Business Lifestyle
The Leap: From Employee to Self-Employed
August 8, 2014
, , , , ,

So you’re thinking about going into business for yourself? It’s one of the most rewarding feelings. The sense of ownership, accountability, and freedom are all worth it. However, making this jump is possibly the scariest thing you will ever do. Here are a few valid reasons to stop reading this article right now:

  • You are terrified of not knowing where your next paycheck will come from
  • Approaching people you don’t know makes you uncomfortable
  • You’re comfortable with your current job and lifestyle

All of these are perfectly understandable and acceptable reasons requiring no explanation to anyone.

However, if you want to change your lifestyle and are bold enough to challenge yourself, read on.

Being self-employed is NOT for everyone. I cannot stress this enough. Whether it’s the aforementioned constraints or something else, you need to decide what you want. Some of the required criteria:

  • You will have to work harder than you ever have before
  • Time management is an essential skill to have
  • You will have lonely days in the beginning

Kudos if you’re still interested.

I’m going to cover topics that were relevant in my journey with the hope that I can give you a sense of direction or how continue on the path of being self-employed. Obviously, all points cannot be covered when discussing this transition but I’ll highlight what I believe to be the most important.

The Challenges

Business vs. Hobby

Before you decide to walk into your bosses office and quit, you need to know where you’re going. Ideally, you would have started thinking about this before leaving the traditional “9 to 5” environment. Even better if you’ve already started conducting business to get a running start.

Whatever it is that you want to do, make sure it’s a business. Businesses are sustainable, scalable, and lead to growth. Hobbies usually yield low or inconsistent income, aren’t scalable, and the business model isn’t quite there for you to grow. This is why you test the waters while you’re employed. Keep a safety net there until you start to see potential in what you’re doing.

Once you define your business, start down the path of research to see if it’s a viable business.


You must be prepared to have an insane amount of drive, such that you almost forget to sleep because you’ve been so focused.  Losing track of time from working on your business cards or mapping out your next product is not uncommon. This is the routine in the first couple years of being self-employed. I remember being so exhausted at work to the point I thought I wouldn’t make it. 8 hours seems like eternity when you’ve had no sleep. On weekends, I would use up all the time I could because I knew during the week would be harder. Not very glamorous or exciting.

When to Leave

This is easily one of the most challenging of decisions when moving to self-employment. A few things to consider:

  • Are you in a position to support yourself financially if things don’t go according to plan?
  • Are you healthy? Paying for health insurance while self-employed can be difficult so make sure you use any benefits you may have before you leave.
  • Do you have a support system or friends and family that will support you emotionally and if need be, financially (either with gifts or loans)?

A great indicator that I use when I worked in corporate was how it affected my energy and demeanor. If I started to become more irritable, my patience level dropped, or I really didn’t love doing the work, that was the sign for me to go. I would always give the job a chance but I’ve come to the conclusion that I’m happier working for myself.

Saying Farewell

If at all possible, try to salvage any relationships with coworkers and/or your supervisors as they may support your step towards being an entrepreneur. Some people live vicariously through the self-employed. Whatever their reasons for not pursuing it, they love to see others doing it. I still keep in touch with a CEO who fully supported my decision to leave his company. It wasn’t the company or the people in it, I just had to leave. If you can relate to this, then make sure you follow a procedure of courtesy. Give your two weeks notice but also talk to you boss and extend your services. Start your networking and sales immediately!

Lone Wolf

Get used to being alone. You’ll probably partake in most of the following by yourself:

  • Eating
  • Attending networking events
  • Entertainment

Yes my friend, you will get to know the real you very well. Your character will be tested to every degree and you will find out exactly what you’re made of.  If you depend on others to have an enjoyable time, then you probably shouldn’t be an entrepreneur — never too late to make a change though!

The Rewards


When I walked away from corporate, understanding that I had full control of my time was so hard for me to grasp. It really doesn’t hit you until about 4 to 5 months in. You wake up and realize you can do what you want. Hopefully it involves the growth of your business, but nonetheless, you are free. You can stay up as late as you want and organize your day to fit your work habits. I usually work better at night so I get most of my work done from 10pm-2am. Then in the morning, I wake up at 10am and enjoy the day…repeat. It wasn’t always like this so don’t confuse that with my not working for it. It was definitely a process, but well worth it. If you have a family or children, of course this may vary, but you can still make it work. Just about finding a balance of your time. And always try to make your family a priority. Believe me when I tell you, you will find a way to make both work.

