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Is Your Steady Paycheck Keeping You From Making The Jump? The Myth of Job Security.

By now, if you’ve read my about page or some of my first posts, you know that I recently quit my day job to go full-time into freelancing.

It was an amazing, freeing feeling. Having that conversation with my boss, telling my colleagues I’m moving onto better things, feeling in control of my destiny regardless of the uncertainty ahead.Yes, it’s scary. And even though I was immediately happy about my decision, there are those inevitable thoughts that go through your head, “Am I crazy?”, “What if this doesn’t work?”, “What will they think of me if I have to go back to working corporate sooner than later”.

All those thoughts revolve around one subject: Job Security.

I’ve gotten several emails from readers about their biggest struggle being just that. “I want to freelance full-time but I have bills to pay and so I can’t leave my steady job.”

Job security. The regular paycheck. Retirement. Being sure you can pay your bills every month and put food on the table.

But it’s just a myth.

A myth to keep us doing things we don’t love day in and day out.

We’ve all read stories online about the myth of job security. People getting fired, laid off, companies being sold, etc. But it’s one of those things you think only happens to others- until it happens to you.

This hit home recently.

I just found out the company that I quit from 5 months ago is moving their office to another country- and laid off everyone that couldn’t come along.


At first, I felt strange… oh, me being able to say that I quit to go out on my own isn’t as exciting anymore because I would have been forced to leave regardless.

But then I realized how amazing it really is. I took my career into my own hands, learned a valuable skill, and didn’t let some corporation decide my fate.

I got an email from a friend back in the states who’d just been laid off from the startup job she had been in the last 5 years. I remember her talking about the job over the years. And her reason for taking it and staying so long? Well it was a startup, that had a very good chance of selling quickly, which meant big stock payout for her when it did.

5 years later, it happens. But the stock payout? A couple thousand bucks.

Is a couple thousand bucks worth 5 years of your life? Not in my book.

Yes, we learn wonderful things in every job we have and I think every experience is a good one- somehow. She now has skills that will help her in finding a new job. But that’s called the rat race.

I asked a few friends to share their stories as well- because it happens to more people than you might realize:


Torie Mathis“During college I worked my way up at a small publishing house, eventually becoming the assistant publisher. I started designing on the side, to get more experience and to work on projects I wasn’t able to at work, stuff I really liked. The company was doing great in the soaring economy, focusing mainly on real estate agents as clients. As the real estate market collapsed so did this publisher, as each and every egg in their basket was connected to this one industry. The company went bankrupt and I had no “job”.

This took me from a nice little salary to a couple of small design jobs within months. I had just bought a house with my husband and knew it was time to see what I could do. That was 2007 and I have been running my business full time ever since then.

Looking back on this I see it is the desire to do what you love that brought me to where I am today.  Prior to the publishing house job I worked a full time corporate job, and made really great money, but it was not what I wanted. I left this corporate job, and the raise they tried to give me to stay to follow my heart. Crazypants. Looking back I see I made this leap twice, and both were the best decisions I have made. And it wasn’t always easy, sometimes you have to work hard and endure some struggle to get those things you really want.”

-Torie Mathis, Owner & Creative Director of Epic Creative Studio.

Gloria Owens“Six years ago I made a bold move: I left a long standing full-time job at a seemingly thriving graphic design studio to go freelance. I walked away from prestige, money and perceived security.  I had hit a glass ceiling and knew in my gut that it was time to put my faith in myself rather than someone else’s agenda.

Certainly as a freelancer you have to be willing to ride the ups and downs, deal with your own health insurance and wear many hats. It’s not for everyone. But I can say that for those with resiliency, creativity, self-discipline and trust that the net will appear. It continues to for me. And the irony is that the so-called security at my full-time job, was really an illusion; as the economy tanked, clients left and the agency fizzled and disbanded less than 2 years after I chose to leave. “

-Gloria Owens, Creative Director, Fish Cat Design

The moral of the story? There is no such thing as job security.

Now, I’m not telling you to go out and quit your job tomorrow.

However, do not waste your life in a job for just the paycheck, assuming it will always come.

Start preparing.

Learn useful skills that you are able to sell on your own.

Build a portfolio.

Get your name out there, and not just connected to your current job title.

Do these things to keep control of your own life & career.

Because job security isn’t all it’s cracked up to be.

Even if you think you’ll never want to say goodbye to the “steady” paycheck- prepare yourself for the inevitable regardless. It might just surpass your “steady” paycheck along the way!

And if you already want to leave, pick a date. Do everything in your power to get your business booming before that date. And then jump before you’re ready.

It’s amazing what will happen.

You’ve got skills. Sell them. Be free. Tweet that!

Checklist-CoversmallIf you’re ready to take the leap, you don’t want to miss this set of strategies that will keep you in the flow of “steady” income – that you make yourself! Go full-time with your freelancing by grabbing this FREE “Get Clients Fast” RUSH Checklist and start selling your skills, STAT.

Let me know in the comments. Is your steady paycheck keeping you from freelance freedom? Do you have a story about getting fired or laid off? We want to hear it!


