Tech & Work

The most terrifying way to earn more money

Striking out on your own can be a terrible proposition. But Greg Miliates, who's been there himself, offers some tips for overcoming those fears and making it work.

Before I get started, I just want to mention that there are actually lots of terrifying ways to earn more money, like:
  • being an arms dealer,
  • creating a meth empire in your town,
  • being a drug mule for a Mexican cartel, or
  • being a clown at children's birthday parties

But for the moment, I'm going to focus on confronting your fears and turning your tech skills into a business. If you're so inclined, you can tackle those other terrifying ways to make more money; facing your inner fears is a big enough challenge for most of us (though you won't catch me in floppy shoes and a rainbow wig singing to kindergarteners anytime soon).

We all want to earn more money, but as an employee, it can be scary to think about using your tech skills to create a business—even though you know your skills are marketable. Starting a business is daunting, and riddled with anxiety and the fear of failing. I've seen lots of people—myself included—who didn't know where to start, thought that starting a business was something that only "other people" could do, were afraid to fail, or were afraid they'd lose money and time on a failed business. (We've all heard horror stories about people who lost their life savings on a failed business.) The result is that even if you want to turn your tech skills into a business, those fears can paralyze you.

But the fact is, those fears are either false or blown way out of proportion. Even so, it's hard to shake them off. But there are specific strategies and tactics you can use to beat those fears, and start down the road to using your tech skills in your own business. The benefit is that by beating your fears, you'll change your worldview, and see that you're capable of much more than you thought.

Why fear paralyzes us

The most common fears are about turning your tech skills into a business are related to:

  • failing
  • not being perfect
  • not knowing where to start
  • being rejected
  • losing money or time
  • looking foolish

But those fears are either blown out of proportion or not based in reality. For example,

  • Would you really be a failure as a human being if you tried starting a business and it didn't succeed?
  • Does something really need to be perfect for it to work? How many businesses and products aren't perfect but are still successful? Every successful business is imperfect. Think of all the software bugs and marketing gaffes from Microsoft, Apple, or any company.
  • Is there only one right way to start something? Or are there many paths to success?
  • If someone doesn't need what you're selling, does that really mean you're a worthless human being?
  • Are you really guaranteed to lose money and time by trying to start a business? Do you really need to burn through your life savings and years of your life to start a business?
  • Will you really be a fool for trying to start a business? Will you actually be publicly ridiculed for your efforts?

So, even though you can see how your fears are unrealistic, they still have a strong hold on you and are hard to rationalize away. That gut feeling is what keeps us from acting in the face of fear. The brain may say, "Let's give it a shot" but the gut is screaming, "Get me out of here!" You can't reason with a rabid dog.

How taking small actions dispels your fears

We're not going to do therapy here, but the ideas behind the tactics below are based in cognitive-behavioral therapy, which has decades of demonstrated success in eliminating fears, anxieties, and phobias. For the moment, just know that you can work both sides of the street (change your behavior or change your thinking) to get past your fears. We'll do a little of both.

How to take action

The first step is to take action—small actions—that move you forward and give you a taste of success. Those tiny actions are the keys to beating your fears, since those actions will start changing your mindset.

