The Good, Bad & Ugly of Becoming an Entrepreneur: What it Means for Money, Motivation & Making it Happen.

Image by Amanda Schutz

For most entrepreneurs the end goal is creating a sustainable business that combines expertise, flexibility, control and a steady revenue stream that allows you to work solely for yourself. This is a lot more possible than most think. I wrote an article a few weeks back on the new look of career stability, about how thinking outside of the 9-to-5 box and diversifying your revenue streams can put you in a better spot financially and professionally than relying on a steady paycheck from Company Q. There are so many small business development initiatives out there these days on a city, state, federal and individual level to help small business newbies navigate the tough terrain of going it alone. And people are subscribing to it, because these programs change lives and create jobs.

Hey, that’s me!
Under my umbrella of Career Transition fall two types of my ideal clients: those who want to find growth and success working for cool, creative companies, and those who want to BE the cool, creative companies that are growing and successful. And that’s what I do – help career changers in the creative field as well as budding, idea-toting entrepreneurs who are trying to build creative, socially-conscious small businesses like mine. For me, it’s been a fabulous, exciting, tumultuous and successful journey from desk to DBA, and I want others to be able to take the ride knowing they can succeed, and knowing they can do great work that inspires and changes their lives, and the lives of their clients and customers. That amazing ripple effect keeps the energy going like nothing I’ve ever seen…. it’s awesome.

I used to work for ‘The (Wo)Man’… 
It’s hard to get jazzed about recruiting – clients ignore you, candidates berate you, numbers haunt you in your sleep. I used to dream in spreadsheet format – I saw colored boxes full of bolded numbers, representing gross margin dollars, ROI, and operating income. I talked about P&L statements to my friends like they were something cool that anyone cared about. They’d respond to my otherwise useless knowledge by making obscene alter-meanings to all of my office-speak abbreviations. Granted, I LOVED balancing the books, setting the goals for the office, finding new and innovative ways to track them, and try to engage and motivate my team in the process. I knew every cent that went in and out of that branch, and I found it fascinating. But recruiting itself wasn’t that fascinating to me – running a business, and working with amazing creative people as my clients – that was the stuff that I loved! The ingredients were there, but the cake wasn’t quite tasting so good.

And I did it for awhile. And then I moved to New York. I worked in IT for a little bit. I talked to friends about servers and cloud computing, and it had the same effect as talking about P&Ls. “Cloud… like the white thing?”

I took a random Thursday off…
The company I had worked for for nearly 2 years was wavering back and forth with financial issues (our salaries had already been cut 6 months prior). I get a call from my coworker saying the board and our CEO suddenly and unexpectedly ALL resigned that day, and in the process decided it was in everyone’s best interest (particularly the investors who were tired of shoveling money into a black hole) to close the company that evening at midnight. So maybe it wouldn’t be that hard to leave a full time job after all, since I was basically being forced out within the next 12 hours.

Well something got resolved in the 11th hour and we didn’t close. In fact, we were sold several months later. I received an offer as one of the few employees asked to stay on board to transition over the company. They also dangled a nice fat bonus in my face. But I had checked out months ago, when I pieced together my big idea and decided I could set off on my own as a career coach and escape the annoying world of office politics. I spent $8000 for a certification that assured people on paper that I could do what I’d already been doing for several years. Now back at the office, not even the sweet scent of financial bribery could keep me in that desk and hold me back from my big idea. I wanted to leave. I wanted to leave so badly that I hired a therapist to tell me that I had to leave for my own health & welfare. I ideally wanted to get something else part time so I could still pay my rent and have 2 days a week to focus on my business. I had saved up maybe $5000, which goes nowhere in New York City, to pad myself for a few weeks while I got the business up and running.

The problem here is that in your average, to even less-than-average scenario, it takes well more than a few weeks to start up a sustainable business. It takes a few months to even begin to get traction, and in many cases a few years, if you make it, to truly reach a point of stability. Sure, there are always the lucky ones who land a great opportunity, a lucrative client, or a chance networking meeting that propels them far ahead of the norm, into early success-ville. But for the rest of us, we figure out a [somewhat] bulletproof game plan to survive the first 3 months. Then the next 3. Then the next 6. And then the next 12.

I ended up securing a freelance recruiting gig with a creative agency 2 days a week. Originally it was supposed to be more, but like things always do, the specs changed at the 11th hour and now I was looking at making half the money on a part time basis that I thought I’d be. And I gave my notice the day before. I had no clue how I would make it work, but I knew that I HAD to make it work. Because going back to my full time job, or getting another, was not an option. I had checked out of 9-to-5 ville for good, and like the stubborn ass I am, I refused to go back. More so, I had made up my mind to move forward, and at that point I wanted it so badly and was so excited about my decision and my newfound confidence, that I simply refused to fail or give up.

Some things I figured out by trial and error.
Like pricing. And other things I took from my education, and what was left to learn I asked other people to school me in or studied diligently to understand and put into practice. I decided to offer resume writing on a whim, in addition to career coaching, and then it took off. I charged half of what I’m charging now, and started to realize just how much I was undercharging several months later when people were so quick to buy. Once I came to realize that there was value there in my talents, it changed my thinking – I have something people need, so why not get paid for it?

