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10 Failures of Transitioning form Employee to Entrepreneur.

November 04, 202320 min read

"You have to see failure as the beginning and the middle, but never entertain it as an end." - Jessica Herrin, founder and CEO of Stella & Dot

Failure Focus

Why failure? First let's look at how failure is defined. Failure means to not meet our expected outcome or miss the conditions of a requirement. In looking at the definition, failure is easy to accomplish. Actually we fail all the time. Some failures we simply shrug off as “oh well”. And other failures push us to the brink of madness and contemplating of ending it all! But who sets the bar for these failures? Or better stated, who is setting the outcomes or requirements and what are the real consequences of not meeting them? Usually the who is us and the requirements or outcomes set are also defined by us or are default set by society. And we either adopted the social setting or did not negotiate or modify the requirement or expected outcome to really meet our unique needs. With all of that, let's look at why failure can be leveraged to our advantage.

Failure when unexamined can cause us extreme mental and emotional pain. And you will hear me say this over and over again, pain is a powerful teacher. We need pain sometimes to tell us when something is wrong and failure is a very prominent and powerful pain professor that helps us examine our lives to help us get on track with what really fulfills us. Pain as a teacher can help us navigate the complicated waters of life so that we learn from our experiences and are able to set better directions. Our main objective here is to keep failure in its proper perspective through being mindful of its definition and adjusting our requirements or outcomes as needed. We must minimize the pain point from failure while directing more energy to our rebound from failure. To meet this shift in paradigm from how we view the pain of failure, lets review some of the failures that often accompany us when we newly set out on the journey to entrepreneurship.

10 Failures of Transitioning from Employee to Entrepreneur

Failure #1 No Strategy

Some of us fail at transitioning from employee to entrepreneur when we have no strategy. A lot of us think that you should just make a leap of faith and burn your boat! Now this may work for some people, but for many of us we need a plan. When you have children or a partner who depends on the consistency of your income, mental state and emotional stability (at least to some degree), it's better to have a plan. There is an old adage that says, when you fail to plan you plan to fail. Some of the most successful people will tell you that things go a bit better when they are planned out. This does not mean that everything will go smoothly just because you plan but having a plan can help you smooth the often rough waters of transitioning out of an employee role into the role of owner.

Failure #2 Burning Your Boat

Failure #2 Burning Your Boat

Wait a minute, we need to think twice before we burn our boats. Some folks feel like this is my only choice and failure is not an option. But as we are examining throughout this article failure is a part of the process of transitioning from employee to entrepreneur. We need to make sure we have, not only a plan A but a plan B through Z! Why?  Because in this time where society is transitioning into a deeper and wider frontier of the information and technology age, which itself is fraught with uncertainty and horizons of things like automation and artificial intelligence, we need to have multiple plans in order to be flexible as a form of insurance for our survival; let alone our success. Some examples of burning our boat include, cussing out your boss and all of your fellow employees as you flip them the bird on your way out the door. Or telling all your family and friends that they can, "go to hell" for not giving you money or buying your first products for that new company you started. Sometimes we might have to reach back a bit for people and resources as we learn to navigate the shark infested waters of entrepreneurship and even if we never get back into the boat of employee, we may need a lifeline or two from that historical direction.

Failure #3 Replacing Your Salary

There are multiple opinions regarding replacing your income. Depending on where you are along your financial journey and your entrepreneur mindset, you may need to start slowly. The simple formula is to start transitioning out of full-time employment once you are able to sustain your net income. This formula ONLY works if you have multiple controls over other aspects of your operations. Like a partner who can cover the bills or a contingency fund for unexpected expenses. Or if you have over a year's salary saved up just for the purpose of covering operations when income from your business is lower than expected. If you have such controls, you can make at least a half break from full-time employment (working part-time as an employee while working full-time in your own business). However, part of the expanding of our mindset that's necessary for become a successful entrepreneur is thinking bigger. We must master thinking beyond our current status including or income. One of the goals of becoming an entrepreneur is to be able to have enough wealth to have the freedom to afford awesome life experiences. If we only make our current salary then why become an entrepreneur? We could just as well keep working for someone else with a guaranteed paycheck every one to two weeks that often has at least meager benefits attached. The idea of replacing one’s net income is for those of us who are desperately in need of breaking away from the monotony and imprisonment of working for someone else. Basically, if you can sustain your net income through your own entrepreneurial pursuits this is one option for getting out of jail quickly! However, I want you to think big (as the book implies); there’s magic in it. The goal is to replace three times your gross salary within a year, not just your net income. But we'll talk more about mindset later.

