A Less Scary Way to Look at Self-Employment

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Every entrepreneur takes their own unique path and it’s always interesting to hear things from a different perspective . In this guest post by Jack Busch, Jack tells his story of how he became self-employed.

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.


This, I would say, was the single most important aspect that contributed to my eventual full time self-employment. The biggest roadblock to building a side business to replace your day job is that you are only one person.

In the beginning, when your side venture is just a fledgling and requires very little time and attention, it’s pretty simple to wake up an hour or two early each morning, answer some business related emails during lunch and maybe log on once more before going to bed. (After all, it’s extremely bad form to work another job while punched in at your 9 to 5.)

But as your business starts gaining traction, it becomes increasingly more important that you spend a considerable amount of time speaking with prospective clients on the phone or face-to-face during business hours or rush a test project through with flying colors.

All the while, you want to continue giving your existing clients the same level of service you did when they were your one and only.

So, you have a couple options: Start slacking on your 9 to 5; burn the candle at both ends until you’re burnt out, friendless and permanently consigned to the doghouse by your spouse; let your thriving side venture languish; or get some expendable help.

For me, I had two extremely valuable agents of scalability: an income stream that allowed me to do as little or as much work as I wanted without getting fired and, more importantly, subcontractors.

Demand Studios

Regarding the variable income stream, I’m not too embarrassed to admit that this was Demand Studios. Much maligned by certain segments of the freelancing community, Demand Studios is the quintessential content mill, churning out hundreds of thousands of passable quality articles a day and paying out a flat rate to writers.

Say what you will, but the system is brilliant, both from a publisher’s and a freelancer’s standpoint. Writers can basically shop for topics and toss them into their queue and have one week to pound them out.

For a freelancer, the topics are hit and miss – you could get paid $15 to write “About Boiled Eggs” in 15 minutes (a dollar a minute!) but you could also spend two hours sifting through the U.S. Trademarks and Patent Office database trying to figure out who the hell invented the first Ziploc bag (pro tip: most of the info on this topic that’s already available on the web is bunk).

Demand Studios isn’t exactly resume material – but its value as a backup plan is obvious. Once I landed an account at Demand, I had a reliable (though sometimes mind numbing) source of income I could fall back on if times were tough, but, more importantly, I could completely ignore it when I didn’t need it. It’s like the freelancer equivalent of a booty call.


The issue of subcontractors is a bit controversial – especially in my line of business. On the one hand, if I “buy” the rights to some text from another writer, I am legally free to put my name on it and sell it to another client as my own.

(Kind of like when Edison bought the rights to tell everyone he invented the Vitascope.) But on the other hand, when I sell myself to a client on my own skills and my own samples, they have a right to expect that they’ll get copy that has been produced by me.

If you decide to go the subcontractor route, it’s good form to be upfront about outsourcing your work, or, at the very least, make sure that the subcontractor is on par with your style and quality.

Anyway, while I was working a fulltime job and seeking out new clients, I hired about five subcontractors to handle my overflow and take on some of the more repetitive work.

I didn’t profit from this, but it did solve one important problem: with a full time job, I didn’t have time to handle the fruits of my marketing efforts.

Subcontractors helped immensely with this. After all, the biggest demand on your time as you are building a client base is making initial contact, banging out the details of the contract, delivering a sample and working out any tweaks or adjustments to meet the client’s needs.

Once all that is done, it’s just rinse and repeat – something that a hired gun can easily achieve by referencing your example.

When I did finally take the leap and say goodbye to my salaried job, I simply scaled down from five subcontractors to just one or two. And because the subcontractors were mostly college students and retirees looking to make a few bucks here and there, rather than support a family on the money, there really wasn’t any love lost when I cut them loose (or, more accurately, stopped sending them assignments).

Your methods may be different. But in order to make a smooth and easy transition from working full time for The Man to working towards self sufficiency, it’s best to have a way to keep business on the backburner until you’re ready to get cooking.

The Marketing Machine

Before I started my business, I read this horrendously outdated book entitled “How to Start a Copywriting Business.” While the material regarding the Internet was less than insightful (Thankfully, the book has since been updated, but in my edition, the author was balking at the hundreds of dollars it cost to get a domain name), the author mentioned the prudence of building a “lead generation” machine.

He basically described it as a process that yields a predictable amount of leads each time – even if that percentage is very low. For example, if you sent out 500 direct mailings with only a 1% success rate of getting a bite, then you would still be getting five leads each time you did this.

So, in theory, if you “pulled the lever” once a week, you’d easily have 260 leads by the end of the year – not bad.

For me, my marketing machine was the Internet – job boards, Craigslist, old contacts, etc. I made it a habit to apply for every single gig I saw during my lunch break. It was tedious to write so many cover letters, but it paid off in the end.

About 71% of the leads proved to be scams or unresponsive, but the remaining portion that ended up being lucrative relationships more than compensated the effort.

I even forced myself to look for jobs even when I didn’t need the work – even now, months and months later, I’ll get an email response to a query saying, “Hey, can you still do some work?”

