Should you be self-employed?

Published on March 07, 2011 under Business, Career

Should you be self-employed?

It's the dream of many to be their own boss.  To set their own hours.  To make the rules and call the shots when it comes to making your livelihood.  Probably since day one of when I got into Interactive Media friends, family, and even total strangers have asked why I had not just started my own firm?

Granted I sort of did and still use the name "Orpheus Studios" as a "company name" and have tried to be a web design firm in the past.  However, my experiences don't generally match up with the fantasy of sleeping late, doing work in PJs, having 4-6 hour workdays, and making amazing money.

My Experience

After the dotcom crash in 2000, I was one of the many techies out of work with little to offer the economy that millions couldn't offer already.  I job-hunted, did some consulting for a company, and was getting closer to running out of unemployment.  I had landed myself a web site to design and build for a small business.  At this point I thought maybe I can make my living, at least for a while, on just these smaller web design jobs.

I was wrong.  One thing I've realized and I learned the hard way was how much that one job you think that will be done quickly won't get done quickly.  I dealt with clients who went bankrupt before I was to be paid.  Clients who wanted the site done in 2 months and stretched it out to a year with constant changes, rethinking, and taking a mile for the inch I'd give.  Plus the money in the end wasn't enough to pay rent and feed myself.  Not by a long shot.

I won't even get into the issues I had with family and friends who seemingly assumed I had loads of free time now.

Are you willing to do it all?

This is what in my book separates the workers from the entrepreneurs.  While my father and others were raised to be their own bosses, I found more comfort in the stability in being a valued employee in a bigger company.  I also think the main reason I like not being self-employed is that I don't have to do the things I hate in this work.  The handholding of the clients, sales calls and visits, the accounting, the proposal writing, the contract drawing, etc.  All that other work outside of the actual design and development of the project.

If you want to be your own boss, you have to be willing to do all this.  It doesn't matter if you just decide to do web work or accounting or carpentry on your own...or if you come up with an amazing idea and you could be the next Mark Zuckerburg.  You have to be willing and able to do more than just the one thing you feel you're good at and should be paid for.

Are you willing to suffer for possible success?

Let's make no mistake about it.  Even if you learn complex Java coding, Android, Objective-C, and iOS development, it doesn't mean you can set up shop and get paid loads of money easily for the skills you offer.  You might get a gig for six months and come away with six-figures, but then be out of work for a year because no one else is spending money on mobile projects.

I know one can look at the industry right now and think I'm crazy to think mobile would be in decline, but it can happen, and this is merely just a hypothetical example.  You could suddenly wake up and find millions of people ran out and learned programming now competing against you, or the big names that want apps only want to deal with big name digital agencies and not freelancers.  It can happen.  Look how many in construction are struggling right now because of the decline.  Look how many dentists are struggling to pay those student loans not only because patients are low on money and avoiding going in, but there is literally a dental office on every other block in most major cities.

You might not make big money regularly.  You might make some cash for now and then be struggling to get the next gig.  You might design that great online business, implement it, but not see any profits for years.  Look at and how long it took them.  If you're not willing to struggle for a while to possibly see success, then don't.

I know I'm making it sound terrible

Granted my words here would make many believe going self-employed or even entrepreneur is a doomed situation, but it is in the risk-takers that you see the success stories.  Many who started the biggest online ideas of now were willing to struggle to get there.  Some gave it all up and suffered while others treated their innovations as a moonlighting gig.  Wordpress, Twitter, Facebook,, these were all side ideas of their creators as they did their normal 9-5 job, and then one day they grew into their revenue stream.  Many app developers do this as well.  Even I do it with web work.  I'll still freelance, but I carry my normal stable job in an ad agency.

The Reality: Everyone is his or her own boss

Should you be self-employed?  The reality is you already are...even if you work for someone.  When you negotiate your salary and benefits, when you decide if you want to do a job or quit, even when you negotiate if you're going to work over the weekend or not.  That's you being your own boss.  When you figure out where your money goes and how you save for retirement, that's all being your own boss.  To think that working in a company means you are not self-employed is the wrong idea.

Believe it or not, you are in charge of your own career, and especially in this line of work, you're in charge of the direction you want it to go.  You might decide to be an entrepreneur and work on that great idea of yours, hoping to make millions from it, or know someone with a great idea and partner up to help them make it a reality.  You might decide that building inexpensive web sites for "mom and pop shops" and never seeing the inside of any office but your own is your desire, with all the other work that goes into it.  You might just want to remain freelance, bouncing from bigger player to the next and giving them the skills they need on a temporary well as getting some bigger clients under your belt.  Or you just might decide you like showing up someplace every day and not having to worry about anything other than your task and position.

The factor of if you should choose to be your own boss completely or partially comes down to what will serve your needs and career the best.  For me, I do better for myself by working in a big company where I can get into bigger jobs and yet keeping my free time open for my own pursuits.  I don't see a web design business as a larger benefit to my career or life, and I don't even see freelance as giving me the stability I want in my work.

Whatever choice you make, just make sure to bear in mind all the benefits and drawbacks that come with that choice.

Are you self-employed? Freelance? Entrepreneur? Or do you prefer working in a company?

Tags: career, self-employed, entrepreneur, business

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