Failure #4 Going It Alone

Failure #4 Going It Alone

This is where many new entrepreneurs fail. Somehow the American Dream of owning our own company became some person that was represented as an island. Success does not happen in a vacuum and without a solid team or support system none of the successful people you admire would have made it that far. I had to figure this part out myself through consistent collaboration with my tribe/teammates. We are just better together even if it's just for emotional support, motivation, and a good old-fashioned butt kicking session. All of that is needed along the adventure to success as an entrepreneur. But what my teammates really do for me is provide a variety of skills that each of us benefits from tapping into. My friend and brother from another mother is the tech guru, one of my tribe mate sisters is the social media maven, and then there is my tribe sister who is a marketing master. Plus I have my talented friends and family members for things like publishing (self-published authors of multiple publications), legal advice (cause one of them is a lawyer), back up staffing because many of them are smart, multitalented, and willing to help and they are good at providing old fashioned inspiration because they are entrepreneurs and top executives with stories of support, failure, and triumph that allow me to learn and grow. Don’t even think you can go it alone.

Again, this is a HUUUGE failure boulder for us. Every one of us needs some type of team support. Learn how to collaborate your way to success. Most people do but somehow when they tell their story the part about all the folks behind the scenes helping them, gets lost in translation. I have spent many years on my spiritual path beating that old devil ego into submission and would always make myself give credit where credit was due. My team is my spine and I could not do it without them. That doesn’t mean that on the journey to fulfilling your dreams of owning a successful company that some people won’t leave or betray you. But maintain enough of your senses to know that new team members will also find you and if you want to succeed you will welcome them with open arms.

Failure #5 No R&D

Entering your chosen market place without researching and developing your product and/or service is like trying to run a marathon without conditioning yourself. You probably will be carried off in a stretcher within the first mile. You need to know what you are getting yourself into. Research the market and find out who and what your competition is doing. Also find out if there are tumbleweeds where your business competition ought to be. If you can’t find any thriving competition, that could be a really bad sign. Some people think, “Yay great for me! No one is doing what I’m doing. I should be a great success!” The truth is this. The collusion of social media and technology make almost everyone in the world separated by less than two degrees. If you can't find a single entrepreneur or company in your market, it probably means there are no customers for what you want to sell. If this is the case you are setting yourself up for a huge failure. If there are customers and you are the only one in your market you may still be setting yourself up for a huge failure. Why, you ask? Because there is no blueprint for what you are about to do. The journey you are embarking on has no pioneers and no foreparents. The great thing is you’ll be the first, the frightening thing is, you’ll be the first. The road that isn’t traveled is the toughest road to travel. You will have to fight, fail, hunt, slay, confront, and bare knuckle it to carve out a brand-new market share. All I can do is wish you well, brave soldier. You will blaze the trail for those of us who will follow in your footsteps. Good luck and Godspeed!

Failure #6 Not Having the Right Mindset

Failure #6 Not Having the Right Mindset

I was teaching about having the right mindset before I had the right one. I was a manager and leader many times over, I had started and failed at three different companies before I finally held on to Bellwether Network and when I began making more in my business than I was working for Nonprofits part time, I finally understood. I had always had an entrepreneurial spirit but I had yet to harness an entrepreneur’s mind. Yeah, yeah, I read the books, took the classes, paid for and followed mentors but I had to learn my own strengths and weaknesses the hard way as an employee and as an solopreneur. Then I had to figure out how to overcome them.

