Written by Terry Ouimet

SIMPLE TAKEAWAY:  “I really believe this was a huge realization about myself that I wasn’t even aware of on the surface for most of my life and certainly not how it related to my job satisfaction or life satisfaction. -I was a creative.”

SIMPLE ACTION STEP:  Spend some time contemplating why you want to quit your job and start your own business. Write all the reasons down on paper, good bad or indifferent, and this will be the compass that points you in the right direction.

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“I hate my job,” “I want to make more money,” “I can’t stand my boss,” “I want to be my own boss,” “I’ve always had a dream to start my own business.” If you dread heading out the door every day to your life-sucking job, you are not alone.   Anna Robaton with CBS News.com MoneyWatch on March 31, 2017 reports that according to a recent Gallup survey of the country’s approximately 100 million full-time employees, 51 percent aren’t engaged at work — meaning they feel no real connection to their jobs, and thus they tend to do the bare minimum.

Another 16 percent are “actively disengaged” — they resent their jobs, tend to gripe to co-workers and drag down office morale as a result.


I was in this position myself and decided to take the leap into entrepreneurship. I think you will agree with me that there are many obstacles that exist between giving your two-week’s notice and running your own successful business, making it a stressful decision. Below I share my thought processes at the time and why I did it. I believe this will help you as you prepare to do the same thing.

Why do you want to become an entrepreneur and what is stopping you?

My Number One reason for leaving my job and starting my own business was that I didn’t want to live with regret because I was fearful.

Here were some other reasons that I decided to do it:

  • I was extremely unhappy in my job

  • Huge Realization about Self:I’m a bit of a creative so I need constant challenge and variety

  • How important is money anyway?

  • I saw a problem and a very personal need in the market and I came up with a solution

  • I had gained valuable skills and experiences in small business

  • My hopes and dreams

1. I didn’t want to live with regret because I was fearful

Although I knew starting a business was where my path was leading and the door was opening, uncertainty and fear were weighing heavily on me.  I would be giving up a very lucrative six figure income, but I didn’t want to get to the end of my life and regretfully say: “I should have done it, and could have done it, but I didn’t want to risk it. I was too afraid.”

It was a sobering exercise to fast forward to the end of my life to see what my future old or dying self would have to say about me being too fearful to step out of my comfort zone with no guarantees. This brought some clarity and perspective into my decision making process. Ever notice that Fear has a way of presenting the worst case scenario and reminding you of your failures, weaknesses and limitations?

Anyway, I remember the day we sold our expensive house and traded in my BMW for a Honda CRV. I was starting my own business as a fine-art oil painter.  It was a weird combination of sadness, freedom and anticipation but I was really doing it. I won this particular battle over fear, but I knew I would see my old enemy somewhere down the road. The thing is, if you have a wise plan, good ideas, determination, focus and discipline, I believe you can minimize  the fear associated with that risk and set yourself up for success.


2. I was extremely unhappy in my job – Although I was making more money than I ever thought possible, I hated my job. My boss was going through some issues and the office environment was very stressful. Entering into this sales job in the oil and gas industry I had gone from working for a Fortune 100 pharmaceutical company where everybody had starchy white collars, to a small family business where half the employees had been in jail, large biceps everywhere, tats and no HR department. I think I’ll stop here and cut the details short because I value my life, if you need more information email me .

I’ll always remember my first day, I walked in and the guy to the left was 6’3” with arms bigger than my legs, I couldn’t see his skin, just tattoos everywhere, a large tattooed man in my midst. Wearing his ankle bracelet from his prison work-release program he said, “welcome to the first day of school yo.”  I should have turned around and walked out but I figured I played pro hockey, I can handle this. I got to my desk across from him with nothing on it but a phone. I guess its sales, what more do you need right? No training program, no introduction, no meeting and as I said, no HR department, just prison rules, LOL.

Image credit John Volante, Unsplash

The next four years would provide some good times, plenty of money and “success” in terms of bank account numbers, sports car and large house, but also some real low times and a mind numbing monotony that was like a daily chore. Due to the nature of this industry, the job was a series of one problem after another. As Kevin Costner said in the movie Open Range, “Well you may not know this, but there’s things that gnaw at a man worse than dying.” I think our soul dies a slow death when we have to go to a job day in and day out that makes us miserable with only a ray of hope that one day things could be much better.

3. Huge Realization about Self…I’m a bit of a creative so I need constant challenge and variety. I’m an oil painter, they call it Plein-Air Painting or painting outdoors. Plein Air oil painting started as a mere hobby to help offset the stress of my sales job. It rapidly grew into a passion, and then an obsession and then a dream. Life is too short to settle I thought to myself. Is it too much to ask to go to work and bring value to other people while loving what I do ?  How important is money compared to living out my dream and using my passions and gifts?

