A Dream Job Should Still Feel Like Working


This is a donkey with wings. A beast of burden combined with a sense of dreaminess (or freakishness depending on how you look at it) with those unlikely, whimsical wings sprouting from its back. It’s a bank, too. If you look closely there’s a coin slot on that burdenless but still functional back. This winged donkey was an unusual gift, but sitting on my shelf, it’s become a perfectly-fitting reminder of how being a creative entrepreneur, as dreamy as that can be... is still working. You may be working for yourself, but you’re still a workhorse! As unglamorous as that title is, it’s true. But you are a workhorse with passion, vision, wings. And all your earning power, is not in someone else’s hands, but right there on your own back.*

*Not to be confused with “working on your back.”

After fourteen years of working in a small cool advertising agency in a dream job for someone else, and now two years of working in a small cool dream job I created for myself – I thought it would be interesting to do a little comparing, especially for those of you in either career position. What still feels like work? What feels like a burden? And what is still dreamy after all? 

Feels Like Work? Feels Like Dream?

Feels like work.
When you work for someone else typical burdens might be:
- punching the clock;
- compromising (or dumbing down) your creative vision; or
- just flat out personality conflicts, be it with your boss or client.

In my experience, though, all of those points above are cartoonish exaggerations, let’s be honest. I know everyone hasn’t gotten the chance to work for another creative visionary in an advertising firm. I have. So those typical (but probably simplified) complaints,  weren’t really the typical times I was like “ugh, back to the grind.” Maybe because I love the grind – the hard parts of rewarding work. 

For me, looking back, it was the in-between times that felt like a drag. Waiting for a client meeting to start, waiting for the mind-numbingly-slow elevator to just get to the next floor, waiting in the security line at the airport.  Waiting felt like work. Now that doesn’t mean it wasn’t fast paced. Oh man, was it fast paced. But when you are working within an organization, with more than just a couple people, you are going to have, hmmm, cracks.

On the flip-side, the super-extreme moments where I lost my own cool, in the heat of an intense decision, or series of hard weeks, or a series of hard decisions – now that felt like, well worry. I always worried after the fact that I said the wrong thing, let my emotions get the best of me, or over-stepped the line of what was professional into what was just considered artistic temperament, into what seemed like just plain crazy.

Feels like a dream.
Now, working for myself, I’ve been able to take so many of those “in-between” waiting times that had felt like a “drag,” but that are just the necessity of working within a team or a layered organization regardless of how fast-paced it may be, and compress them into a more condensed schedule of meetings and work, work and meetings. Now I only have to account for me, my biz partner (slash sister) and each specific client in our roster of dream clients – who must have specific times scheduled to get a piece of our carefully parcelled-out time.

All the cracks between are filled in.  

And now, here’s the rub, that space now feels so efficiently filled with dream clients and dream work, and me using my expertise in every spare moment – that oops, my obsessive compulsive dream of being as efficient as possible – oh boy, does that feel like work!

But that’s okay. Yeah, I miss the dreamy parts of working for someone else, and I hope the designers who work for Kathleen and I have dreamy parts of their day, and their purpose on our team, too. The irony is not lost on me that Kathleen and I are champions of the creative entrepreneur, yet we employ two creatives who work for our vision.

What are the dreamy bits I miss from the 9-to-5 of being a working creative in that team setting?
I don’t mean the “safe” bits, we all know what those are, health insurance, a paycheck, consistent wireless, I mean the feel-good stuff:
- I miss the culture
- I miss the immediacy of work-then-reward
- and frankly, I miss having a “ladder” to climb (not in a corporate icky way, just in, okay, here’s what needs to be done to push myself and this company forward, let’s get climbing!)

Why can’t I have those things in my new self-created dream job? And why can’t you?
Uh… you can. Your mood dictates the culture, and the people you let into your business (the clients you say “yes” to, do to… because it’s just you and them, so they better fit!) There is still a ladder, it’s just that you’re building it yourself. By hand. Sometimes with just bits of string and sticks and a will to not give up.  And if THAT doesn’t feel like working… and a dream… I don’t know what does.

Working for yourself? What feels like work, and what feels like a dream? Tell us on Facebook.

Braid Method Branding for Creatives ECourse

The Braid Method Branding ECourse is for creative entrepreneurs who are ready to support themselves financially with their business, create a blog or consistent online presence, and finally turn the work they’re already doing into a digital product, package, or offering for dream customers. This branding ecourse comes with 7 learning modules in a 300+ page digital download, a workbook with 20+ branding exercises and scripts, a quarterly masterclass, and an exclusive Facebook group so you can connect with us and other students.



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