14 things I learned going from employee to entrepreneur

A 9-5 job is like a handrail. It can provide security, stability and hold you up, or rather, keep you from falling. It also can keep you tethered to the safe and familiar and not allow you to soar.

I let go of the handrail about a year and a half ago and wanted to share some things I learned along the way. But first, let me give you a little bit of history so you understand why I kept my grip so tight for most of my adult life.

I’ve been an employee since I was 15 years old and had my first “real” job working at a frozen yogurt/salad bar joint on Long Island. I made $2.50/hr. From then I had other jobs during college and the game changed once I graduated. Out in the “real world” I needed a “real job” especially living in NYC.

Even though I had studied psychology and always had an innate understanding of human behavior and was very intuitive, I never felt there was an option to do something on my own and I certainly didn’t know how I could use these skills, so I did what many people did. I got a job. At that age it almost didn’t matter what I did as I never even considered a “career”. You find a job and if you don’t like it, you find another one.

Part of it was that I didn’t know what I wanted to do, just what I was interested in…how to better myself to have the best possible experience of “being human” and inspire others in the process. To have an impact on others lives. I think in hindsight I wanted to figure out how to navigate life and then I’d be able to do “something” with it – and make money.

I had, what most would consider success. Promotions, raises, travel etc., but to my spirit, it was so off the mark. My life became a 9-5 façade of glamour working in the beauty industry. Yes, product development and marketing for the Big Name companies in NYC could be seen as very coveted jobs. While I loved living in NYC, I found myself choosing vacations that took me to holistic retreats in exotic locations in Mexico and Hawaii. This felt more like “me”. But how could I leave this career after so many years and start over? Seemed impossible and I felt trapped.

I never felt like I had an option.

Things shifted for me when I got laid off from a large company that was restructuring and I found myself unemployed. Around the same time I got offered to work for a start-up in California, a place I had dreamed of moving to. It was more money than I had ever made and I would get to live in Laguna Beach. How could I say no? Two weeks after I flew out to CA for an interview, I shipped my stuff and got on a plane with my cat for a new adventure in CA. I got a taste of what entrepreneurial life was like.

I was running a small company that was well funded and I got to hire (outsource) all the elements to launch a new product line. I had freedom and a lofty paycheck. Um, this is not your typical entrepreneurial situation, is it? No and of course it didn’t last. Due to internal conflict within the company the product didn’t get launched and I once again found myself unemployed.

But this time it was different. I knew if I was going to get a job again and earn anything close to what I was making, it was going to be in a big company, with a big title and a lot of responsibility. And that was where the problem lie…I was not the same person, having had my taste of freedom and didn’t want to lose that. I never wanted to go back to the 9-5 grind of 6-hour meetings and mandatory outings.

Over the years, I had a few other jobs in my industry but started to hear about something called life coaching which really sparked my interest. I resonated with the idea of starting where you are and moving into what you want to create in the future, rather than digging, diving and dwelling in the past.

I made the move back to NY after living in CA for 4 years. Work was not steady and I had a job offer that would enable me to work at home most of the time, which felt like a huge benefit. I could pretend I was working for myself while still getting a bi-weekly paycheck. I decided to get my life coaching certification while working at a job managing a spa in the Hamptons, which was another dream of mine. Got the certificate and had a few clients find me but I honestly had no idea what to do.

How do I get clients?

How will people find me?

I continued working full time and coached part time. I never really talked about being a coach and didn’t promote myself. Through on-line forums I got some clients but just felt like I couldn’t and didn’t want to do to what seemed to be required to have an on-line business. Spending 75% of your time marketing yourself and hardly any time using your talents, training and expertise.

One day when I was tired of feeling like I failed I decided I wasn’t going to be a coach and I would find another way to use my skills, talent and intuition. I didn’t expect what came next.

Huge relief!

When you’ve felt you failed at something that you never really put effort in the first place, there is big relief when you let it go. Soon after I made that decision, the idea came to me to create an on-line forum for people interested in consciousness and having a platform to share information.

The site was going to feature interviews, articles, workshops, forums, etc. I spent a year creating it and a few thousand dollars to have the website developed. And then it was complete. Now what? A very familiar scenario after I completed my coach training, but now I another year and additional money invested.

While my friends and colleagues were very supportive and loved the idea, not one person said to me, how are you going to do this without help? I just assumed I could it all to start and as the revenue increased I will add a staff. What I soon realized was that by me managing the contributors, content, writing articles, finding artwork, conducting interviews, etc., I would not have the time or energy to coach. That being an after thought bothered me.

So what did I do? Nothing. The site was live, but I continued to work my full time job and expected one day to wake up and magically figure it all out. That never happened. I wanted to coach and I wanted to differentiate myself from the millions of other coaches out there. Part of the challenge of having your own business or becoming an entrepreneur is setting yourself apart from the others out there doing similar work.

That’s when I discovered a modality to use with clients to give them the results they were looking for and set me apart from other coaches. Soon after I had the realization that the tool I thought I was looking for my clients was actually I was looking for myself. I enrolled in the Psych-K® basic training and my life changed forever. What Psych-K® enables you to do is identify and transform any limiting beliefs or stress triggers in your life. I quickly discovered the limiting beliefs I had about what was possible for me and was able to transform them.