Something that I learned over time was that if my need for new challenges, creative thinking and learning are not met, I get that pit in my stomach on Sunday night, dreading going to work Monday morning.  I realized the reason that I was able to survive 10 years in pharmaceutical sales was that I was promoted twice and entered into management training- plenty of opportunity for studying, learning and trying new things. This was a huge realization about myself that I wasn’t even aware of on the surface for most of my life and certainly not how it related to my job satisfaction or life satisfaction-I was a creative.  

I was feeling guilty and kind of ashamed that I got bored and disliked my jobs every few years. But the light bulb went on, this is how I’m wired and I need to embrace it and work with that strength not against it by putting myself in creative environments.

4. So one question is how important is money?  Yeah it’s important obviously but stated a better way, what will you endure to make a lot of it?  Would you rather make good money in a job that you hate, or be an entrepreneur in a job that you love with no promise of riches?  This was the exact dilemma that I faced before I made my decision to start my own business. I think money comes at a price no matter how you slice it, and making a lot of money always has a flip side. I felt anchored or trapped in my particular situation because of it, but at the root of that was FEAR.

The money was my security blanket, or so I thought. As a child I was wired to think that performance and love were intertwined, that success meant I was loved. I think they call it conditional love?  If I gave up the money, my self told me that it would be a stupid move that could result in failure and disgrace which means I am a bad person.

Image credit Sharon Mccutcheon, Unsplash

It goes without saying, every entrepreneur has to square off with Fear when you go out on your own. I knew it would be an uphill battle, but it would be my hill and my battle at least. Besides, what if I could actually make more money out on my own? We can have these perceived false barriers that really prevent us from fulfilling our ultimate calling and potential.

I worked for a Fortune 500 company in sales with an above average salary plus bonus, company car, cell phone and lunch money. Then I went from that to the scary prospect of working on 100% commission in sales for a small business. I never thought I would do such a “stupid” thing, but I at least tripled my income  . This was a necessary realization and step for me to even be able to contemplate being an entrepreneur. It gave me the confidence that I needed to go out on my own.

5. I saw a problem and a personal need in the market and I came up with a solutionI think sometimes you start a business because you want to utilize your skills and abilities and just do it your own way, or you hate your job, or you see other entrepreneurs doing it and you want a similar challenge or lifestyle. But I think another really good reason that will keep you charged up for the long run and give you a good shot at success is if you actually experience a problem in the marketplace yourself and then go out and solve that problem in a unique way, for a mass market and that is what I did. If you begin with this as your “WHY am I doing this?” then I believe you are on the right path to success in part because of the trust and credibility that you bring to the market.

My belief is that if your strategy is to create a unique product or service with laser-like focus for a niche that has been ignored a bit by the market leaders, and then you market and sell the heck out of that solution, this is a smart way to go and will position you for success in the beginning as well as keep you determined over the long haul.

Photo credit Evan Clark, Unsplash

With my second entrepreneurial idea, I created and designed a unique portable camping stool for people with chronic back pain. My years of ice hockey gave me a bad lower back and when I went out to the mountains to plein-air paint, the stool that I was sitting on that we all buy at Walmart or Amazon, was three aluminum poles and a strap of nylon. Not exactly comfortable for long term sitting for the backside and my privates were numb after 20 minutes.

I thought there must be other people like myself who could use a comfortable seat while enjoying their favorite outdoor activity, and why couldn’t I be the one to make it?  Boom!, beginning of business idea with credibility and passion behind it.

6. I gained valuable skills and experiences in small business -and it gave me the confidence that I needed to branch out on my own and believe that I could wrap my arms around it and do it. I think every entrepreneur should consider working in a small business for a few weeks or months before starting their own business. Why not with so much to gain? I learned about business processes, accounts receivable and payable, collecting on late invoices and how to handle customers over the phone, how to look at cash flow as if it were your own and make decisions, inventory management and so much more.

In this particular sales job I had, my manager always told me “I trust you, make decisions as if it were your money and your company.”  When you have that kind of freedom and responsibility, it’s very good practice for running your own company.

Remember, I started with only a phone on my desk and built up my own customer base, eventually bringing in millions of dollars of profit.

7. Hopes and dreamsIs it too much to ask to go to work every day and be good at what you do and actually like what you do? I don’t think so, and life is too short to not pursue this endeavor and that is in part why I was inspired to start my own business and rise to the challenge. If we can combine our skills, gifts, experiences and passions into a way to provide for our loved ones while at the same time serving our customers well and affecting their lives in a positive way, I count that as a blessing and no better way to spend 50–60 hours each week if that is my responsibility as a husband and father.

One dream I had when I was younger  was to play pro hockey and I was blessed to fulfill that dream. Another dream I have is to build my own successful business doing something I love, but also help people find a more satisfying job and live a more fulfilling life themselves.

We all have hopes and dreams, what is your dream job?   I think we should carefully contemplate the reasons why we want to be in business for ourselves; it has to be for the right reasons, which will be different for all of us. If you always keep your WHY at the center of things, you will be able to weather the storms of uncertainty, doubt, fear and problems that attempt to make you fail.

So back to my original question, Why do you want to become an entrepreneur and what is stopping you?

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