4 Glaring signs you need to take the freelance leap

I don’t think I chose the freelance life, I think the freelance life chose me.

While other kids were playing little league, I was trying to build a two story colonial house for my teddy bears out of logs, complete with shutters. That never really panned out so well (lack of nails maybe?!), but it taught me that I am most at home in the wild, without the road map laid out for me.

If something failed, I tried again. If people thought I was crazy, it didn’t faze me much. Naturally, upon entering the “normal” adult world of office jobs, I was more than a bit shocked.

I began to pursue freelance design on the side, with the intention of going in that direction one day. The more I did it, the closer that day seemed.

Along my six year journey through one full-time and two-part time jobs, the following signs led me to finally make the leap. If any of these resonate with you, the edge of the cliff might be closer than you think.

Start packing your parachute, and get ready to jump!

1) You’re cheating on your desk job

Have you ever snuck into the office bathroom to make a secret freelance call from the porcelin desk chair? Or used work time to send a quick reply or proof to a freelance client?

Yep, me too.

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I still needed my day job at that point, so it was a risky game to play. It can certainly lead to trouble, especially if you signed a non-compete agreement (I didn’t luckily).

It really is unfair to pursue your personal business on another company’s time and property. Eventually, you WILL get caught as you attempt to juggle both acts. That is NOT how you want to leave a company.

So, if you find yourself in a torrid affair with your freelance business while at your full time job, take it as a sign to make some changes!

2) You’re bad at normal tasks

In grade school I used to get in trouble for standing at my desk. Yes, standing there, next to the chair while the teacher lectured. “Tamara, sit down!” I hated sitting; I tried, but it was so unnatural for me.

As I got older and took my seat in office land, I realized I honestly struggled with administrative tasks that most people find “easy.”  I WANTED to do well, but I’d miss all these things that other people were seeing as an issue.

Example: in my designs, everything must be perfect. I measure my documents to the millimeter. But I’m totally undisturbed by that two day-old coffee cup sitting on top of that jumble of paper.

I would “get in trouble” for slip ups like this all the time in my normal jobs. It made me feel small, and stupid.

But then I realized I am neither. I am just different. I have different strengths. (And you do, too.)

I can design a mean logo and convince a client to pay me for it. I can stay dedicated to my goal long after others made excuses. Why should I keep putting myself into situations where my weaknesses are utilized and my strengths tamped down?

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If you feel as though you just don’t DO well in normal work environments despite your best intentions, maybe it’s because you DON’T! And that is OK! Take it as a sign to pursue something that makes you feel worthwhile every day.

3) Changes you’ve made are getting you no closer to your freelance goals

The final push I needed to go freelance came when I started a second, minimum-wage “part-time” job with 11-7, M-F hours. (I didn’t want to be “that person” who didn’t have a job.)

I could kiss my design business farewell. With hours like that, I wasn’t getting any closer to my ultimate goal. No time to accommodate clients during normal business hours before the shift, and no time after.

I sat there and I cried.

Then I took it as a sign. Now was the time. Now was when I would put 100% into my freelance business.

I quit and never looked back.

4) You honestly don’t want to live an “average” life

Some people work the same job their entire lives. We all know one or two. Twenty years in with the company, a nice pension, security, stability. That’s cool. If they are 100% genuinely happy with the life they live, more power to them! I however, am not this person.

For a creative like myself, I want to explore. I want to try new things. I want my potential to have no limits. I worked to design my entire life around those goals. I want to be able to travel, to meet so many people that come so uniquely into my life. I want everyday to be something different and I never want to stop learning.

I am willing to give up stability (but really, how safe is your job?) for that chance.

I’m not ashamed to say….I don’t want a fancy car in my two-car garage like I’m supposed to!

If you don’t want that either take that as a sign, it’s time to seriously start budgeting and planning out your freelance career.

“AVERAGE” is a choice. Choose more for yourself. If you can’t kick that desire out of your system, chances are you never will. Let it manifest and lead you to jump into your freelance career!

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Millo Articles by Tamara Morrison

Tamara is a freelance graphic designer and founder of Tamara Morrison Graphics, which specializes in providing small businesses with complete coordinated marketing and printing solutions. She also runs Tam's Tees, a custom T-shirt design shop. Read more about her quirky freelance life on her blog.
Read more from Tamara.

  1. Van Helen says:

    It’s the best profession, if you’re a hard worker, No doubt, keep it up. thank you so much !!!

  2. Md Razaul Karim says:

    Fantastic advice brother. I appreciate it.

  3. Radhika @ FulltimeNomad.com says:

    “It really is unfair to pursue your personal business on another company’s time and property. ” — Couldn’t agree more. And if you find yourself in that position, it’s time to make some sort of change for sure.

