4 Tips For An Easier Transition To Full-Time Freelancer

This is a guest post from my (super inspiring) friend Jeffrey who recently quit his day job to become a full-time freelancer. You can check out his writer site to find his work all over the web.

Freelancing full-time means no pay unless you find your work, constantly dealing with clients’ needs, and increased expenses for health care and taxes, too. Terrifying, right?

I’m not going to tell you full-time freelancing is easy or always incredibly lucrative from the get-go, but I can tell you that it’s been incredibly rewarding and well worth the challenges.

Here are my best tips for leaving your job and turning your side-gig into a freelance career.


Know Why You Want It

Earlier this year, I achieved my dream of quitting my job and going freelance full-time. I’ve always valued flexibility and my free time over the money or stability of a job, and this helped me find the motivation to leave my job as soon as I could afford to.

My major reasons for freelancing: working on my terms with the freedom to live and travel before retirement, wherever and whenever I want. For example, I just camped for 3 days without turning on my cell phone or computer even once. Now I’m writing this post in Colorado where I’ll be for 2 weeks without having to worry about conserving vacation days at a desk job.

You need to think about what gets you motivated and excited. Just being sick of your job won’t cut it. Maybe it’s being your own boss and only wanting to work on things you’re excited about. Or do you want to work at home because you have kids? Decide your own reasons, and you’ll be much more likely to succeed as a freelancer.


Make Saving Your #1 Priority Early-On

Having savings as a cushion is, without a doubt, the best decision I made prior to quitting my job. If you’re planning to make freelancing your primary income, I’d definitely recommend planning and saving as far ahead as possible.

I paid off $6,000 in student debt by December 2011 and saved another $7,000, all in less than a year and before I quit my job in May 2012. This would provide about 6 months of living expenses for me while covering gaps in payment from my freelance work.

Here’s my nearly foolproof plan I used for hitting a goal like this:

  • Set a Concrete Goal. If your goal is to quit your job and freelance full-time, set a target number for savings then set a target date to quit your job. Be serious about committing to quit your job by then.
  • Cut spending. While I don’t live a ridiculously-frugal life, I get by on a reasonable budget each month. I lived in the cheapest apartment out of all my friends, never ate out for lunch at work, and I own a bike instead of a car. You don’t have to do these exact things, but the lower your monthly expenses, the better. This will help after you make the leap, too.
  • Increase income. Not only is starting out freelancing part-time necessary before trying to make it a full-time option, but freelancing will increase your income and help reach your savings goal faster.
  • Automate. Making the goal automatic was a huge factor towards making this a success. I saved 50% (about $700) of my paycheck every two weeks by setting up an automatic transfer to a savings account. Don’t rely on memory, set up a system.


Line Up Just Enough Freelance Work

Instead of just quitting your job and attempting to live off zero income until you figure things out, I like the approach of what I call being a “part-time quitter.”

The idea is that you’ll have enough income from your freelancing gigs to cover your monthly living expenses. Trying to fully replace your income may take longer than necessary is a drag if you’re miserable at your job. Plus, I don’t recommend completely booking yourself up and potentially being overwhelmed with work. For me, freelancing is about improving quality of life, not just money, so I didn’t want to jump into filling my days with work and feeling like I was back at a full-time job.

In my case, I wanted to have some time to enjoy the summer, so I was happy to work a little but not afraid to rely on savings a bit. My freelance work only took about 15 hours a week to complete when I first left my job, and this allowed me to travel and explore a lot more than if I’d had double or triple just the amount of work. Now I’m increasing my work load as I settle into my new lifestyle.


Be Mentally Ready

Making the switch is going to provide some challenges no matter how prepared you are. Your life might not be exactly as you imagined after leaving your job.

If you’ve taken a cut in your income, there are going to be times when dealing with money will be stressful. You may hit periods when freelance income slows down a bit, too. I’ve kept myself up at night a few times worrying over this, but having the 6 months of living expenses saved up eventually allows me to relax.

Also, having my fund allows me to make level-headed decisions and avoid undesirable freelance clients that I’m not excited to work with. I have faith in the process, and giving myself more time to get it all figured out is well worth the money I have saved.

Of course the whole experience of quitting your job and striking out on your own is incredibly invigorating. Even if things are a bit tumultuous, don’t forget to take it all in and enjoy the ride.

Have you thought about freelancing full-time and quitting your job? What’s stopping you from making the leap?

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About the author: Jeffrey Trull is a freelance writer, blogger and recent transplant to Portland, Oregon. You can check out his writer site, jeffreybtrull.com to find his work all over the web or head over to MoneySpruce.com where he helps 20-somethings sort out their money and career so they can spend on what they love.

Comments on this entry are closed.

  • Sean @ One Smart Dollar September 26, 2012, 9:21 am

    Jeffrey, congratulations on being fully on your own. It is a great feeling, but it can get stressful at times. My wife and I have been able to travel all over the world because of our lifestyle.

    • Jeffrey Trull September 26, 2012, 11:02 am

      Thanks, Sean! Travel is a big goal of mine right now, too, and I’m actually planning a month-long trip to Thailand and Europe as I write this. I could never do this if I still had my day job!

  • Jordann September 26, 2012, 10:35 am

    Freelancing full time would be scary to me, but I bet it would be highly rewarding as well. I think I’m too risk averse to take it on full time.

    • Jeffrey Trull September 26, 2012, 11:01 am

      Hi Jordann! You’re right, it is scary at times, and I think you do need to be willing to take on some risk. I still do recommend working as a part-time freelancer at first and getting a feel for it. No matter what your situation, I think it’s essential to have savings or a larger emergency fund in place for the times when income isn’t so steady.