For most of my career I felt like an imposter. I could look the part, play the part but my heart was not in it. I didn’t really care about climbing the ladder but was more concerned about figuring a way out. It really came to a head when I made the decision about what I was going to do, found a modality that would set me apart from others and yet had many doubts and fears about my ability to do it.

This was complete foreign territory for me. I was used to the security of a paycheck every two weeks and having a place to show up from 9-5 each day. The golden handcuffs as some would call it. It enabled me to have a comfortable lifestyle even though the hours I was actually at work I felt trapped, like I was squelching my talents by not being of service in the world doing what I love and helping others at the same time.

My spirit and soul would come alive after work and on weekends. There was a gnawing inside me – like the perpetual itch that needs scratching that will continue to persist and become more prevalent the more you ignore it. So on the one hand you have this yearning to do something meaningful that really gets you inspired and lit up and on the other hand there’s that paycheck and no vision in sight of how that cash is going to be replaced.

And then that day came. The day when I made the decision it was time and there was no going back. I wrote in a journal in January that I was going to somehow manage to go part time in my 9-5 in May and that I would be completely out by the end of the year. These target dates didn’t seem too scary and didn’t feel like I needed to figure it all out right away. I’ve come to experience that when you make a decision, things somehow magically take on energy and life of their own and things start showing up to guide you to the “how”.

In January, when the gang of 5 of us who worked in the satellite office in the Hamptons normally got our annual reviews, we were told that they going to close that location and consolidate everything to the NYC office. At first it was a shock and a little bit of fear, but I knew I’d figure out how to make it work. They agreed to let me continue working full time until the end of April and would let me stay on part time as a consultant until September. That ended up getting extended till the end of January. Pretty close to my May/December goals. I could never have imagined that it would have happened that way and with such ease.

When I started consulting part time, I was working from home which gave me flexibility of when and where I worked and enabled me to really start focusing on my business, further my Psych-Kâ training and get used to the idea of being self-employed. And let me tell you, that was not easy!

There are so many emotions that come up with taking the leap from employee to entrepreneur (or just plain ‘ol being self employed). It’s as if the security blanket (or handrail) has been pulled out from under you which is just an illusion that we’ve bought into and anyone who’s ever gotten laid off or fired from a job will tell you. There is also a prevalent belief system (at least for me) that you need to be a certain kind of person to be self-employed and I never even considered that I might be one of them.

Being a Psych-K® facilitator means I can identify limiting beliefs and transform them in to empowering ones that can actually support me rather than block me and sabotage my efforts. What shifts are actually the reactions, but the thoughts initially are habitual and keep making their presence known. I thought to myself…THIS is actually the work! It’s who you are being on a daily basis and how you are showing up.

One of the main things I quickly noticed was how my priorities changed. There were things I started to feel I could “do without” that didn’t feel like sacrifices to me. Many times in the past evenings after work I would find myself on-line shopping for things I didn’t need but for the excitement of getting something new because my daily work didn’t inspire me. As my work became more stimulating and satisfying to me, I discovered I wanted less and even found myself getting rid of extra stuff that I was not using. Money decisions are made differently. It becomes more important (such as when extra money shows up unexpectedly) to put it aside, rather than spend it on a spontaneous purchase.

One of the most important things to know in making this move from employee to entrepreneur is that you will be living with uncertainty. From week to week and month to month, nothing is guaranteed. You also are learning a new way of being, which can be both terrifying and confusing at the same time. Whereas before, you had a set time that you needed to be at work, so that pretty much dictated your wake-up and morning routine. You know you were going to be gone for x hours per day and then you had your evening routine.

This was one of the hardest realizations when I made the crossover from being a consultant and knowing I was putting in 4-5 hours a day, to having complete freedom over my time.

While I am still in the process of adjusting to this new life, I have put together a list of things I have learned thus far which may help someone else contemplating the move.

1. If you don’t know what you want, it will be that much harder to know when you have it. Be really clear on what you want and why you want it as you will need to remind yourself many times when the panic strikes in the middle of the night. Set reasonable goals to see your progress and know that every move forward is a success.

2. If you decide to go for it, make a pact with yourself that there is no turning back. This is not as easy as it sounds, but your future self will thank you.

3. You will need support. Even if it’s just that one friend who “gets it” that you can call up and talk you off the ledge, or can just ask “what do you think about this”?

4. Plan your time. Even if you have to make up appointments or take your laptop to your local café, schedule time “for work”. In the beginning you will be tempted to just wake up as you please, start work when you feel like it (unless of course you have meetings and/or clients) or maybe “I’ll take today off, because I can”. The danger is that minutes can turn into hours and the next thing you know it’s the end of the day and you haven’t made any real progress on your projects. It’s may not be that you need discipline, you just need a plan and a schedule.

5. Expect to doubt everything you are doing, think you are not cut out for this and fear that you’ll be sleeping in your car with your cat. You are going to have thoughts such as: why do you think you can do this? What if nobody shows up, purchases, subscribes, signs up, etc? How will I pay my rent in a month (3 months, 5 months) from now?

6. Examine and shift any beliefs about what is possible for you. What were the messages you received about what work meant for you and the way money can come to you? If there is guilt, fear, confidence or overwhelm issues, work with someone to transform them to remove any internal blocks to your success.

7. You won’t know what you are doing, so be easy on yourself. You don’t know what you know until you are actually out there realizing what you don’t know. There is a learning curve for everyone, enjoy the process of expanding your skills or getting help.