting some agreements in writing or, sorry about this, even more meetings.

Even if you follow my guidance here, there are no guarantees.

I *had* talked to my boss. I had my boss’s approval to work side gigs in writing. Girl, I had receipts!

And it still didn’t matter to HR, who told me I had two weeks to close my side business.

Their rationale: The topic I wanted to develop on the side – data visualization – could potentially become something the company wants to focus on also, at some point in the future, if they so decided one day. So, my side gig was considered competitive.

Hypothetically.

But, listen, bottom line is HR doesn’t care whether their logic is cohesive or fair. It doesn’t matter what your boss put into writing.

So why should you talk to your boss, if the conversation amounts to protection as fragile as an eggshell?

Because you’ll feel like you did it right. You’ll have gone about the process with your ethics and integrity intact, no matter the outcome.

On the other hand, don’t talk to your boss.

If you know your employer explicitly bans side gigs of any kind or you just have a boss that’s a little unhinged, don’t tell them about your plans.

You’ll be fired faster than you can tweet that you’re open for business.

Instead:

1. Build up the infrastructure of your business while you’re still employed.

2. Hoard your salary in a savings account.

3. Then quit your day job and launch your new website in the same day.