How I Made 'The Leap' (and why you can, too)

Posted by JD McNamara on July 18, 2013

A few weeks ago, I officially made The Leap - that is, I quit my steady day job to launch my own business. The realization that I no longer had to battle traffic to get to an office I didn’t want to be at and do work that often frustrated me was extremely liberating...for a day or two. But then I blinked and had a to-do list a mile long (much of it housekeeping stuff that’s no fun to deal with) and not a single client (which means no money coming in). Wait, no money coming in!? And I did this voluntarily?

Yes. And more people are getting just as crazy (or smart) as me, apparently.

Everybody's Doing It

Okay not everybody, but according to the 2012 Global Entrepreneurship Monitor (GEM) Global Report by Babson College and Baruch College, the average Total Early-Stage Entrepreneurial Activity rate (TEA) increased to nearly 13 percent in the US (an all-time high since tracking started in 1999), 9 percent in the United Kingdom and 11 percent in Australia (as of 2011).


Entrepreneurship for Opportunity, Not Necessity

The GEM Report's lead author, Donna J. Kelley, an Associate Professor of Entrepreneurship at Babson College commented that of the aforementioned 13 percent of the U.S. adult population engaged in entrepreneurship "...the vast majority [are] starting businesses to pursue an opportunity rather than out of necessity."


The data shows that over 70 percent of Australians engaged in TEA are either driven by opportunity (as opposed to not having any other option for work) or the desire to be independent and generate a higher income (instead of simply maintaining an income). In the United States, the number is 60 percent, while the percentage of those engaged in improvement-driven TEA in the United Kingdom is just above 40.

The conclusions from these stats are that a) more people are becoming entrepreneurs and b) the vast majority are choosing to make The Leap (just like I did).

How and Why I Became An Entrepreneur (and how and why you can become one too)

Before I delve into the reasons I quit my job and started my own business, I want to acknowledge that it hasn't been any easy process thus far and I understand that it's not going to get any easier. There are pros and cons to taking The Leap, both of which I'll discuss. 

One of the hardest decisions I had to face when I quit my job was leaving my incredible girlfriend, Lyana (who you might be hearing from on the blog very soon), in a bind since we worked very closely (and very well) prior to my exodus. But it was the right decision for both of us and I'm a lucky enough guy that she totally supported me even though it meant things would be harder for her in the short term.

Despite that, my attitude, especially right now, is skewed quite positively towards entrepreneurship, but don't assume that means I think it's a walk in the park (or the solution to all work-related issues). 

Making The Leap is, however, an option for many people (some of whom may not even realize it). So it's to those people who are contemplating their own business, wondering how to get started, and asking whether it's worth the risk to whom I'd like to provide an account of my own experiences in hopes that it might make their decision a little easier.

Here's how I worked up the courage to quit my job and a few of the things that helped me make The Leap:

The Dream of Loving Your 'Job'

Love him or hate him, Steve Jobs said some truly wonderful and inspiring things. I often think of the following quote when I'm faced with any sort of work-related problem or stress:

"Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it." - Steve Jobs

How It Helped Me - I've always had a very romanticized view of what it meant to work for a living and, to this day, assumed that I would end up doing something I love. When I was younger, I'd say I wanted to be an archeologist or an astronaut, but that's probably because I'd just finished watching Indiana Jones or Armageddon. What I saw was a profession that looked fun, and I wanted to have fun with my work.

Fast-forward 10 years and I found myself at a job that I definitely did not love. After about eight months, I thought of Steve Jobs' quote almost daily. I'm actually not sure how I lasted as long as I did (almost a full 10 months more); I think most of it is because I worked with a certain wonderful someone and we were able to keep each other going.

But eventually, the wise words of Steve Jobs airlifted me out of an unsatisfying position and helped set me on a course to doing great work that I love.

How It Could Help You - Read the Steve Jobs quote and think about it every day at lunch. While you're eating, ask yourself the following questions:

Do you love your job?
Are you satisfied by your job?
Do you believe that you do great work?
Have you 'settled' for your current job because it seems easier than any alternative?

If you answer 'yes' to two or more of these questions for a few days in a row, you may have settled for the wrong job. The first step towards finding a better job or making The Leap is allowing yourself to believe that you deserve to do satisfying work that you love, and then getting past the notion that jobs are hard to come by and that you're lucky to even have one. That's no way to work and it's certainly no way to live.

Always remember what Mr. Jobs said: "If you haven’t found it yet, keep looking. Don’t settle."