I changed my logo three times in 6 months when I realized how corporate green grass waving in the wind looked. I changed my target market focus from everyone in the world who was changing careers, changing jobs or unemployed to job seekers in advertising, marketing, design & media, which was my background. Hyper-focusing like that made a HUGE difference. And much against Michael Gerber’s advice in “The E-Myth Revisited”, I eventually decided I liked working ON my business more than working IN my business. The answer? Work IN my business, by working ON other people’s businesses. But that developed later.

The company made $600 in its first real month of business…
I made just about the same the second. And from there on out, as my brand grew, my audience grew, and I narrowed my focus to a very select target audience – my revenue began to incrementally grow as well. I never had an unprofitable month. Pretty good for the first year. I remember being on a social media webinar with uber-guru George Kao where he talked about making $100 the first few months he was in his consulting business, and thinking “Well I got that guy beat… and he makes half a mill a year!” I’m not looking to make half a mill, I’m just looking to do good work that I love, and inspire and teach others to do good work that they love, so that they’ll continue the cycle and pay it forward.

Then by my second month, the part-time job I had ended unexpectedly when the agency realized they neither needed me, nor needed to continue overpaying me. I didn’t have a backup plan. I thought about rushing home to look for another side gig to support the little bit of business that was starting to come in. And then I decided to blow off the rest of the day and walk across the Brooklyn Bridge instead.

It was during that hot, sweaty trip when I decided that my life for the past two months, since deciding to go it alone, was completely saturated in anxiety and worry over money and growing my business in an unreasonable amount of time. It wasn’t working. My brain was fried from planning, re-planning, and backup planning, and I was only in month 2. So I tried something I’d never tried before: not worrying about the future, and riding it out on faith. It worked. Better than anything else. And eventually I trained myself to just not worry anymore, to problem solve and innovate in the moment, and most importantly, think big from a place of gratitude and abundance.

It’s been a fabulous ride for me as a business gal, a title I can trace back to my early recruiting days about 8 years ago. I’ve enjoyed a lot of success, and like anyone else, I’ve traipsed through my fair share of challenges, anxieties, and “WTF?!” moments. It’s not always sunshine and roses, or free vacation days running your own business – for you, for your relationships or your family. But people adjust. They start to like it when you stop complaining about hating your job.

In the end (or should say, the very early middle) there are three things I attribute to the success of my business:

  1. My left and right brain cooperating as a team, allowing me to love the rationality and process of business operations and continue to exist as the completely irrational creative person I am otherwise.
  2. A supportive hand-picked network of success-pushers, including my fiancé, my mentors and my colleagues.
  3. The absolute refusal to fail or give up. I want it that bad, that I will personally bend the odds in my favor.

That last one is important, and you will find that it, more than anything, will carry you through the tough times, the days when you doubt yourself and your abilities, the moments where you’re cursing everyone. Because entrepreneurs are born out of a passion to create something original and meaningful for ourselves and our society, and a rare willingness to do whatever it takes to the best of our abilities to bring that idea to manifestation. I love what former Yahoo! Chief Solutions Officer Tim Sanders said to Inc Magazine on the importance of confidence in becoming an entrepreneur:

“There’s enough to go around. There’s enough to share. The only way you’re going to believe this is through confidence, but when you believe there’s enough to go around and you share in that moment, you’re worth something.”

Because there IS enough to go around…
There are plenty of people to whom you have something of value, so long as you figure out where they are, how to tell them what it is, and why they need it. And it helps to be yourself in the process, as opposed to what you think sells, because people don’t just choose to buy products or services, they choose to work with people they like and trust.  Finding those people and making them your clients and customers is part of the reward.  And make no mistake, building a sustainable business is not easy, it’s not always fun, but one thing it IS, is rewarding.  It’s rewarding IF it’s truly what you want to do. And if it’s not, you will certainly find that out very early on. And then the rest of us who choose to keep traipsing forward in wavering confidence? We keep going, we keep dreaming, and we keep kicking our own asses, day after day after day. Because ass-kicking can be a great thing, a lucrative thing, the best thing you ever did… so long as you’re the one doing the kicking.

If you’re ready to kick some serious ass… let’s talk.

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2 Comments on "The Good, Bad & Ugly of Becoming an Entrepreneur: What it Means for Money, Motivation & Making it Happen."

12 years 9 months ago

I love this post! The advice not to worry about the future seems so apt, and yet incredibly difficult. I keep picturing utter disaster… even though I know that if anyone can do this freelancing thing, I can. The leap between me and successful people seems so big, it’s hard not to worry incessantly about how in the world I’m going to get there.

12 years 9 months ago

Thanks Natasha! It’s natural to be critical of ourselves that way, and try to mentally protect ourselves against failure by virtually placing ourselves there. But it’s important to envision the positive end as well! Thanks! What kind of freelancing do you do?