What’s the Career Path for Ambitious Freelancers?

“I’m just freelancing while I’m looking for a job.” “I’m just freelancing while I build up my company.” “I’m just freelancing until something better comes along.” It’s easy to come to the conclusion that any ambitious freelancer is looking to get out of the freelancing game. But the fact of the matter is that there are plenty of freelancers in it for the long haul. Freelancing isn’t just a way to pay the bills — it’s a career path.
But the question of just where ambitious freelancers are headed is a tough one. Unlike a career working for the man, there isn’t exactly a clear corporate ladder to climb. We don’t have the opportunity to change job titles too often, beyond the ‘freelance rockstar’ descriptors we give ourselves. So, what’s an ambitious freelancer to do?
Look at the Money
We aren’t a bunch of mercenaries, but the bottom line is important to freelancers. Better paying clients is an ambition that we can work towards — while the dollar amount may not be the most important thing if your reasons for freelancing focused more on a question like flexibility, higher pay rates make it easier to take advantage of flexibility and even cut down on work. It’s easy to make jokes about living on ramen in lean months, but when a freelancer can raise her rates, she can essentially buy security. Higher rates can mean a fatter savings account, more days off and other benefits.
There is something of an upper limit when it comes to rates, though — especially if you charge per hour. You can keep raising your rates, but that doesn’t mean that any client is going to be willing to pay $5,000 for one hour of work. That doesn’t mean that you can’t keep moving forward with your freelance career, but it may mean that the way you move forward requires some consideration.
Working with the Right Clients
Who doesn’t have a client that you wouldn’t do just about anything to work with? For me, it’s one particular magazine that I’d be willing to write free content for, as long as I get my name on that page. Working your way up to the point that you can pitch your dream client — or, even better, have them come to you — is well worth working towards.
There are a lot more dream clients out there than there are rate hikes, too.
Think Big
No two freelance careers are going to look identical. That means that your ambitions may not match up with the next graphic designer over. If your ambitions are to use freelancing as a spring board to something very different, that’s cool. If your ambitions are within freelancing, that’s also cool. The important thing is to have ambitions that will get you where you want to go.
The alternative is to simply stick at your current level of freelancing forever, maybe edging up just a bit. That is, of course, anyone’s prerogative — but it doesn’t appeal to me and most of the freelancers I know personally. We got into freelancing to get rid of limits, from bosses to commutes. Not having goals or ambitions is just a round about way to impose our own limits.
So, what are your ambitions? Where is your freelance career headed?



Thanks for the reminder to dream, plan and act…
I started out as an ‘Accidental Freelancer’ over 12+ years ago. I never planned to freelance – circumstance created the opportunity and I thought WOW is that really what I’m worth to a company! I realized that as a regular employee I was being ripped off.
Over the past 2+ years I’ve changed my perspective to take on work that is net based, and develop several different income streams within the industry. I see it as planting seeds for my future.
The industry itself is changing so rapidly that as some opportunities fade, new opportunities, requiring a new skillsets are being created. I’m often looking for new opportunities and I sometimes have to restrain myself as I have a tendency to have to many irons in the fire.
One thing I can add is don’t be afraid of failure – it it’s only a failure if you don’t learn anything from the experience.
I’d say it would be to take on staff, and run a business.
or at least to take on a manager, and other designers/developers/creative bods, and then let someone else run and you just take a slice of the profit home!!!
Some really interesting ideas for freelancers. I’ve been working freelance and found starting my own company and ideas was the best way to go. I think freelancing is just a natural progression for entrepreneurs regardless of where we end up 5-10 years down the road.
Thursday, my main achievement with my freelance writing career over the last couple of years has been winning higher paying projects This has allowed me to make a lot of progress on an important goal: working less so I have more time for all the fun things in life.
Great points. For me I get in the mindset of that I am just freelancing while building my business, but really my freelance is my business.
I think pretty similarly to Dan Howard above…. I like freelancing, but since the very beginning I have been trading as a company. 10 years down the line, I’m starting to get the seeds of what might grow from just me into something bigger. I’ve had dreams of having an office / staff like Chase Jarvis since I was in school. Good to have a dream, a need to grow and build. I don’t do it for the money alone – I dream of building a legacy of some kind.
I am just thinking what I should go.. leave my work and be a freelancer or work at permanantly. So hard to make a decision.
I am just thinking what I should go.. leave my work and be a freelancer or work at permanently. So hard to make a decision.
This HAS to be the right career for me.
I just graduated and, after years of focusing on jobs that will make me comfortable/wealthy, freelancing started a fire in me. Other career paths did nothing for me. I only considered them because I couldn’t decide what I wanted to do.
I just wish I’d started on this path sooner. Tamixes, you’re right that we shouldn’t fear failure. One rejection last year put me off freelancing because I was sick of rejections from submitting novels.
This time will be different. I will start small and work my way up to a comfortable lifestyle doing what I love – writing.
My ambition now is to make enough money to enjoy my freedom. I love traveling and I won’t go to the “next level” (getting an office and employers), since it would get me back to “slavery” and the “9 to 5″ I’ve always hated.
Right now I earn enough on my own and would love keeping it that way.
The typical mistake of freelancers or small businesses in general is underpricing your work for lack of experience. Doing this right involves, as you mention, thinking about the money aspect of your works, and also dealing with the right clients. It’s not granted at all that a client will realize the amount of work behind a project, hence justifying the price. I think that’s one of the early hard lessons a freelancer has to go through.
My goal as a freelancer is to take it to a level where i’ll get payed 5 times as much as at the moment, and in the meantime develop a product that would sell itself and make money with virtualy no work at all.
And of course to work from the beach under the shade of a palmtree
I agree with Dan and Aaron, and kind of followed that same route. I started freelancing in college and still continue to do some projects under that brand and on my own. However along the way I formed a company with my father and another freelancer to start our own agency. It always had kind of a freelance vibe to it as most of our employees are freelancers. It’s kind of a good hybrid approach. It has also allowed us to work on our own projects and start up our own internal or spin-off companies.
I started freelancing out of curiosity… and never thought I’d be doing it full time for two years running. I’d say you’re right that it’s a career path, not just another gig to earn money for the mean time. If it wasn’t for freelancing, I wouldn’t have found my true passion and knack for creating copies that sell like pancakes ( and I can still recall my teachers back then calling me a giant nut case ). I’m glad I’ve found my place at last that the money I make is like a bonus in doing what I truly love.
When I first read this post my immediate reply is that my career path leads to retired. Then I thought about it and realized that I will probably be doing this until my final day. There is just something so sweet about doing what you love. The world would be a happier place if we encouraged this as a culture.
My reason for freelancing was simply never having to work for someone else again – if I can feed myself freelancing them my ambitions are fulfilled! I don’t want to take on a staff and be a boss, that would be too much like having a proper job again