The Start-up of You

I think some people naturally have an entrepreneurial spirit, and although I'm a newly minted entrepreneur, I think I've always had that spirit. Earlier this year, Reid Hoffman, Co-founder of LinkedIn, and Author/Entrepreneur Ben Casnocha released a slidedeck called 'Start-up of You' that outlines the tools and mindset of entrepreneurs (and how the spirit can be applied to careers as well). Here's the deck:


How It Helped Me: While this deck is a great resource and something I've definitely consulted a few times, it wasn't exactly a revelation to me. The fact that it affirms some of the rules I already live by and talk about - like taking intelligent risks and planning to adapt - is what helped me in this case. These guys are uber-successful and I was able to come up with some very similar actionable tips for readers, so that made me feel pretty good about my ability to provide knowledge and value to potential clients.

How It Could Help You: I know this post is about becoming an entrepreneur, but if that truly isn't an option for you, at least use this deck to start thinking about your career from an entrepreneurial perspective. And if you're halfway out the door and on the verge of making The Leap, maybe the deck can help you lay a solid foundation from which you can spring into your 'breakout opportunity'.

Find a Mentor

How It Helped Me: I'd often heard that the entrepreneurial community was extremely generous, but I'm still stunned by just how accessible, honest, giving and helpful the entrepreneurs I've spoken to have been. One very successful person in particular - Michael Mattalo, who I'm lucky enough to call a mentor and friend - has been instrumental in helping me get my venture off the ground. I don't think I'd be in the position I'm in today or writing this post if it weren't for his guidance and generosity. We're talking about an insanely busy man who has multiple businesses and a family who still found the time to meet with me for a few vital cups of early morning coffee.

Even other people in the Internet marketing industry who I've only had email or social contact with have been amazing (I'm looking at you Mackenzie Fogelson, Dan Shure, Ross Hudgens and Cyrus Shepard). A kind word of encouragement can go a really long way when you're just starting out.

I can only hope that one day, somebody thinks of me as a successful entrepreneur so I can return the favour and help them realize the dream of running their own business.

How It Could Help You: Chances are you know a successful entrepreneur. Even if it's just a friend of a friend, you can ask for an introduction and this person will still probably help you out. That's how the entrepreneurial community rolls. If you can't find anybody within your circle, consider joining local trade or business groups within the industry you'd like to enter. The more people you meet, the more opportunity you'll have to meet somebody who can help you.

Once you've found the right person, make sure you value and respect any time that they set aside for you. Be organized, punctual, and know what you want to talk about ahead of any meeting. Also understand that a mentor isn't going to make your decisions or tell you what to do. They'll offer a guiding perspective and the rest is up to you.

Be Confident and Trust Your Skills

How It Helped Me: I'm a confident guy and I know I can write, but quitting my job and going all-in on my skills was daunting. I know that my skills are in demand and definitely good enough that people would pay to have them, so I truly do believe I can build and grow this company.

My poker background has helped me launch a business in more ways than one, and that's true in this case as well. On the felt, you have to trust your instincts and believe that your skills will help you win in the long run (even when you lose in the short term). 

It might sound cliche, but believing in yourself is the first step toward success.

How It Could Help You: The same way it helped me. If you don't believe your skills (or idea if it isn't a service-based business) are good enough, then you probably shouldn't start a business. But if you know you have a great skill and can turn it into a commodity, now is the time, and you should do it. Don't wait or you'll kick yourself. If you're good at something, show people how it can bring them value and they'll pay for it.

Understand and Embrace the Risk

How It Helped Me: Again with the poker, but it really is relevant. I understand risk better than most, which means I'm also less afraid of it than most people. 

Another thing I know is that I'm not going to do anything truly great unless there's some sort of risk involved. For me, it was never the risk of quitting my job that scared me, it was simply whether or not it was the correct decision. That's what risk is about. If an intelligent risk doesn't work out, it doesn't make it a bad risk - it's just an intelligent risk that didn't work out.

How It Could Help You: This one depends on a lot of factors. By nature, some people are big risk takers, and others are completely risk-averse (if you're one of these, you may not want to launch your own business unless you have a rolodex of clients in hand). Sometimes risk is situationally dependent; if you just started a family, it might not be the best time to start a business (or maybe it is, it could depend on other unavailable factors). The point is, only you truly understand whether a risk is intelligent or not, and only you can embrace it.

One thing is for sure, though - if you aren't ready to embrace risk and everything that goes with it, don't do it until you're ready to hug that risk and hold on tight.

 Entrepreneurs Ready, Set, Go!

So there it is - all of the things that lead me to making The Leap, and some insight as to how my experiences might be able to help you with your journey. Whether you plan on sticking with a career or trying to launch your own business, a little bit of the entrepreneurial spirit will enhance your chance of success and provide you with new and exciting opportunities you'd never expect.