Just like long hauls on the highway, it’s better to top off the tank when you’ve got the chance than to find yourself frantically searching for a gas station when you’re running on fumes.

Good Timing

I was ready to walk away from my job over a year before I actually did. In fact, I was just about to do so, and then all hell break loose on the U.S. economy.

The company I worked for was directly tied to the finance industry and it got hit hard – the floor dropped out like the Tower of Terror and business plummeted immediately. Layoffs were inevitable and I was lucky to survive. As empty desks began dotting our office, I began considering resigning in order to spare some of my coworkers – but for some reason, I didn’t, which proved to be a lucky whim.

Thankfully, the paucity of business was short-lived, and the orders started filtering in at the same rate as before the fallout, but now with a fraction of the staff.

After the dust settled, I re-evaluated my situation and decided I still wanted to walk way. But by then, the stakes were different. Rather than eagerly letting me go as part of sweeping downsizing, I was walking away when the company needed experienced workers the most. Because of this, we worked out a deal: I would cease being an employee but would occasionally be available to do work on a contract basis.

It was a win-win situation: I had freed myself from the obligation to be in the office from 9 to 5 (and oftentimes, beyond) and they weren’t forced to scramble to hire and train someone new to replace me just yet.

Plus, I had essentially just landed my biggest client to date. And there I was: I took my subcontracted work off the backburner, I kept working for my old company and I continued hunting down new clients. I was self-employed.

Your day job may be different, but chances are, if you are a valued employee, you will be able to work something out. Because I had all the other irons in the fire, I had the confidence to approach my supervisor with an alternative to outright resignation.

There were a couple different options on the table, which would’ve helped me grow my business while easing back on my responsibilities to my old employer, such as working part time, working four day work weeks or working remotely full time that may work better for you.

I would encourage you to stay on good terms with your employer, even though you plan on jumping ship, as it will make negotiations much more cordial and productive, and most importantly, most beneficial for all parties.

I hope my personal take on becoming self-employed was helpful. I won’t say that I didn’t have to work a bit to get here, but looking back, I can’t really identify a time where I was diligently applying any sort of plan or breaking my neck to make it all happen.

True, my road to self-employment is heavily paved with luck, but still, I think what carried me here was the will to make it work, more than a conscious plan. I love what Steve’s blog has to offer and I think it should be required reading for anyone looking to strike out alone.

But hopefully, my story will show you that self-employment isn’t as hard as it seems.

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11 thoughts on “A Less Scary Way to Look at Self-Employment”

  1. Great post! Being an entrepreneurs involves great risk but also great rewards and fulfillment. It is more than a career move, in fact sometimes it is a calling and it really beats the hell out of working for someone else!

  2. Helen says:

    Really like this article,the first sentence you wrote about every entrepreneur takes their own unique path , watched a recent documentary about today young entrepreneurs, they did take an unconventional path to start their business, interesting movie – ”The YES Movie ” by Louis Lautman

  3. As you might know, the “online writing world” is up in arms over the alleged evils of content mills like Demand Studios.

    If more people took your perspective, I think it would be a bit more productive. There’s room to use these opportunities when they meet your individual needs. Nothing more. Nothing less.

  4. Great Post. You’ve got some very good ideas in there. I think the most important part of Self Employment is the comfort level that you have with that life style. Some people are driven to be self employed and others avoid it like the plague. The key is to try and get work that makes you happy. That may be as part of a company or it may mean you need to spread your wings and go solo. Just make sure you’re into either decision so that you don’t 2nd guess yourself all the time.

    Once again, Great Post!!!

  5. I just submitted my resignation recently to pursue this path. I have a nice job but it really robs out my time to do the things I love and Im no longer happy in those routines. I felt that it limits my growth as a person and I have no regrets.

    Like in your story you went to things that you are doing during your college days. Its so nice to know that you have same thing because I can relate with that. What I do before I got the job still the things Im doing right now.. and I believe this is really where I belong to..

    This is a great guide. Thanks.

  6. Nico says:

    Hi, I started a business quite a few times before in the past. The one time I involved my dad to be part of the business(He does not know how to use business money sparingly – unfortunately), then also I went into business with a friend who didn’t treat me right financially(did deals behind my back without giving me my due), then I also did another business totally on my own, but it involved walking from door to door and speaking to numerous customers, getting shouted at by some, done in by others, and also congratulated by the rest. This was my most satisfactory business I ever did(except for the shouting and the lot of walking).
    But now today this business doesn’t seem to be profittable enough like it used to be in the past(copy cats).
    But I have an idea on improving the product which could then even go international.

    I like what I see about others also in the same boat, having the same frustrations etc doing their own thing after realising that they are well able to.
    This is very incourageing !

  7. This spoke of how to be strategic in becoming self employed. Which definitely made sense because of tremendous reality of a mind shift that occurs in this process. Gladly this post talked about a skillset needing to already be in place before the transition. In my opinion having those skills from previous work experiences being used in your business will give it a better chance of success.

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