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Many people dream of ditching the 9-to-5 grind to pursue the freedom of entrepreneurship. They imagine a life with nobody to answer to, no one dictating when we start or end our day. They picture limitless earning potential and the ultimate prize: freedom.
Many dream of it, but not all take the leap. For me, that dream started in college. I’d spend hours in design class sketching logos and brainstorming company names, imagining what life would be like if I were in charge.
At 26 years old, with a toddler at home, barely enough money to make ends meet, and more fear than confidence, I made the leap. I quit my job as creative director for a small advertising agency in upstate New York and set up shop in an upstairs bedroom of the farmhouse we were renting.
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I was working for a man who treated his employees like animals. He had no respect, no compassion and no humility. He was impossible to work for. The timing wasn’t ideal; nothing about it was, but the toxic environment left me with no other choice. I quit and started my own boutique design shop. And what started as desperation became the foundation of a multi-million-dollar advertising agency.
Entrepreneurship starts with a spark; sometimes, it’s the dream of independence, and sometimes it’s a necessity. For me, it was both. The early days were brutal. My wife and I struggled to pay rent and keep the lights on, and there were moments when I questioned if I’d made a mistake. But those struggles lit a fire in me that I didn’t know I had.
Within months, I was so busy managing clients that I had to stop making sales calls. Just over a year into it, I hired my first part-time designer. We grew quickly, too quickly at times (more on that later), but I refused to let the daily challenges and many roadblocks stop our progress. Within a few short years, we went from helping mom-and-pop shops to running national campaigns for Fortune 500 companies.
Leaving the safety of a paycheck is not a decision you make lightly. For me, it was terrifying. There were sleepless nights spent worrying about how to pay bills, moments of doubt so strong they 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 destiny. The fear of the unknown and the financial stress actually fueled my drive.
The reasons people leave steady jobs vary, but the emotions are universal: anxiety, excitement and that nagging question, “What if this doesn’t work?” Maybe you’re thinking about taking the leap yourself, or maybe not. If you are, your reasons might be unique, but from talking with countless business owners and entrepreneurs, I’ve learned 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 my ideas were always the best, but I knew my ability to implement even a few of them was constrained by my boss. Once I went out on my own, my creativity flourished in everything, from the way I structured my business to how I developed advertising and marketing materials.
Related: 5 Ways to Get Real Freedom as a Business Owner (Without Surrendering Control)
Toxic work environments
Sometimes, poor leadership or an unbearable culture forces you to consider leaving. That was a major factor in my decision. If you’re dealing with a similar situation, take the time to think it through carefully. Understand what you’re doing, plan and ensure you have the financial foundation to make it work.
Unrealized potential
Feeling undervalued or stuck can push people toward creating something where their skills shine. I never knew I had a mind for business and finances until I started my own business. There’s nothing more gratifying than stretching yourself and realizing how much more you’re capable of.
Related: Why You Should Hire for Potential, Not Experience
Financial freedom
The idea of uncapped earning potential often outweighs the risks for ambitious entrepreneurs. But don’t let the appeal cloud your judgment. The failure rate for startup businesses is high.
Approximately 20% of new businesses fail within their first year. This rate increases over time, with about 50% failing by their fifth year and around 65% by 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 still don’t know how I managed to climb out of that hole. For my family, the key was keeping expenses low. We didn’t splurge; 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. Scaling up wasn’t just about hiring or increasing revenue; it was about staying true to my vision while adjusting to new challenges. Hiring the wrong person could set us back months. Losing a big client felt like a gut punch. 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 sustaining it is another story. The market shifts, competition grows, and suddenly, what worked before isn’t enough. For me, success came from staying curious, constantly innovating and improving our company culture and customer experience.
Related: I Quit! I’m Not Telling My Boss. How to Stop Quiet Quitting.
4 key steps to take before taking the leap
The decision to leave a job isn’t just about courage. It’s about planning. You need to appreciate what you’re jumping out of and know what you’re jumping into. Here are a few key steps:
1. Financial preparation: If I had to do it over again, I would’ve waited until I had a solid financial foundation. Make sure you have enough to cover personal expenses for 6–12 months. Assume it will take longer than you think to see a 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 backward from there. This approach will help you clearly define your offering.
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 struggled with the difficult task of firing my first employee, he said something that has stayed with me: “If this ever gets easy for you, it’s time to step away.” His empathy and wisdom left a lasting impression.
4. Control your growth: Many businesses fail because they grow too fast, stretching themselves too thin and letting down their existing customers. I learned early on to say no to new business when I couldn’t handle it. It wasn’t easy, but that kind of control and integrity built trust and became a key to growing my business the right way.
Related: 3 Things You Must Know If You Want to Build a Business That Lasts a Century and Beyond
Are you prepared? Is this for you?
No one is fully prepared for entrepreneurship. The 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’ll question everything. Self-doubt is inevitable, but it can also be a great motivator.
Entrepreneurship isn’t for everyone. It’s stressful, unpredictable and sometimes thankless. But for those who take the leap, it offers something extraordinary: the chance to build something meaningful. Looking back, I wouldn’t trade those struggles for anything. They taught me resilience, forced me to grow and gave me the freedom to live life on my terms. If you’re standing on the edge of this decision, know that it won’t be easy, but it will most likely be worth it.
