From Employee to Entrepreneur – The Reality

By Rebecca Bennett


If you are thinking about quitting your job…

The journey to becoming an entrepreneur is as scary as it is exciting. The emotional ride is not one that one can prepare for and will really test your inner strength and motivational stamina. Being one’s own boss comes with more pressure than working for another boss. If you are an entrepreneur in the making I hope you can find solace in my story that you are not the only one and take away tips you can use to get you through those slow days. If you are thinking about quitting your job to start your own business, here’s a taste of the reality, not to help you to decide whether you want to do it, but to prepare you for when you do make that jump.

The 7-Year Itch

I had worked in corporate America for essentially 10 years since I graduated college. I went into the workforce determined, aspirational and with great expectations that I could scale the corporate ladder to CEO. However, when I finally left, I came out of it frustrated, stressed and tired. Far from where I envisioned of being. I had worked across several industries for over 10 companies; big and small; private and public.

When the 7-year itch kicked in during that period in time, I decided I wanted to work for myself and run my own company. At first, the idea was it would be my second job, which I would hold down as a back-up to my main job in case one day I was laid off. I had made the cut in several lay-offs previously so was sensitive to the possibility. Once I built it up enough to replace my primary income, I would quit and go off on my own. Easier said than done.

So here’s what really happened

Within the first year I was slightly profitable, and the second year I could replace ¼ of my income and my third year I could replace ½ only working part time. It was when I reached that halfway marker that I knew, if I quit my job and replaced those hours with hours from my own business that I could replace my salary and maybe then some. But this is where I didn’t make the jump. It would take time to monetize those hours and I didn’t like that big question mark in the picture when I had a family to support, great benefits and honestly a great job at a reputable industry leader that anyone I spoke to said I would be stupid to give that up. So I didn’t.

At some point the scales start to tip

But my frustrations didn’t wane. As I grew more savvy about business from running my own and wearing all the hats of every function, I became extremely confident in myself and my abilities, to the point that I felt that my primary work was no longer challenging, no longer fulfilling, and career progress was a snail compared to the pace I was growing with my company. Any time I tried to step up and progress an initiative at my employer I got shut down. I felt like I had reached the top of the corporate mountain and had no where else to climb to. On the upside, I did become extremely efficient at time management and getting my work done, that it was a high time for accomplishments. But my accomplishments at work weren’t getting rewarded. It was becoming toxic, so I decided to actively look for another job. Two years later I landed that job and now was making way more money so that quitting for my business made even less sense. But it ended up not being my choice in the end. I eventually got laid off, for the first time ever, and was on my own. Something I had been preparing for financially for the last 3 years, but was not emotionally prepared for.

Oh, the freedom!

My immediate instinct was to look for another job just as I had always done before. But as I sat through interviews I found myself asking, is this what I really want? I have so much freedom now which I haven’t had in 10 years. I had no job constraints holding me back from what I really wanted to pursue, so why don’t I just focus on my business? So that’s exactly what I did.

In the first 2 weeks I secured an incoming rate of income that replaced my old salary from my old employer, but was slightly short of the most recent salary I had been making at my new employer. I was very happy with how quickly I bounced back on my feet. The outlook for my new life was looking up.

To get to the top you have to start at the bottom

But funny as it is, my confidence started to drain and I started to second guess myself. Would the rate I am bringing in be consistent enough from week to week to truly match what I was forecasting?

pixabay_free_frustrated product mgr_girl-1064659_640Even though I was actually working more hours a day on building my business, I felt like I was losing ground. I would listen to podcasts of entrepreneurs who are making it and realize that they knew way more than I did. These were my new competitors and they rattled off their accomplishments faster than I could blink and suddenly I felt like I was at the base of a mountain, rather than the peak, and I was looking up and thinking, how am I going to climb this thing? It’s so massive, where do I begin, which path should I take? My instinct has always been to diversify, or take more than one path at a time and see which one works out the best. But now there were too many choices, I was stuck still choosing.

Every time I took a step forward, it felt like I was in the same place. I would work hard all day and then look at the peak of the mountain and it looked no closer. On top of that my bank account was starting to decline.

