My WFH Art Studio-Turned-Office

What You Never Knew About The Freelance Life

Read This Before Going Solo

Over the course of nearly twenty years balancing freelance with both FT and PT employment, I’ve made a lot of notes about lessons learned. I’ve also eaten a lot of donuts, but that’s not the point.

These are the three most common, real, stark, and long-lasting challenges you should be aware of before jumping into the hardest work of your life.

At the end of the article I share a few practical and helpful ways to avoid getting lost in the very lonely world of Freelance or Independent work.

1. No one really cares for you.

You may have a friend or family member that cares about you, but you are your own HR representative, your own manager, your own colleague.

Your clients certainly care about your work, and the best clients will care about you, too. But no one is “checking in” on you. No one is stopping by your “office” just to see how you are. No one is expected to be present with you.

If you have a fever or a migraine, good luck calling yourself. The closest thing to a sick day you really have is an all-day Slack “appointment.” If you’re cheeky, you can add an appropriate emoji 🤒 that will likely go unseen. But it’s fun to pretend.

No one is stopping by your “office” just to see how you are. No one is expected to be present with you.

And take vacation or personal days, for example. The upside to your freelance business is that you get to set your own schedule because, in a way, the clients don’t care when you’re taking off and where you’re headed. Fun! But then again, they don’t care: the deadline is still the deadline and you are still contracted to get it done.

A real conversation I had this past year went like this. Me: So yeah, I’ll be heading up north in a few weeks, camping and hiking and generally unavailable without internet. Them: That’s awesome! Cool. Cool. So how will you dial into our call?

2. No one celebrates with you.

There are no high fives. There are no celebratory drinks. No one is here to share this joy with you. No one walks over to recall the inside joke about the first draft––the client said they wanted it that shape! It is you at your desk with your fingers on the keys. You reply all and sign off, “Cheers.”

This scenario will play out every day, on repeat, regardless of how many new clients you bring on board and regardless of the stellar projects you complete.

There are no high fives. There are no celebratory drinks. No one is here to share this joy with you.

Of course, we know that celebrations take on many shapes and vibes––they’re not reserved for end-of-work achievements: but be warned, you will find only silence for the smallest and most ordinary celebrations, too. There is no co-pilot on this flight. You’re flying solo and every win and smart decision will go unnoticed and uncelebrated.

The worst part is how quickly you will be tempted to believe that the lack of celebration is a reflection of who you are. A string of days without shared celebration can easily turn into nights of doubt and sadness: a depression for lack of shared joy.

3. No one champions you.

To champion someone in this context means to listen well, to give helpful feedback, and then provide real, meaningful encouragement that leads to holistic growth; there is no one “on your team” to push you forward.

Now, there are certainly folks who know you and love you, but are not connected to your business––but, you should understand that no mentor will be assigned to you. When you ask a question, it will go unanswered. Unless you begin that question with, “Hey Google,” in which case you should plan on the response: “I’m sorry, I can’t help with that yet.”

And, in contrast to the celebrations above, when you fail (and you will), there will be no one in your “office” to pick you up, look you in the eyes, and tell you to keep moving.

When you’re exhausted, you will get your own coffee.
When you hit a creative wall, you will take a walk by yourself.
When you feel overwhelmed, you will cry alone.

How to tip the scales and avoid a meltdown.

What do you do when the norm is that your freelance life, no matter the successes, will be largely absent of care, celebration, and a team who is championing you and your work?

Mostly, I have found some practices both small and fun, to help tip the scale towards good mental health and avoid a complete meltdown. Note: these are not failsafe or foolproof, but they are something.

When I land a big client, I buy a bottle of wine or gin and, over the next few weeks, I enjoy it with my wife. She may not know much about Adobe, but she can appreciate the hard work that goes into onboarding and sustaining new clients!

I begin and end each day with meditation, breath prayers, and/or yoga. Perspective is everything.

I don’t shame my use of Slack and Text Messaging––and in fact, I intentionally use them to help me laugh throughout the day. Bring on the gifs and memes!

I reach out to trusted voices in my life with direct asks about mentorship and/or advice.

When possible, I’ll bike into town and work from a local coffeeshop. I know this is not groundbreaking, especially for an extrovert like me, but there are folks who don’t love this idea. You know who you are, introverts. And it’s still a good idea to change up the scenery, talk to people, and be reminded that there are other creative things happening in the world, haha.

A lot of my “work” work overlaps with my love of art and photography––but it’s super important to pursue other hobbies and creative outlets throughout the day and week. My Instagram Stories will often chronicle these various shenanigans.

I find other Creatives to catch up with. No, they may not be part of my actual team or get the inside jokes, but they do understand the work at large. I encourage you to grab a beer, a coffee, or a walk with others to shoot the breeze.

I make it a habit to ask questions and, on occasion, write words. Like this. And to that end, I’d like to thank you for reading.

Have you been here? What’s your freelance story? How do you make it through tough days, weeks, or months? What lessons have you learned?

Let me know below!

Creative Agency Founder writing on ideation, art, and design. Photographer at

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