Is entrepreneurship for you? Here's how to find out


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Many people dream removing the 9-to-5 wrangle to pursue freedom of enterprise. They imagine a life with no one to answer to, no one dictating when we start or end our day. They represent unlimited earning potential and the ultimate prize: freedom.

Many dream of it, but not everyone takes the plunge. For me, that dream began in college. I spent hours in design class sketching logos and company name ideas, imagining what life would be like if I was in charge.

At the age of 26, with a young child at home, little money to live on and more fear than faith, I took the plunge. I quit my job as a creative director for a small ad agency in upstate New York and set up shop in an upstairs bedroom in the farmhouse we were renting.

Related: 9 lessons that entrepreneurship will teach you

I worked for a man who treated his employees like animals. He lacked respect, compassion and humility. He was unable to work. The timing was not ideal; nothing about it was, but the toxic environment left me with no other choice. I quit and opened my own boutique design store. And what started as desperation became the foundation of a multi-million dollar advertising agency.

Entrepreneurship begins with a spark; sometimes, it is the dream of independenceand sometimes it is a necessity. For me it was both. The first few days were brutal. My wife and I struggled to pay the rent and keep the lights on, and there were times when I wondered if I had made a mistake. But those efforts ignited a fire in me that I didn't know I had.

Within a few months, I was so busy managing clients that I had to stop making sales calls. A little over a year into it, I hired my first part-time designer. We grew up fast, sometimes too fast (more on that later), but I refused to let go of the daily challenges and many obstacles in the way stop our progress. Within a few years, we went from helping mom and pop stores to running national campaigns for Fortune 500 companies.

Leaving the security of a payment is not a decision you take lightly. It was scary for me. There were sleepless nights spent worrying about how to pay the bills, moments of doubt so strong it made me sick to my stomach, and a constant feeling of walking a tightrope. But there was also something liberating about taking control of my own destiny. Fear of the unknown and financial stress actually fueled me.

The reasons why people leave stable jobs vary, but the emotions are universal: anxiety, excitement, and that nagging question, “What if this doesn't work out?” Maybe you're thinking of taking the plunge yourself, or maybe not. If you are, your reasons may be unique, but from talking to countless business owners and entrepreneurs, I've learned that these are some of the most common motivators:

Independence and creative freedom

The ability to make your own decisions and build something from scratch. I never believed that my ideas were always the best, but I knew that my ability to implement even some of them was limited by my boss. Once I went out on my own, mine creativity flourished in everything from how I structured my business to how I developed advertising and marketing materials.

Related: 5 Ways to Get True Freedom as a Business Owner (Without Surrendering Control)

Toxic work environments

Sometimes, poor leadership or a unbearable culture it forces you to consider leaving. This was a major factor in my decision. If you are dealing with a similar situation, take the time to think it through carefully. Understand what you are doing, plan and make sure you have the financial basis to make it work.

Unrealized potential

Feeling undervalued or stuck can drive people to create something where their skills shine. I never knew I had a mind for business and finance until I started my own business. There is nothing more enjoyable than lying down and realizing how much more you are capable of.

Related: Why you should hire for potential, not experience

Financial freedom

The idea of ​​untapped profit potential often outweighs the risks for ambitious entrepreneurs. But don't let the appeal cloud your judgment. The failure rate for start-ups is high.

Approximately 20% of new businesses fail within the first year. This norm increases over timewith about 50% failing in their fifth year and about 65% in their tenth year.

Starting a business brings financial uncertainty unlike anything most of us have experienced. You don't know when your next paycheck will come or if you'll even have one, and that uncertainty can be paralyzing.

I remember one night during my first year in business, staring at my P&L with no light at the end of the tunnel. To this day, I don't know how I managed to get out of that hole. For my family, the key was keeping expenses low. We do not brag; we survived. Every decision and every dollar had to count. It was exhausting, but it taught me discipline.

No one tells you how hard it is to grow a business. Growth was not just employment or income growth; it was about staying true to my vision while adapting to new challenges. Hiring the wrong person can set us back months. Losing a major client felt like a punch in the gut. But every misstep taught me something: how to hire better, diversify our client base, and lead a team without micromanaging.

The first taste of success is intoxicating, but keeping it is another story. The market changes, competition increases, and suddenly, what worked before is no longer enough. For me, success came from being curious, constantly innovating and improving our company culture and customer experience.

Related: I Surrender! I'm not telling my boss. How to stop leaving alone.

4 key steps to take before taking the leap

Deciding to quit a job isn't just about courage. It's about planning. You have to appreciate what you are jumping from and know what you are jumping into. Here are some key steps:

1. Financial preparation: If I had it to do over again, I would have waited until I had a solid financial footing. Make sure you have enough to cover personal expenses for 6-12 months. Guess it will take longer than you think to see steady income.

2. Market research: Know your audience and understand the problems your business solves. From my agency days to my speaking career, I've always asked myself, “What do I have that this industry absolutely needs?” Don't force it and don't fake it. If you really want to deliver something meaningful, start with the customer experience and work backwards from there. This approach will help you clearly define your offer.

3. Have a mentor: In the early days, I befriended a bank vice president who became an invaluable source of advice. He was always willing to take my call and guide me through challenges, whether it was employee relations or financial decisions. When I was faced with the difficult task of firing my first employee, he said something that has stuck with me: “If it ever gets easy, it's time to leave.” His empathy and wisdom left a lasting impression.

4. Check your growth: Many businesses fail because they grow too fast, becoming too lean and disappointing their existing customers. I learned early on to say no to new business when I couldn't afford it. It wasn't easy, but that kind of control and integrity built trust and became the key to growing my business the right way.

Related: 3 things you need to know if you want to build a business that lasts a century and beyond

Are you prepared? Is this for you?

No one is completely prepared for entrepreneurship. Reality is messy, unpredictable and often overwhelming. You'll wear every hat: sales, marketing, operations, HR – you'll do it all. Income will be unstable. Financial stress is real and you have to learn to live with it. You will question everything. Self-doubt is inevitable, but it can also be a great motivator.

Entrepreneurship is not for everyone. It's stressful, unpredictable and sometimes unforgiving. But for those who take the plunge, it offers something extraordinary: the opportunity to build something meaningful. Looking back, I wouldn't trade those battles for anything. They taught me resilience, forced me to grow, and gave me the freedom to live life on my terms. If you are on the verge of making this decision, know that it won't be easy, but it will most likely be worth it.



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