Recently, I took two trips to Paris, France, each for six weeks at a time. Let’s stop for a moment and think how that could’ve happened if I was working for someone else…it would’ve been nearly impossible (at least in the U.S.). These trips were for pleasure but I also worked while I was there. I found the nearest Starbucks and got to know the baristas very well! The only challenge was adjusting to the timezone difference but that’s minor in comparison to being in France. Great things came out of these trips: love and new business. In my opinion, time is the invaluable element that cannot be bought.

Positive Energy

My energy level and the positive energy I give off is extremely important to me. I need it to be balanced and exuding from my being when people are near. When you work for yourself and you love what you’re doing, you experience feelings of accomplishment and success which make you happy. This is contagious.

You’re happy, which makes others happy, which makes you…well you get the idea.

Having a positive spirit allows you to focus on achievement and to keep moving forward or staying motivated. You need to be motivated to make it. No one will believe in you as much as YOU. When others lend you advice to go the safe route, your outlook is going to determine whether you succeed or fail. Stay positive at all costs.


I’m sure you’ve heard this before, but the money will come if you’re good at what you do and you enjoy doing it. People love good products and services and you’ve obviously found a niche to fill with yours. Although you will find yourself “bootstrapping” or making ends meet, it’s well worth it in the end. As mentioned above, this will define you. You will figure out ways to get through the struggle.

Conclusiong & Next Steps

Once you get on your way to self-employment, it is one of the most rewarding feelings. However, the work is never done. I’ve had my fair share of hardships and adversity but I remained focused on the goal. Constantly challenge yourself to grow. Seek mentors and other business-minded people to help you along the way. Learn how to raise your prices and when. Read as much as possible on blogs and in books. Below, I have included some resources that have helped me along the way. Feel free to email me if you have any specific questions.

Books I recommend reading:

Sites I recommend visiting regularly:

Financial tools:

Project management:


Workshops & Seminars

I am planning to host a few workshops and seminars this Fall. If you are interested or want more information outside of what is in this article please feel free to sign up on the mailing list using the form below. I will not be sending you anything else except information regarding the workshops. Otherwise you can contact me directly:

Workshop Mailing List

About author

Vaughn Dabney

Related items

/ You might like these posts as well


Whew! I’ve Been Busy Building

An interview I did with my good friend Marlon Aver...

Read more
Screen Shot 2018-11-07 at 21.08.31

The 9-5 Solution: Interview

So you’re thinking about going into business...

Read more

FreshBooks #imakealiving Breakfast Panel!

I will on the #imakealiving panel with FreshBooks ...

Read more

There are 2 comments

  • Sageer says:

    Very interesting read. It’s good to get the perspective of someone who has taken that leap from a conventional job to a more personal professional path.

    I find myself in a position where I’ve left my job because it just wasn’t financially viable and now I’ve been applying to 9-5 jobs but to be honest it doesn’t seem inspiring to get myself into that environment. I have been thinking of developing one of my many ideas into a business venture. However how do you sustain you financially when your working on your business without a steady source of income? Also when do you draw the line to determine that perhaps your business won’t take flight. I am interested to know how you overcame these obstacles.

    Very nice post though. Thought provoking

    • mrdabneywp says:

      Hey Sageer,

      Thanks for reading! Sustaining yourself while working on a new business is a challenge for every entrepreneur. In my post I mention this, however in your case, you left your job and the idea of 9-5 just doesn’t inspire you. You clearly belong on the side of entrepreneurs my friend. For me, I started acquiring clients while at my current job so it was a bit easier. It may be that you just need to get a small part-time gig to bring some money in…I know it’s not desirable but being an entrepreneur is about humility just as much as it is being a proud business owner. No easy task to be uncomfortable at a job you don’t like, but think of it as a stepping stone. Or if you have people around you that can help support you for a little while, ask for help. But do so in a manner that doesn’t take advantage of the situation. Hopefully that helps a little.

  • Leave a Reply

    Your email address will not be published.

    18 − = 11