How to Make the Move from Unhappy Employee to Successful Entrepreneur

Bio: Dmitrii Kustov is the founder of Regex SEO. He was born in Russia and immigrated to the United States after completing dual degrees in Applied Mathematics for IT Engineering and  Translatology& Linguistics. As the Marketing Director at Regex SEO, Dmitrii’s blend of technical and marketing expertise offers unique value to their clients.

In 2015, I found myself increasingly frustrated with my full-time employment. I was working for a small digital marketing company that was going nowhere. The company was stagnant and for most of the employees, there was no opportunity for professional growth within the organization. After a series of discussions with management, it was clear that no changes would be forthcoming. I was faced with two choices: find a new job or create one.

I decided that I wanted to be in control of my own destiny. I took a leap and started my own digital marketing firm, Regex SEO. Looking back, I’m glad I didn’t know how difficult the journey would be. Now that the company has grown into a stable business with 15 employees, it’s a lot easier to see what worked and what I could have done better.

If you’ve got the entrepreneurial bug, but aren’t convinced you should make the transition from your full-time situation, these are my experiences and recommendations for making the leap.

Find your “why”

When considering entrepreneurship, the first thing you need to determine is why you want to start a business. You’ll need a powerful “why” to sustain you through the difficulties of creating a business. Many times your “why” will become the foundation of your business. Well, my why was stupid -- “why not”. I thought if those guys could make it, then I will surely be able to make it, because I see how bad they run the company. And, as I mentioned, I didn’t really know how difficult it would be. But luckily with a bit of persistence and finding the right people, it worked out.

Note: If money is your main motivation, you should probably consider sticking with traditional employment. For most people, money isn’t a good long-term motivator and it won’t help you sustain your vision when things get tough. Even with a good amount of income, the kind of work and amount of work required can be overwhelming, as I would soon learn.

Understand the differences

With all the social media celebrities out there, it’s easy to get the idea that entrepreneurs can make money by working just a couple of hours a day from a chair by the beach. Anyone who has already started a business knows that’s laughable to the point of being delusional.

The fact is, most people underestimate what it takes to make a new business successful. I made that same mistake. I thought with my background and experience, it would be fairly easy to set up shop and start bringing clients on board. Oh, how wrong I was. It took two years of working 16+ hour days, plenty of sweat and maybe a couple of tears to get the business in a stable condition. Even with the business being more stable, I rarely work fewer than 12 hours every day.

As a new entrepreneur, you’ll need to be prepared to put in a lot of time and energy for the foreseeable future. This is something you should discuss in-depth with your loved ones to make sure everyone is on board since this decision will affect them as well. Being an entrepreneur is never going to be a nine to five gig.

Test the waters

In the excitement of starting your own business, it can be tempting to leap straight into your new venture and leave your unsatisfying job behind. That is almost always a mistake. You need to do enough market research on your business to be sure you’ve got a viable product and that there’s sufficient demand for it in the market.

As we all know, the survival statistics for small businesses are dismal. Only one in five small businesses will make it past the five-year mark. Now, I’m not saying that you should wait five years before quitting, but testing your idea as a side hustle while keeping your full-time job will allow you to confirm that the business is feasible before you terminate your employment.

Working your business as a side hustle while keeping your full-time job has other benefits. It will help you get comfortable with being uncomfortable. Late nights and work-filled weekends are what entrepreneurial life is all about. Coming to terms with that while you still have a day job can really help you decide how committed you are before you reach the point of no return.

Note: Don’t try to double dip by working on your business while you’re actively at your current job. It’s a bit unethical and it could lead to severe consequences, including termination. There have even been cases where legal action was taken against such offenders. Your employer is paying you to work for their business, not your own.

Plan your transition

When venturing out on your own, you’ll be responsible for a lot of the things that your current employer does for you. Think employment taxes, health insurance, and retirement planning, to name a few. In addition, unless you have a lot of capital to pour into the business at the outset, you’ll also be doing most of the initial work yourself, including sales, marketing, business development, customer service, accounting, logistics, etc. The list goes on and on and on and on.

I recommend setting a goal that you want your business to achieve before you consider leaving your job. Having a hard target will take the emotion out of the decision and ensure your business is producing income before you make the leap. Perhaps you want to hit a certain sales volume for three consecutive months or sign up a certain number of clients. Whatever it is, it should give you a clear milestone to work towards before you make the move to full-time self-employment.

You’ll also want to consider the timing of your exit from your current job. Is there a time that makes sense as a natural transition, such as the end of a quarter or the completion of a big project? Make sure to take into account the timing of any bonus payouts, retirement vesting timelines and the balance of any healthcare or childcare savings accounts when considering your date for giving notice.


Being a business owner is all about hustle. You can have the greatest product in the world, but if no one knows about it, your business is still going to fail. You have to be constantly hustling to get the word out about what you’re doing, make sales, fill orders and follow up with customers. Even when you’re extremely busy, you have to keep up with marketing and networking to grow your business. Getting your business in front of as many people in your target market as you can and having a consistent stream of incoming clients is the only way to grow your business and make it successful.

Deciding to work for yourself and launching a new business can be one of the most rewarding things you do, but it’s important to approach it with a clear understanding of what you’re getting into. With the right approach, you can achieve your dream of being a successful business owner and ensure you get to be your own boss indefinitely.

Making It

So what is the end point, what does success look like? It’s a bit different for everyone, I suppose. For some it can be making millions and actually only working two days a week on the beach, or selling a successful company and moving on to the next project. For me, I still like to be very hands on. I’ve stabilized my business and work with a good team that keeps the business growing and improving every year. There are two parts of success, I think.

The first part is the concrete, financial aspect. Your business is up and running, you can afford to keep the doors open and support yourself and a team of employees. Maybe there is even room for growth and a nice portrait of the beach hanging on your office wall. Basically, financial success and stability is a major goal for any business, no matter the size.

The second part is a kind of personal, achievement-oriented success. Did you meet the goal you set before you left your last job? Are you satisfied with the progress of your company? For me, this kind of success was the most important. Instead of being unsatisfied with my full-time job, I was able to come into work and feel like I was making progress, doing the kind of work that I actually wanted to do with people that shared the same vision.

No matter what version of success you’re chasing, you should keep looking for new opportunities to learn and grow your business and your entrepreneurial skills. Don’t stagnate just because you found a comfortable plateau and keep working towards new goals. That’s the key to going from an unhappy employee to a successful entrepreneur. Just like when you set a goal to meet before leaving a past job, keep setting and meeting goals. Before you know it, you may have made it many times over.

Are you thinking about making the leap? What’s holding you back?

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