I Tried Working For Someone Part-Time — After 6 Years of Entrepreneurship

by Cole

A Look At Why It F*cking Sucked

I had a plan moving to Los Angeles, I promise. I had saved up about $6,000 with my real estate marketing business, knowing I would have to start over in LA. Got everything over here including two cats. Found an Airbnb. Then, an apartment. FANTASTIC. After that, my hope was that my coaching, courses, and content would keep me afloat while I built it out fully.

Well, it didn’t.

So as I watched my bank account dwindle, the hustler in me was activated. It’s been kind of exhilarating honestly. I did everything I teach my students and even found out some new tools along the way.


I was hit with the monster that plagues so many of us creatives & entrepreneurs — DOUBT. I doubted whether these side hustles would work. I felt like I couldn’t find one that was the perfect fit. I got scared..

So I began “job” hunting. Trying to convince myself that maybe it could work for me if I found the “right job”. Even though I have experience running my own team and a 6 figure business, maybe I can take a backseat and still be fulfilled. I’m okay with the thought as long as I’m able to spend my extra time building my own freshly started business in coaching etc.

I applied here and there, but even when employers contacted me, I had just enough hope left to not reply and accept the positions… Silly, I know.

Yet I still looked daily on Indeed & Facebook Jobs to see if anything stood out. Well, something stood out. Without getting into too much detail, I thought that maybe hopefully potentially, this PART-TIME position would allow me to be slightly creative about 8 hours a week at $25/hr.

One week into the position I sent an email to my “boss” to let him know the position was not a good fit for me.

As a serial entrepreneur and owner of my time, here’s why I think I hated it so much. This can be used as a tool in hiring creatives or motivation to stay focused on your mission as a creative.

Nitpicking Time

A huge plus of running your own business or surviving off of your art is that you don’t have someone micromanaging your time. This can also be a downfall if you aren’t quite ready to motivate yourself, but for me, it’s not just frustrating. It also drains all of the creative life out of me.

As someone who has hired people before and has also been worried about being able to pay them appropriately, I understand how nitpicking their hours is easy to do. But the bottom line is if you want to hire a creative person, you need to give them the space to do that. To be creative.

We are not just machines — we are people with real beating hearts and creativity that needs to be watered. And that’s all I have to say about that.

Relationship Building BS

At this point, I’ve been in sales jobs — including being a real estate agent — and networking groups etc. I know all the hoo blah of small talk relationship building and fake conversation. May sound a bit cynical here, but it makes me want to die inside. 😩

As soon as I heard this dude say — does that sound fair to you? I should have known how this would go. That is such a classic tactic, and I just.. can’t.

I wish I could put into words what you feel when you feel that someone is ingenuine. Or maybe it’s that there is a lack of care for you and an emphasis on just finding the right fit for the role that comes off so mechanical. Like I’m just a piece of the puzzle — not a human with dreams or goals.

Whatever it is — I can’t stand it, and most likely won’t ever be able to work with someone that makes me feel this way.

Lack of Connection

I’m diving deep here, but one large mistake I thought this particular employer made was to NOT invite me into the WHY of his business PERSONALLY. Yes, I read the website and thought there may be a connection. I’m sure I would have found it out eventually, but don’t you think this should be broken down upon hiring?

I understand how time-consuming and draining it can be to hire people, but this is such a big part of finding the right person. I need you to tell me WHY I’m supposed to give you 110%. Especially if I don’t know you.

What is your mission? What are your long-term goals?

I always wonder how it goes with the creators who already have a huge following. They post up WE’RE HIRING, and it’s kind of beautiful because SO many people already love them and their mission. Though I imagine there is so much to sift through, I feel like it’s a blessing to find your tribe in the first batch of hires.

Taking Up Mind Time

So I’m supposed to be working on this person’s business for 1 hour a day, BUT I’m also getting messages at all times, day and night. I’m making revisions. I’m having conversations about how to make them better. About how to grow.

At this point, you are literally taking up 4 hours of my mind time a day. As a creative, that’s incredibly damaging to my own goals & passions — especially if this is a part-time job. I mean JESUS.

As an employer, you have got to know this. You can’t take up this much mental and not pay for it.

In Conclusion:

I think what rubbed me the most wrong about this experience was the final word. This employer knew I had worked over 15 hours in 9 days of working with him. What he would do next was a test of character — in my opinion.

It’s time for payment. This motherf*cker.

He paid me for 6.75 hours of work.

Am I going to say anything? Nah. It’s not worth it to me. If this was my client, of course, I would make sure he paid. But this was up to his discretion.

And this my good friend, let me know that everything I was feeling was correct. His character is off.

I’d love to know how y’all feel about this.

After this experience, I think what I realized most was that these part-time jobs just aren’t for me. 100%.

Luckily, I found a few side hustles that have helped me while I grow out my own businesses. I did a whole piece on Rover here. UberEats has been super easy & a great find. I also use Thumbtack / Bark for my real estate photo gigs. More on all of those to come.

Benefits of Side Hustles

This may seem obvious at this point, but side hustles for the most part provide you with reasonable pay while you figure out how to monetize your business ideas without the mental space that many part-time job employers take up intentionally or not.

If you’re struggling with your part-time job and ready to take the leap into side hustling this thing — you got this. There are so many resources out there to help you succeed.

The bottom line is it’s okay if side hustles or self-employed is your thing. Whatever makes you happy folks. Keep grinding.

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