The dilemma if work is your hobby

Since my business started out as a hobby and still is, it felt like that I was working on a hobby instead of actually bringing in more income. I had extreme guilt with my family about what I was working on, afraid that they would turn their backs when they saw all the days I was spending away from them amounted into nothing.

bigstock-punching-the-clock-394230Anytime I needed a break, I would turn to a hobby. But wait a second, wasn’t I just working on a hobby, so do I really deserve a break if I am just going from hobby to hobby? This would force me to keep working and not take breaks. It was an endless working cycle which was burning me out.

How is it that at work I could accomplish so much? I could do my work, run my business, manage our finances, do the groceries, take care of the dogs and still have energy to work out. And now I feel like I can barely get anything done and am afraid that one day I will forget to feed the dogs or pay a bill because I don’t have time. How is it I have more time on my hands, but feel like my business is actually running slower? I’ve even cut out putting on makeup and prepping my hair and I still feel like I have less time than before.

“Welcome to the life of an entrepreneur!”

If you are already an entrepreneur in the making you know what I am talking about. If you are thinking of quitting your job to start your own business, welcome to my reality. As glamorous as it sounds, there are a lot of hidden unknowns along the way to stress you out and second guess yourself. It is not for the faint of heart.

Getting Started and Staying Sane

Here are my recommendations to manage your day and squash all the worry.

Start with the money makers.

Your priority is to bring in money to sustain everything else. Focus on revenue generating activities first and foremost.


Breakdown your goals.

Breakdown your goals into to do lists, always having the bigger picture goal at the top so you can reassure yourself that you are working towards something worthwhile.



Prioritize your day the night before.

Select 1-3 things from your list of things to do. Always schedule less than you think you will achieve. As humans we have a tendency to over-schedule things and at the end of the day feel like we have barely made a dent in our to do list. So be sure to always make the day achievable.


Schedule breaks and me-time.

This is critically important to maintain your sanity and sustain your momentum. There is minimal value in pushing through a dry, burnt out brain where it takes twice the mental power and effort. You are better off walking away and getting some fresh air. I recommend moving and focusing your eyes off into the distance. A walk is great for this.


Stay social.

networking people

Working from home can become lonely very quickly. I highly recommend joining a few MeetUp groups or Mastermind groups that you can connect with a few times a week. As you go for walks in your neighborhood, look out for regulars and strike up a conversation with them. Hopefully one day you can turn it into a daily jog or dog walking activity you can do together. When your friends and family are far away, call them up to say “hi.” Ask them about their lives so you can pull away from yours and gain perspective.


Create structure for your day.

Studies have shown that humans operate better when they have some sort of structure to their day. Just like you were at work and got so much done, do the same for yourself but at home. Set up your routine in your calendar with pinging alerts 5 minutes before to remind you of what you should do next.


Focus on one thing at a time.

Multi-tasking is the road to not getting anything done. Progress will be slower so avoid this nasty habit by trying to catch yourself when you do it. Make an oath to yourself that when you do, you will do 10 push-ups every time. When you have a thought interrupt your work, write it down then go back to what you were doing.


Watch out for HALT signals.

Hungry, Angry, Lonely, Tired. If you find yourself in any of these states, it means break time. Take action immediately to get yourself out of the state as soon as possible. Eat frequently, about every 4 hours is recommended, watch a half hour comedy show or funniest home video clips, socialize or take a nap. You are your least productive when you are in one of these states, so the best thing you can do it to get through it as quickly as you can.


Get a coach.

For those of us who have tried these recommendations and still struggle, I recommend to hire a coach to help give you the daily dose of motivation and accountability you need. If it helps you get stuff done, then it’s worth the investment.

2 thoughts on “From Employee to Entrepreneur – The Reality

  1. Pingback: Podcast: Going "Beyond The Interview" & Leading in the Hard to Lead Areas of Life | LAUNCH!

  2. Pingback: Intro to LAUNCH! – Podcast Episode 1: Become Your Own Leader | LAUNCH!

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.