As an employee I was good at doing my job which made the company want to hold onto me. Leadership opportunities and other accommodations were made to keep me there and before I really committed to being an entrepreneur those things were attractive and provided an easier and less scary way to maintain operations and generate revenue. But as an entrepreneur I was building my own brand and reputation. I had to overcome my low wealth ceiling. I also had to develop self discipline (more on that later). I had a number of weaknesses to compensate for as an entrepreneur and they were very difficult to wrangle because I was such a good employee and philanthropist. Yes, philanthropist! I had a difficult time charging people what my consultation and expertise were worth. I gave away far more than I earned and I wondered why I couldn’t let go of my part time gigs! I had to get my mindset in order. I had to distance myself from wanting to love on and care for people and be objective enough to charge what the market would bear for my services. The spiritualist in me had to fall back on the fundamental Universal Laws that govern me (and NO it is NOT the law of attraction!) the law of Equipoise (Balance) and the law of Karma. In these laws we must balance thought, exchanges, perceptions, wills, opinions without also creating Karmic debt for ourselves or others. In business there is an intentional exchange and as a business owner I diminish the value of the service I provide and increase the 3rd dimensional karmic debt for my customers by requiring an imbalanced exchange. If I agree upon an exchange it should be as such for all similar services and the exchange should be made. Uncollected agreements burdens my customer with karmic debt and non cohesive prices devalue my offering and bring imbalance to my craft. Charge all what is fair equally and collect that which is agreed upon. This was a difficult lesson for me as an entrepreneur. Each one of us making a transition from employee to entrepreneur will find the individual adjustments that need to be made to our mind sets in order to succeed. The better you are (or were) as an employee the more difficult it will be to adjust your mindset to become successful as the boss of yourself and possibly others.

Failure #7 Fearing Failure

This is a huge mindset shift. The most successful entrepreneurs embrace and sometimes look forward to failure. Yes I said “look forward to it!” because the most successful entrepreneurs take calculated risks that either teach them great lessons from failure or provide great profit. We all learn from the pain of failure; things we never learn from the pride of success. Pain is a powerful teacher and humans seem to learn from professor pain better than any other guru! Now what we learn will determine whether or not we fail again in the same manner. But failure singularly is valuable to the expanding entrepreneur. It gives good fuel for future success, it provides a story for others on their journey, and the lessons are expensive and hard earned. Learn to embrace failure and the multiple lessons about finances, business, and most importantly yourself as an entrepreneur and journeyman on this life quest. It will be the most valuable tool you will ever use to leverage greater success.

Failure #8 No/Low Self Discipline

Failure #8 No/Low Self Discipline

This was huge for me! The last obstacle I needed to conquer before becoming a full time entrepreneur and boy was life up to the challenge. It threw at me grief over the death of a parent, a world rocked by the coronavirus, family and friend’s emergency health challenges, upsetting my apple cart of financial strategy for full time entrepreneurship, along with plummeting stocks, and oh so much more. The old saying goes, tell the universe what your plans are and watch it laugh at you! But, plan I did! I still had to learn to commit to that plan in spite of the tornados whizzing around me. I was still grieving from the death of my mom and my mentor (both died in the same month!) while flying here and there across the country to care for my relative and my best friend, both being cut on by doctors during the height of Covid -19 and still had to maintain my commitment to be financially ready to quit my benefits job (that’s when you are working primarily for health care and other non income benefits). My goal was to become a full time entrepreneur by the end of summer. My last nemesis was self discipline. I needed to create balance with my self discipline that allowed me to work on my business and marketing daily. I needed to do things like go to bed and get up at the same time, drink plenty of water and nutrients and exercise in order to maintain my physical health and energy until the marketplace opened again. Because part of my strategy was to leave my part time benefits job to stay on only as a contractor, this meant I would be without health care for about five months. I needed to be self disciplined or my plan could fail horribly! Covid-19 was a blessing and curse. It allowed me time at the tail end of my cross country caregiving to be in the house and sit face to face with my enemies; grief and lack of self discipline! I had to figure out a way to balance my desire for leisure time, work for my clients, work for my patients’ as a part time employee, while also developing a physical care regime that was habitual and sustainable. Amidst all this, I was dealing with life’s monkeys that were being thrown at all my wrenches. While I was also building the online products and social media marketing plan for my business. This was war! The peace treaty was healing and self-discipline.

