Unfreelancing – Letting Go Of The Attractive Freelance Life

For years and years I worked on my own. Two months shy of six years, to be exact. I gave up all of the freedoms and self-employment perks in exchange for the shackles of servitude and obedience.

But I also left behind the stresses of the EDD, corporate taxes, business development, and operations management. Those management concerns all happened on top of designing and developing interactive applications and websites; usually at nights and on the weekends.

Making the switch definitely had it’s perks.

However, the transition was not easy at first. Soon though, the sense of confinement and control lifted and soon I came to enjoy the freedoms that accompany working for someone else:

  • My family is first priority, and now, when I’m not working, I’m not working. Being in management, I always need to be reachable and I do sometimes work long hours, but that is all up to my discretion. If my son has soccer practice, or my daughter wants me to read books to her all evening…that’s where you’ll find me. Overtime happens, but only if I want it to.
  • My job comes with a description, and while I tend to wear a bunch of hats, I know that I’m not responsible for everything. I don’t own the company, and that is just fine by me.
  • I don’t have to worry about making sure we’ve got enough projects or revenue to pay the employees.
  • They hand me checks twice a month. Look, I may have made more money as a freelancer, but I don’t ever need to experience another 3-month dry spell waiting on delinquent clients. I’ll gladly exchange a little dough for piece of mind. So will my wife, I’m sure.
  • I have 10x less paperwork every day. I really should repeat this one like Bart Simpson on a blackboard.
  • My office isn’t the spare room in my house, and my co-workers are actually a nerf football to the head away. I do not miss the solitude of freelancing, and I doubt I ever will. Collaboration is king.
  • When I need technology, software, fonts, resources, hardware, etc., my employers purchase these things…I don’t have to worry about mapping out purchases, and such. It’s not my job.
  • I can take sick or personal days off, delegate my work to my team, and know that things will be done. While I could take days off whenever I wanted to before…if I wasn’t working, things weren’t getting done.

Look, you can always make a very strong case for the freelancing life. It can be wildly lucrative, can allow you to work on a ton of great projects, travel, collab with a variety of different teams and agencies, and give you the ultimate scheduling flexibility.

But for me, it’s a lifestyle so much more befitting a single guy in his 20’s than a married father of 2 in his 30’s. I was so scared when I took my first job in July 2007, but in the past 18 months have really grown to love this balance I’ve found which was much more difficult to attain (and maintain) when I was running Go Farm or freelancing as 417north.

I’m a strong advocate for returning to the office. I have grown so much more as a designer, and as a creative director for heading up design teams for companies other than my own. I’m now directing an in-house design team (the in-house design life, that’s a whole other post), and that has brought even more lessons and growth.

If you enjoyed this article, please consider joining (or starting) the conversation by leaving a comment below. Thank you kindly.

There are 16 comments
  1. Lani

    I’m pretty sure this is the first time I’ve seen a positive spin on freelancing. During my last year in college, I was completely freaked out by the notion of freelancing by my own instructor. He would personally tell me about his struggles with freelancing, like almost getting evicted from his place because he didn’t have enough funds, not getting paid for six months, dealing with too demanding clients, not having a legally sound contract, and etc. I’m sure he brought some of the grief on himself, but those tales were enough to make me stay far away from freelancing. Eventually, my mind matured enough to realize that I should try to experience freelancing on my own, so I took on a project a few months ago. I must say it’s not that bad, but I was working two other jobs at the time, so I’m sure the project could have gone much more smoothly. Anyway, like you said, I would prefer the stability of working with a team or agency.

  2. New blog post: Unfreelancing – Letting Go Of The Attractive Freelance Life http://tinyurl.com/7ng8dt

  3. Champ

    Bro. You are bumming me out.

  4. Champ, don’t get bummed out man! I’m just giving my opinion. At some point in the future, I’m sure I’ll head back into the fray. It’s all about cycles.

    As for you Lani, I’m a little blown away to read that you’ve never heard someone speak about freelancing so positively. Especially considering this was meant to be advice against freelancing. In any case, here are some great resources for you:

    Hope this list helps you in your efforts freelancing. I know if I was out there on the hunt right now, I’d be checking these sites regularly.

    My best.

  5. Tansters

    First! High fives for your thoughtfulness and realness. We’re in the stages of doing our own thing / freelancing / freestyling! I love the pro’s and con’s listed. No doubt there is a balance to everything in life, the good with the bad – the success with the failure. Here I come spare bedroom!