      The upside for me is that I feel more in control and less at the whim of a company or boss when it comes to the work I do and the income I earn. And the lifestyle is highly rewarding and outweighs the risk in my life.

  • Lance@MoneyLife&More September 26, 2012, 11:14 am

    I have thought about it but would need to be making much much more to seriously consider it. I also have an awesome job right now and see no reason to make the jump unless it holds me back from potentially making even more money.

    • Jeffrey Trull September 26, 2012, 11:40 am

      Good points, Lance. The decision was certainly easier for me – I had a job that I didn’t love, and I also wanted to relocate from Connecticut. Freelancing full-time isn’t someone I would recommend to everyone, but I think it can be a very good alternative if you’re looking to change things up from the standard 9-5.

  • Modest Money September 26, 2012, 12:12 pm

    Good tips on making the transition. It’s definitely not something you want to jump into headfirst without proper planning. I know I’ve jumped into being my own boss only to realize that it would still take a while to get the income to the point I needed it to be at. That lack of patience put a lot of extra pressure on me and made it more difficult to build things up at my own pace. I don’t think I’d personally want to do freelancing full time, but being my own boss as a publisher and affiliate marketer is very appealing to me. It may be something I give another shot sometime soon.

    • Jeffrey Trull September 26, 2012, 12:45 pm

      I definitely agree that in most cases, you’re not going to as much money as you expect as quickly as you hope. But I think freelancing is more quickly accessible than other ways of making money online, and it’s also complementary to other areas like publishing.

      I’m not sure I’ll be a freelancer forever, and I aspire to do other entrepreneurial things, too. Freelancing has provided me with the lifestyle I’ve always wanted, and that’s worth more than additional money to me sometimes.

  • frugalportland September 26, 2012, 1:54 pm

    You’re so young, Jeffrey — do you think you’ll go back to the regular grind?

    • Jeffrey Trull September 26, 2012, 3:26 pm

      I don’t think that I will, and I hope I don’t have to. But if freelancing and working for myself wasn’t working out for whatever reason, I wouldn’t be entirely opposed to it.

  • Andrea September 26, 2012, 1:56 pm

    I think you were much better prepared than I was. It’s been nearly a year and I STILL haven’t attained much balance between work and personal. Then again, I switched gears a few months into my freelance career and have played catch up ever since.

    People just really need to be prepared; in fact, they should be overly prepared. You can never have too much in savings or spend too much time pondering before you quit your job. Some people are just not cut out to be self-employed, and I think it takes a lot of consideration to make the jump. My situation was kind of forced on me due to circumstances at my former job, but I’m glad I had already been planning for it or else it would have been a disaster!

    • Jeffrey Trull September 26, 2012, 3:28 pm

      I agree: it’s very hard and you can never be too prepared. However, I do believe that you should set a date and go for it eventually if that’s your goal. A lot of people spend time trying to plan out their lives and figure out every detail. In my case, I needed to make the leap and just be okay with some risk and uncertainty.

  • Greg@ClubThrifty September 26, 2012, 3:38 pm

    I would love for either my wife or I (or both) to be able to do this someday. We will need to wait until we have our house paid off however. Plus, we’ll need to be making much more in order to get there. We are trying the “part-time” quitter thing right now. We’ll see how that goes first:)
    Thanks for the great tips!

    • Jeffrey Trull September 27, 2012, 1:59 am

      You’re welcome, Greg! Good luck!

  • Mrs PoP @ PlantingOurPennies September 26, 2012, 5:46 pm

    I’d love to try it sometime, but not until we’ve got a lot less and even more investments that we can fall back on!

    • Jeffrey Trull September 27, 2012, 2:00 am

      Yup, I definitely recommend having at least something to fall back on because just about every freelancer needs that from time to time.

  • Robb @WatchOutForFlyingNinjas! September 26, 2012, 11:48 pm

    I think apart from trying to find something to do as a side job I don’t know if I’m ready for something like this, plus I’m having a lot of fun with my job so there isn’t a lot of want to break out of anything either.

    • Jeffrey Trull September 27, 2012, 2:00 am

      It’s just an option and not for everyone, Robb. If you love what you’re doing already, no need to change :)

  • Shannyn September 27, 2012, 6:19 pm

    Jeff & Carrie- whenever I get worried about my full time freelancing lifestyle I am reminded why our breed of people are awesome and why I need to keep hustlin… loved this article and it’s helping me as I reassess my priorities and build a life for myself in 2013. You rock!

  • Dana Leavy-Detrick October 1, 2012, 9:40 am

    One of the most important things Jeff mentioned in here is that, “For me, freelancing is about improving quality of life, not just money” and it’s easy to forget that motivator when you hit challenges. But that’s essentially why people make the shift. Many make it for bigger earning potential, or the ability to choose and work on more creative projects or clients, etc., but it’s ultimately a work and lifestyle change. I love and (sometimes) hate that at the same time – but it’s exciting and always bringing something new and interesting to the table. Thanks for sharing! Good points.

  • Brent Pittman October 1, 2012, 9:25 pm

    I would also like to become more location independent, but it gets harder with marriage and kids…not impossible, but the pressures of family are harder to escape.

  • AverageJoe October 4, 2012, 11:59 am

    Great advice. I especially like your advice to automate. I think it’d be tough to put 50% of your pay away if it wasn’t automatic.