Failure #9 No Work - Fun Life Balance

One of my weaknesses as an entrepreneur and employee is that I am a Work-a-holic. "Hi, my name is Jodi Luster and I am a work-a-holic. Say hi Jodi!" As an addictions counselor it’s sometimes helpful to relate to people with addictions but I also need to relate to the power of treatment and rehabilitation. Let me explain. I do not love work. I love people, solving problems, creating new systems and integrating technology. I just so happened to have found occupations that allow me to do these things as I work. So work becomes a habitual addiction. Well the problem with a habit is that we have a tendency to do it, even when we need not. For years as a result of my habits, I had no work life balance. And even when I began to work less and do more projects that were entrepreneurial or for my family or home, they were not purely fun things. Enjoyable (I find installing light fixtures, painting walls and rehabbing bathrooms enjoyable) but not fun! I had forgotten how to have fun. In fact I am still working on this one as I write this. I am over 50 years old and my fun investment is about 0.5. Creating a work life balance will allow you to maintain physical and mental endurance, motivation through inspiration, childlike wonder, a sense of adventure, and thus provide you with a sense of novelty towards your entrepreneurial pursuits. That is the secret sauce. Have some fun, even if you are like me and forgot what fun was, set yourself on a quest to figure it out and incorporate it into your weekly schedule. It will be the fuel for your passion and allow you to be innovative in your business so it never gets old for you or your customers.

Failure #10 Failure to Launch

Failure #10 Failure to Launch

Not only was this a pretty enjoyable movie, it is also the nemesis and dream killer of so many would-be entrepreneurs. This almost did me in as well. One of the services that my company performs is business establishment and that service happens all the time. Business establishment is a function of completing some forms whether paper or online and whala! You have a business according to the IRS. What I’m talking about is a failure to launch! So the statistics of over half the small businesses that start failing in the first five years has a lot to do with this. To launch a business is really code for letting your would-be customers know you exist. Some fancy businesses have launch parties, others have grand well executed marketing plans, and there are some niche businesses like my mom’s that only require old fashioned word of mouth. Well most businesses are no longer sustainable with word of mouth and no online presence. Yes there is always an exception, but if you are reading this you are probably not the exception! You need to launch. There needs to be a christening of the vessel that will take you from start to success. Any Joe Schmoe can start a business but it takes tactical planning, team work, along with some skin in the game to launch. Many of us suffer from the fear of other people’s opinions or one of the other failure facets listed above and this causes a failure to launch. We have an “If we build it, they will come” attitude propagated by the movie that made that line famous. In some cases this is true, if you have a truly spiritual business sometimes miracles happen and you will be provided a great start because perhaps your early success was part of some destiny thingy! But like they used to say in the network marketing company I was in, “What got you here won’t keep you here!” Marketing, branding, rebranding, online presence, social media, good content, nurturing customer relationships and lots of value add are all a part of the launch. If you want to succeed you must launch. Bon Voyage my friend!

Failure Finale

These are the 10 failures that new entrepreneurs can look forward to. But mastering our perspective is about reframing and repositioning ourselves so that the pain of failure becomes a pivot point and not a point of paralysis. As we evolve along the tiers of offering the world what we are great at, we will revisit these ten points over and over until we truly evolve into an extraordinary entrepreneur who will appear on the world stages teaching the lessons of our path to those who will follow in our footsteps. Until then we need to keep learning and changing while recording our story along the way. It is the record of what we accomplished that is most helpful to those who look up to us. Yes we all want the road to success to be made smoother and it is our openness to learn from the lessons of failure and those who have blazed the trail ahead of us that will determine how many pitfalls we encounter on our adventure. 

*For those who really want the support in creating their roadmap from entrepreneur to employee, sign up for our Get Out of Job course and we can be a part of getting your wondrous story to success underway. If you need more than a course, select one of our ongoing consulting packages and I will walk with you as far as I can, along your journey to becoming the entrepreneur you always dreamt you would be!


Employee to Entrepreneur checklist:

Here is a quick checklist to get you started with your move from working for someone else to working for yourself.

  • Get your why right (Read this article that helps with refining your why)

  • Get your transition strategy together.

  • Adjust your mindset. Use mentorship, books, blogs, and various sources to get into an entrepreneurial mindset.

  • Practice self discipline. Use a habit tracker similar to the one in our leadership journal, that helps you improve your focus and productivity in entrepreneurial projects.

  • Start building a team or network that will support you.

  • Leverage opportunities to take a risk. If you get fired, laid off or demoted, use that as motivation to transition more fully into your own company.

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