  6. Chavi

    I recently left a design agency to work as a freelancer, and although it has it’s perks, i do miss some of the aspects of working for someone else, especially the paycheck twice a month, and not having to worry about all the administrative aspects of the company, but i have to say, the thing i miss the most is working with a bunch of cool people, it can get lonely/boring working alone at my place for hours on end, and coming from an agency and not some “regular job office” the working environment was pretty fun and laid back

  7. gREG

    I have to say Greg, I think you’ve got things backwards. Someone in his 20’s should feel free to be a corporate slave, and work long hours away from home. because there is no one at his home to worry about. When your working for someone else and they say work, you work. If your children need you, and your boss demands your time, then your boss wins.

    Your corporate job can establish a strong background for starting your own company in your 30’s. You can “freelance” if you wish, but I prefer being an entrepreneur. The only difference between your Boss and you, is he can be home with his kids if he wants to, and he makes more money. Granted, he also takes the risk… but guess what, if he doesn’t meet the bills in this horrible economy, you get fired, so what’s the difference?

    I am sure you have a great job, but imagine how much more of your children’s lives you will get to see if you were actually home during the day. Being your own boss doesn’t mean doing everything yourself. It means building a team, and delegating the work to that team.

    If your bad at working with people you can still delegate your work to other freelancers. Hire someone to do your psd to css work if thats your weak spot. Find another freelancer and start a partnership. Get a real business loan, so you can afford a couple of employees.

    Eitherway don’t give up time with your children.

  8. gREG, not sure if you read the article above, but I ran a successful freelance practice and then my own company for years and years. Actually, I don’t think I have it backwards at all. It was great to be able to pick up and roam the world whenever and wherever I wanted to. That’s not something I can do just as easily with a wife and two (three, shortly) kids.

    Someone in their 20’s has the opportunity to hang themselves out there a little bit when times are tough…slack that is not afforded you when you have other mouths to fill.

    I really don’t miss much more of my kids’ lives than I would otherwise. I get off of work a little earlier than most, because I get in a little earlier…and I also put in the necessary work in the evenings when I’ve got shit to get done.

    I made the decisions I did regarding working for someone else precisely because of my children, not in spite of them.

    It’s two different schools of thought – not one better than the other – but this is working swimmingly for me and my fam right now.

    Someday, the eventual goal (which I’m working towards as we speak) is to build up a nice collection of passive income streams. Then everything is negotiable.

    I want all my options open, as I’m not really sure that I want to have my own agency again anytime soon. After 10+ years of client work, I’m enjoying the break.

    Thanks for your input. It’s much appreciated. You’re widening the conversation…

  9. Kudos to you for making the switch. Over the last year I have found myself faced with a similar set of circumstances – early 30’s, 2 (soon to be 3) kids and (until 2008) a successful business. After a somewhat painful year of change & reflection I am pleased to say that I still opted for the freelance route, albeit in a much more structured and balanced manner than before. Tough times bring out positive change, and whatever your route I agree that life balance & taking care of your family is key. If you have found that balance through a 9-5 position, then that is pretty darn close to “living the dream”. Economies come and go, and those that can step back, change & adapt will persevere. To those out there fighting the same choices, consider a coach – the outside perspective can be an amazing help. Good luck & here’s to an awesome 2009.

  10. Backwards?? I think not, Greg. I for one, worked a lot of freelance jobs, and I also did the corporate thing. There is something to be said when you work freelance job aka for yourself and clients are not paying you on a timely manner, or you have to wait another three months to get the next gig. What do you then say to your kids, whom you are responsible for. What do you say when you have a sick child, and because you work for yourself, you don’t have the proper or affordable medical insurance to make your child well. Granted, there arguments to be made for both sides. But there’s far more stress working for yourself than working for someone else..in my humble opinion.

    Working corporate also means you have a standard 9 to 5 and you can come home at the end of the day and on the weekends to spend time with your kids. You are also granted paid time off, etc. When you work for yourself, you work more, more, more. I am Greg’s wife, and I work more hours because I work for myself. On vacations, I constantly have to have my blackberry handy at all times, because everyone answers to me, and when there’s trouble in paradise, guess who gets the call?

    Besides, your kids are home during the day? What happened to school? And if they are younger than 5, what happened to daycare? How do you get your job done when your kids are at home with you during the day? If I were a client, I don’t think I’d feel comfortable sourcing a job out to someone that is at home with their kids because I have been there…it affects not only your quality of work, but the time it takes to finish the work.

