• Advice

Feedback from the Inferno: "My boss doesn't want me to have a side gig"

I moonlight as a freelancer and I know my boss will have a problem with it if he ever finds out. What should I do?

I have done freelance writing here and there for almost 10 years. I enjoy doing it, and I want to really get serious about it.

Here's my problem: I work full-time as an administrative assistant at a law firm, and my boss is not at all supportive of me doing anything that he thinks might take me away from my job. And let's be honest, he has a point - I do intend to leave when I've got my freelancing off the ground. For now, I need the money, and it's not a terrible gig, but it isn't where my heart is.

I already have one client that I got by word of mouth, and I know I need to advertise my services to gain more clients – which is scary enough, as I am an introvert – but I'm scared to put myself out there lest my boss discovers what I'm up to and uses it against me.

I would love just to be honest with him, as I have with my office manager, but past experiences have already taught me that's not an option; as examples, he fired another assistant partly because that assistant divulged that he was going to night school to become an EMT; he also was wary of me getting my CAP-OM certification until I described how it would benefit HIM.

I already dropped hints a long time ago that I really wanted to pursue writing, but that was dismissed and never referenced again.

Many others within the firm have ventures outside of the office, including my boss and all of the partners. But for them, the firm is an anchor. For me, it is a stepping stone.

My question is twofold: is there a way for me to advertise myself stealthily so that I can get clients without my current boss finding out? Or, in the event I just say screw it and put myself out there, how can I prepare to deal with the fallout?

I appreciate any help you can give - I am reaching out to you because I have heard you say to start freelancing part-time before jumping in with both feet, and I figured maybe you'd have some insight into a situation like mine.

I'm tired of holding back and missing out on clients and money because I'm afraid a simple Google search will cost me my job before I'm ready to leave.

A moonlighter on a mission


First of all, this is easily one of the best-written emails I've ever received. You clearly have the chops to make it on your own as a freelance writer.

Second, your boss is an absolute douche.

With that out of the way…

Finding Work

There are tons of ways to market yourself without actually exposing yourself. In nearly a decade of freelancing, roughly 80% of my work came from clients I never actually met.

Word of mouth, job boards, local meetups – they’re all great ways to find work when you’re first starting out. For your first few jobs, simply letting the world know (via twitter, facebook, etc.) you’re available for work is a great way to secure some warm leads.

However, that last bit of advice tickles your main issue…

On being googled

I almost always suggest a freelancer use their name as their business, and I think this should still be the case for you. I understand the fear of Googling – and it's a valid concern – but the idea of this boss owning your name online is utterly ridiculous. Plus, your freelance site doesn't need to be salesy or revealing. Giselle's illustration website is a great example of this.

To address this potential name issue, maybe you can focus on your first or last name to start. Remember, most of your potential clients will be directed to your website through you; very few clients will find you by googling "freelance writer" or whatever.

Preparing to go full-time (AKA dealing with the fallout)
Simply put, I recommend 3-6 months of savings for ALL your living expenses is set aside before you make the full-time freelancing leap.

I also recommend at least three positive client experiences before you make the plunge. Ideally, some of these clients will offer recurring work.

Other resources

Here are two articles I always recommend for this stuff:

How to Start Freelancing Without Quitting Your Job

An Experienced Freelancer’s Guide to Finding Clients

Also, if you ever want to use my Start Freelancing course to get a boost, I included a 75% off coupon in that link (FYI, I'll be adding a module for finding clients within the month).

Bryce Bladon runs Clients From Hell, hosts a popular podcast of the same name, and runs a monthly webinar specifically for freelancer FAQs.

Follow him on Twitter.
Or don’t. You do you.

Bryce Bladon Bryce Bladon runs Clients From Hell, hosts a popular podcast of the same name, and runs a monthly webinar specifically for freelancer FAQs.

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