Here are a few things you can do to start breaking down those unfounded fears: Do something every single day to move you toward your goal, and write it down in a journal. That way, you'll see your progress over time, and can see that even seemingly small actions will snowball to create big wins. The more actions you take, the more you convince yourself that you can succeed. Cultivate an experimentation mindset.This is one of the most important things you can do to demolish your fears. Remember:There is no failure—only learning. When you have an attitude of trying things out quickly and cheaply, the risk is very low, but the rewards are huge. You'll learn a ton about what works and what doesn't, but more important, you'll see that you don't have to take huge, life-crippling risks to start a business. If you've heard of the Lean Startup model, this is essentially what you'll be doing. Try things out—quickly and cheaply—and iterate based on what you learn. For example, if you think there might be a market for your PHP skills, DON'T waste hours and get discouraged making a bunch of cold calls to prospective clients only to get shot down; instead, surf around on sites like ODesk or Guru to see if people are paying for those skills. That'd take less than five minutes, and will validate that, yes, there are plenty of people willing to pay for PHP skills. (Yes, there's a big market that treats tech skills as a commodity and drives the price down, but putting yourself in a small, profitable niche lets you charge a huge premium—and have less competition). The point is to try things out, learn, and move forward based on what you've learned. Train yourself to look for problems.What are the biggest pain points you can solve? Don't limit this to just looking for problems where you work. Look for problems all around you. Does that restaurant down the street have great food but lousy service? That problem is an opportunity. Can't figure out something interesting to do in your town? That's an opportunity. You don't have to pursue all the opportunities you see; the point is to begin looking at the world through an entrepreneurial lens. People will pay generously to have their problems go away, and seeing problems as opportunities is one step toward getting rid of your fears and realizing how many opportunities there are. Become a strategic complainer. Maybe you hate your day job and want to ditch it. Use that negative energy to fuel your start-up motivation. Be careful about this though, because no one likes being around a complainer. The point here is to make your current job so unattractive that you'll be more afraid to stay there compared to starting a freelance/consulting business. Reframe the risks. Reframing your situation can do wonders for switching your mindset. For example, what would you lose out on by staying at your current job for the next five, ten, or 20 years? By comparison, trying a few small experiments and earning some cash from some part-time consulting gigs seems really low-risk. Look for specific ways you can increase revenue or decrease costs.This is a bit more specific than just looking for problems and re-framing them as opportunities. Remember: entrepreneurs create value, and typically, that value is either an increase in revenue or a decrease in costs. You don't even need to act on your ideas—yet. The point is to jot them down; that way, you'll realize how many opportunities there are even in your little slice of the world. Don't limit yourself to thinking about how to increase revenue/decrease costs at your job/company. ALL businesses—and people—can benefit from having more cash and/or lower expenses. Many businesses have big expenses that could be easily reduced using current technology. As tech workers, we're more likely to be in the know about cost-saving tools and services, and that knowledge makes it easy for us to provide value by cutting costs. The examples below could easily be implemented at most small and mid-sized businesses, but could also apply to larger businesses. For example:
  • Could the business switch from physical to virtual servers?
  • For phone service, instead of sticking with traditional phone companies and landlines, could they switch to VOIP and a service like Skype, Google Voice, or RingCentral?
  • Can they ditch their fax machines (and dedicated landline for their fax), and use an online faxing service?
  • Could they reduce postage by faxing and sharing documents in the cloud?
  • Could they eliminate courier costs by using a document e-signing service like EchoSign?
  • Could on-site tech support be provided remotely using tools like GoToMeeting or LogMeIn?
  • Maybe the company doesn't need a huge, complicated project management system, and could instead use a system like Basecamp to simplify project management for a much lower cost.
Start small, and part-time (do NOT quit your job—yet). Even if you have a huge consulting client waiting to pay you a pile of cash, try to start your business part-time. That huge client may flake out, and you want to make sure you can still pay your bills. Use your day job to fund your business. Focus on getting your first client, and making that client so happy that they'll be delighted to refer you to others. Then get your second client, and keep growing. When I started my consulting business, I worked full-time (along with being married and having two kids), and did the consulting on the side. At the point where my day job got in the way of how much I could earn consulting—and since my consulting income was relatively steady—I downsized my day job to part-time, ramped up my consulting workload and client base, then quit my day job completely. I'm pretty risk-averse, but ditching my day job for full-time self-employment didn't seem risky—it was a no-brainer, since I'd established a track record over the prior months for how much I could consistently earn consulting.

It's not so terrifying anymore. So what's next?

For many IT professionals, starting a consulting or freelance business is typically much easier than they originally thought, ends up creating a tidy side income, and can even grow into a full-time job. You already have the marketable tech skills, but getting past those initial fears is the price of admission to creating a profitable business—and ultimately changing your life.

And who knows? One day, you may find yourself with a red plastic nose, doing your plate-spinning act, and singing Happy Birthday. And no matter what anyone else says, it's a better gig than walking across the border with your underwear full of cocaine.

Greg Miliates started his consulting business in 2007, quadrupled his salary, and ditched his day job along the way. His blog ( gives specific strategies, tactics, and tools for creating a successful consulting business on the cheap.



Greg Miliates started his consulting business in 2007 and quadrupled his former day-job salary. His blog ( gives specific tips, tricks, techniques, and tools for starting and running a successful consulting business ...

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