  11. Hi Greg & Folake,

    A nice article. It really open my mind now. Recently I’ve been seeking for some job opportunity in design companies. I found a lot of things that I can learn from various interviews. I found one company with it’s weird rules such as no talking to others when working or even no hang out after work with our own office colleague. So every time I get to this interviews, I always have the idea of “you know what I believe I can do better than this” or “GOD I can open a better design company” or if it’s gone really weird…”I miss my son”.

    So now it’s has been nearly 7 months looking for jobs and doing some small freelancing job. It’s quite depressing when you living with your saving and have a son to support. My wife is working at a international bank, so we got benefit for medical or health. I’m trying to stay positive but my boundaries always is it better to work alone or working in the office for someone else. I hate working alone though always enjoy the company of team or friends in the studio. When you’re alone on the job sometimes it kills you with dead end with solutions or just plain boring waiting for revisions.

    I love my son & wife but looking for 9-5 work it’s a bit luxury for creative environment in design studio. It really bothers me sometime when I take a look of the pictures of my son in mobile, it seems I lost his early years for working with someone else. My son is 2 years old now.

    I dream to own a studio but is it feasible this year? It seems everything is getting worst than ever.


  12. gREG

    I am obviously on the fringe of the freelance vs. corporate debate. Your points about stress are right on.And it keeps coming back to passive income streams that you mentioned. (This blog keep up the hardwork because we love reading it) If I had to worry about my web design being a primary source of income (especially the sole source of income) I would never work for myself.

    It’s also clear from both of your posts that your most likely in a much higher income bracket than I am, and are probably a bit older than me. Which has a huge bearing on where you fall in the freelance vs. corporate debate.

    Your post struck a strong cord with me because I’ve been moving my whole working career away from corporate and towards ownership of my work. Please don’t take offense in my comments, I have started the conversion too seriously!

  13. Andiran – If I may chime in (and ignore me please if this is unwarranted) I really truly feel your pain. What worked for me was finding a business coach. It was a strange (and expensive) proposition at a very awkward juncture, but the detached, non-emotional advice saved me. Creative work is tough to evaluate clinically – at least for me there is an emotion wrapped up in there & then when you add the family duties to the mix it becomes a very large ball of conflicting & unresolved stress. My first 6 weeks of meeting with a coach were focused on helping me re-enter the traditional job market. I also went to a number of very strange, very unappealing interviews. It was a humbling process. Working through this with someone who is completely uninvolved in anything other than your success was a big help – we did come around to the conclusion that for me, remaining self-employed was the best bet. HOWEVER, everything I had been doing had to change, and the entire focus of my business had to change as well. It seemed unpleasant at first, but the results have been astounding. In a sense, I am back doing work I used to do years ago in my career. In another sense, I am doing many things differently than my competition because I now have varied, wide-ranging experience. This in turn sets my work apart, and has resulted in an increase in business even as times get tougher.

    Perhaps the best piece of advice I received was that when people smell your fear (and trust me they can) you will never get anything other than “pity” work – meaning short term jobs, meager wage etc.. You have to “own it baby” – stick to what you are good at, kick ass at it & people will come – in times of turmoil EVERYONE is looking for someone to help them, you just have to be that guy.

  14. to Dave deBruyn,
    Thank you for your kind and great respond. Your words truly inspire me to look up and forward without hesitation. The “smell your fear” is quite strong point for me. I did open your site, so you opened doors to other fields also? interior, etc. I also learn that you focused on a segmented market too.
    So I guess one of my plan is to find a business coach to help me define my market for opening a studio.

    One of my greatest fear when working with somebody is when the company I work for went bust or something, than I have to find another job only to find out that not so many studio out there want to hire anyone above 30. So the freelance and establishing studio will be a moving back up plan for me. That’s one of my idea.

    Thank you.


  15. Hi Andrian. Part of my “restructure” was to focus on a niche and then be the best at that niche (again good advice from the coach – Thanks Alanna!). I chose to focus on the Real Estate part of my Design business as it was something I am quite passionate about. What is truly interesting is that even though I am now focused on a very small niche, I am getting an increasing number of requests for work from completely unrelated industries. I guess at the end of the day it was a lot easier to be the best in a niche, than try to be the best all-around design+marketing firm. It has also allowed me the time to focus my energy in a single and clear direction.

    As far as opening a studio, I find that it is now very viable to operate in a virtual manner via strategic alliances. Find like minded people who do good quality work, and commission them as required. Without the stress of a brick & mortar operation, employees, benefits etc you will be much freer to adapt to the changes within the industry. For example, my copywriter and Jr. artist both have day jobs, but I pay them well for the work that they do, when required. This allows for growth, without being tied down. Good luck in your (ad)venture!

  16. I wanted to comment and thank the author, good stuff

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