  4. Omar Faruk says:

    Nice collection buddy. Keep them coming :)Thanks for sharing

  5. Michael Cervantes says:

    Graphic Artist freelancer since 1989. I do not recommend it. You should be aware that you have freedom but it cost. You and your family pay a cost for your freedom. Not day for the money to came in, you will lost your credit, not insurances. If you have a family, think about it twice, life is not as romantic as we may see it.

  6. afzal hussain says:

    Well good and fun article but for new freelancer like me just dont know how to really achieve something. Hope to get any article about how to make a better living as a freelancer practically.

  7. Wow Tamara

    Reading your article and some of your blog
    Is just what I needed to hear, when I needed to hear it.
    (I too suck at math lol)
    Thank you, Thank you, Thank you so much.

    1. Tamara Morrison says:

      Derrick, Thank YOU, I love being able to inspire other people going after what I am, because there are many a day when that kind of inspiration keeps ME motivated and going as well! Best of luck!

  8. Diana Izquierdo says:

    I feel totally identified with what i read on the article.
    I’m currently working part time at a digital studio and working part time freelance.
    However, mi plan is to become full time freelance and travel as much as i can, because that’s my dream.
    Thanks for the article!!

    1. Tamara Morrison says:

      Diana, thanks for reading and best of luck!!

  9. Great article!

    1. Tamara Morrison says:

      Thanks Flavia!

  10. How refreshing! This article perfectly depicts my current situation! I love your candidness and how you challenge us to choose more for ourselves. I have always felt that I did not fit into the mold of a desk job environment.

    1. Tamara Morrison says:

      Thanks Kristin! Yeah, I certainly had many a day at my “normal” job where I really wondered what was WRONG with me and why I just was so bad at tasks most people did without thinking! But, then I did realize everyone doesn’t think the same, and some of the stuff I am good at they could NEVER do!

      What’s that Einstein quote, “Everybody is a genius. But if you judge a fish by its ability to climb a tree, it will live its whole life believing that it is stupid.”

      That pretty much sums it up. Find what you’re great at and lean that way and stop trying to pursue what you know isn’t right for you, because it will NEVER end well and the same mistakes will keep happening!


  11. #4 definitely resonates we me!! The freelance world is an opportunity for daily exploration and learning. And as the saying goes “with great risk comes great rewards”. Here here!!

    One of my friends was laid from her so called “safe job” after 21 years. I saw it coming for 2+ years yet she remained oblivious. By all accounts she’s been given a great opportunity. Then again you can’t want something more for someone than they want it for themselves…

    1. Tamara Morrison says:

      Barbara, is your friend freelancing currently since her job loss? Yes, you can’t make anyone have the drive to do it, my family suggested it several years ago, but I didn’t want to and “needed” to go through the traditional office experience to learn just how much I hated it! Then suddenly my drive was born from that negative experience.

      Freelancing is a roller coaster to say the least, one day your not sure whats going on, the next day you score a huge job, from someone you met painting a building on the sidewalk (true story). It’s not for the faint of heart, but everyday is something new, new people, new experiences.

      There is truly no way to more “fully” live, than to make each day nothing like the last. You just don’t get that in a company where you are in the same surroundings daily. Its like a package of Oreo cookies left open in the same cabinet too long, it just goes stale if it never moves! Thanks for your comment!

  12. I have to say this resonates with me on all levels. The difficulty for me being that I have 2 young children. It is very scary to make that leap and pay for the 2-car garage and after school programs. Budget should be my middle name, but is it so wrong to want to be a successful freelancer who can afford the 2-car garage? Thanks Tamara for this because it only supports my ultimate goal to be that crazy, creative mom in the neighborhood.

    1. Tamara Morrison says:

      Megan, I do hear you that having children certainly does complicate things, being that it DOES place more pressure on you to keep a higher income coming in. But NOTHING is impossible, and if you heart is set on doing this, you will find yourself doing what it takes to make it happen! Everyone deserves to find what makes every day worth living.

      Hopefully you do have a plan and great support system as I did (and still do!), and that helps a lot. Don’t get me wrong I still have my moments where I go “is this really going to work?!” but I have so many good things happen daily and I know I will make it work.

      Best of luck to you making the leap soon! You’ll be setting an awesome example for your children as well 😀

  13. Thanks for letting us in on what led to your moment of truth, Tamara. I’m planning to email my bosses on August 31st (Yikes… in just over a week), telling them that I’ll be moving on to go 100% freelance.

    Your article describes me perfectly, which I find comforting at this risky moment in my life.

    1. Tamara Morrison says:

      Hi Mathew, so glad my article helped you in feeling confident in your decision to leave your job!! You won’t regret it, even though it will have its difficult moments, there’s nothing I’d rather be doing!

      Sometimes you really need to just let life lead you where it will, and what FEELS right, and worry about the details later. Best of luck to you and let us know how it goes!!

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