Leah Kalamakis Leah Kalamakis is the founder of The Freelance To Freedom Project and a web designer/developer for brilliant entrepreneurs. When she’s not hanging out in the FTF Community, you can find her people watching on the streets of NYC. Come say hi on Twitter, Instagram, or Facebook.

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{ 13 comments… add one }
  • Awesome post 🙂 I officially went freelance at the beginning of this year (although I’d already had first clients during college, and the year has been hard.) Recently things have been looking up, and slowly it looks like I might actually be able to make a living off freelancing in the near future 🙂

    I work as a graphics and webdesigner for local clients and have recently started to push forward into the internet world, because I think I can find more fun and interesting clients online 🙂 I’ve also started a side-gig by selling wordpress templates on Etsy, which I’m enjoying immensely and which has started to bring in a reasonable amount of extra money. (
    And in my spare time… I draw monsters ( This actually took off better than expected.)

    Thank you for exposing the job security illusion, it’s something I know at heart, but the lure of a seemingly “secure” paycheck can be so hard to resist. I’m glad I’ve taken the leap to freelance and have stuck it through so far… hope things continue growing as they are right now, then I’m on my way to living my dream-life 🙂

    Thank you for being another source of inspiration for me… it’s always great to see others who are facing a relatable path!

    • Leah Kalamakis Leah

      Wow, thanks so much for sharing your story! Yes, there is no such thing as security in freelancing either- but it’s a lot more fun! I know it can be slow at first- it was for me too, but great job for putting out multiple streams of possible income. I love your monsters! What a great way of using a niche skill 🙂 And what people don’t realize is it’s ok to take on side-gigs here and there while things are growing. It’s easy to get stuck in the mindset that it’s a full-time corporate job or freelancing full-time- all or nothing. There are a lot of other options in between to help get you where you want to go. Thanks so much for sharing!

  • Everyone NEEDS to hear this that’s considering freelancing. I started my career as a freelancer, then thought a corporate job was what I was “supposed” to do after the kids were school aged, turned out that was a big HELL NO for me but felt stuck and hard to resist that steady paycheck, then I was laid off in 2010 and thank God! Thankfully that was the little push I needed to go back to freelance.

    • Leah Kalamakis Leah

      Yes! I think getting fired or laid of is actually such a great thing for people that are already thinking of escaping. When we are forced to make it work, we do, and we’re better off in the end! I’m so happy you got the push you needed and can now share your talents on your own terms. Thanks for sharing Amanda- I know so many people love to hear these stories!

  • This is so true and I don’t want to sound like a little old lady, but the fear of giving up job security gets worse as you get older. When you have a job or a significant other that keeps you “safe and secure” you tend to push back your freedom dreams. It’s a dangerous path. It’s true that if you don’t take the plunge one day you simply won’t do it. I’m fully aware of that but when is the right moment? Being impulsive might not be the best strategy. You can’t wait too long but you can’t jump too soon either. That’s where I’m stuck. I’m not sure if I have what it takes right this minute or if I should wait a little longer but waiting is also a mind trick.

  • Great article. I have several friends who have full-time office jobs that they hate, yet dream of doing other things with their life, but are unwilling to take any type of leap to see what else is out there. But maybe that way of life works for them? Feeling secure.

    One thing I’ve come to learn since turning freelance is that not everyone thinks like I do. Security and a set path makes most happy, but that way of life made me terribly unhappy. Every week is different for me now – I love it!

  • Hi Leah, great post and I can totally relate. I quit my job back in October and it has been a great learn experience. I worked there for 8 years and the last two I was miserable. I kept staying because of the paycheck…and then i switched the perspective. I looked at the amount of money and started thinking about ways I could make the same or more. Last month i matched my salary! This month i made more 🙂 it is a bit scary but so worth it. Thanks again for sharing ur story.

    • Leah Kalamakis Leah

      Oh I have many memories of being miserable, that’s for sure! Love that you were able to switch perspectives and congrats on matching and surpassing! Thanks so much for your comment.

  • Stephen James

    Reading this article is like coming full circle. You see I used to have my own freelance creative business up until the year 2000 and quit it all for a secure job.

    The corporate world is not the only employer. There are still truly secure jobs to be had although they may be few and far between these days. I now have a very secure job in Law enforcement. No chance of any layoffs or downsizing, it’s a job for life and there isn’t even any compulsory retirement age in my country. There will always be a need for law enforcement and the only way I could lose my job would be if I did something criminal to lose my job, which obviously I wouldn’t.

    I am a creative person who previously had my own successful freelance web development business up until the dot com crash around the turn of the millennium (I haven’t always worked in law enforcement!) Prior to that I worked in the telecommunications industry. Each time I had started to find career success in the private sector suddenly whatever it was I was doing would cease to be lucrative and I would lose my job. That’s when I made a deliberate decision to retrain for a secure job and chose law enforcement purely for the job security and rank based career progression it promises. I haven’t looked back.

    There is more to life than endlessly chasing the latest fad. There is a lot to be said for a secure paycheck.

    So whilst I agree with the “follow your dreams” philosophy for those in the private sector where there are few truly secure jobs, I also recommend that if you can find a truly secure job there is a lot to be said for that too.

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