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A Less Scary Way to Look at Self-Employment

When I first discovered MyWifeQuitHerJob.com, I was thrilled. For years, my wife and I have been discussing ways to gain financial independence so we could spend less time at our jobs, which we didn’t necessarily hate, but simply demanded too much of our time and energy. The best plan that we came up with was to buy a Powerball ticket every Wednesday and Saturday and cross our fingers. With somewhat disappointing returns, we’ve ramped up our efforts and have taken to crossing our toes, too. Still no luck.

Fast forward a couple of months, and now I’ve somewhat stumbled into gainful self-employment. Now, we’re working on transforming my wife into a professional shut-in, too.

I enjoy this resource that Steve has created because it gives a clear, concrete method for achieving what many of us who are planning on having children desperately want: to be able to stay at home with the kids without sacrificing income. Interestingly, as was pointed out earlier on the blog, one reader commented that he found the small business startup guide entirely too daunting, which compelled him to give up. This struck me for several reasons. Admittedly, I, too, found the guide a bit intimidating. But that’s because my journey to working at home was starkly different – and perhaps a bit easier.

Now, don’t get me wrong. I fully intend to apply a more methodical approach while attempting to liberate my spouse from the 9 to 5, simply because I think her situation merits it more. But I’d like to offer my story as a bit of contrast to the diligent checklist approach. It’s something I’ll call, an organic transition to self-employment.

I call it organic because I didn’t implement any conscious system or follow any certain steps to get to where I am today (I’m a full time freelance writer). It feels more like I willed myself into self-employment rather than getting there by brute force. For me, saying goodbye to the commute and the suffocating 9 to 5 work schedule has always been somewhat of a dream that I kept in the back of my mind. It was this – and the following five essentials – that I believe eventually made me my own boss.

Friends (and Spouses) with Benefits

When you’re undergoing a risky venture such as self-employment, you’re going to need some support – fiscally, emotionally and logistically. I’m lucky enough to get all of that from my spouse. Thanks to my full time job having pretty crumby benefits in the first place, I had already switched over to her medical insurance. Also, with her steady salary, we could keep paying the bills if I got off to a slow start.

For most of us, these two factors are probably the most comforting safeguards. But don’t downplay the value of emotional support. It’s good to have a co-pilot when you’re flying solo. And without a water cooler and the collective ire of your coworkers to help you process ideas, work out problems and vent your frustrations, you’ll definitely need an open ear and an open mind to keep you sane.

If you aren’t married or have some other kind of domestic support, it’s highly advisable to find a mentor or a group of friends with similar entrepreneurial aspirations.

A Little Bit of Experience

The hardest thing to do when striving to be self-employed is to figure out what exactly you’ll do to make money. The experts always give the exact same answer to this question: “Do what you love.” That advice is all well and good – but ultimately, it’s the same thing your high school counselor told you when giving you career advice. I followed that advice and did what I loved all throughout college (slept late, played video games, drank beer and ate pizza) and, unsurprisingly, landed myself a career that didn’t quite meet my expectations.

Instead, I would give this advice: don’t start from scratch. The easiest way to become gainfully self-employed is to take something that makes you a little bit of money and ramp it up so it makes you a lot of money. This may not be what you consider to be your “true calling” – meaning, you’re not going to take your job and shove it and then go become a painter or a dancer or a chef, because, unless you already have a bit of success in those fields, you’ll have to go back to school, get experience and get noticed again all from square one. Essentially, you’re not transitioning to a new career, you’re just starting over.

The danger of starting anew is that you’ll either find the task entirely too intimidating and give up before you start or you’ll simply end up having to make the same types of compromises that wound you up in the cubicle in the first place. By choosing something that already makes you money, all you have to do is figure out how to make the venture bigger and better.

In my case, I was lucky enough to land a gig in college writing web content. At the time, it was the perfect job. Before getting this gig, I was washing dishes in the cafeteria. After tipping over one too many towers of freshly washed glasses and making a paltry $7.50 an hour, I decided that there had to be some better way to spend my time in which my poor coordination wouldn’t pose a danger to my pride or any innocent bystanders. Through some thrice-removed personal connections, I ended up landing a position as a contractor for an SEO firm, where I wrote just a few articles per week, which wasn’t a lot of money, but it kept the pizzas and textbooks coming.

I did that all throughout college, which made it, in essence, my very first real job. And, not-so-coincidentally, it’s the same job I do today. After working for a couple years in the office and finding it unfulfilling, I decided that I wanted more control over my time and income. Copywriting on the web seemed like the obvious answer. I just needed to figure out a way to go from making a few hundred bucks a week to matching my current salary.

For you, your starter gig could be anything. Think of all the things that anyone has ever given you money for – these things are the valuable skills or products that you have to offer the world. You could learn how to market a craft through an online store (if so, you’ve really, really come to the right place), become a personal trainer, start a dog grooming and boarding business, sell things on eBay, build websites, design t-shirts, trick out cars, file income taxes, mow lawns. Chances are, you aren’t a one trick pony capable only of manning a cubicle. Find out what you already have to offer and slowly start building it into your main stream of income.

Read the rest of this story at MyWifeQuitHerJob.com.

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