Reinventing Yourself: From Employee To Entrepreneur

Are you thinking of starting your own company and being your own boss? It’s the biggest trend in business today!
I have been working with a number of corporate employees who left the structure of the corporate world and struck out on their own. You leave behind the perks of the position: the administrative support,the title,the regular paycheck, favor of the freedom to be your own boss, to do things the way YOU think they should be done,to use your creativity. Among those who are successfully making this transition and excited in their new business one thing is clear:  Confidence and Self Trust are the cornerstones of their success.

When you (or someone you know) think about starting out on your own, is one of your first thoughts, “But what if I fail”?   (If so, you are in good company. A lot of people have that thought!) For example, before he came to work with me Luke had been laid off from a Fortune 500 company and spent many weeks exploring his options and going through the roller coaster of hope and disappointment on job interviews.
He considered starting his own company (actually he has always wanted to do this).   But he kept saying that the financial risk was too great. Upon further examination, his real issue was not the financial risk, per se, but a confidence block.

When he developed real confidence in himself, he came to trust his own resourcefulness. As he looked at his situation more objectively, he had confidence to believe that he could do something similar to what he had been doing, but do it even better on his own. He even got just a little bit angry, enough to make him prefer to invest in himself than place his destiny in the hands of other people he felt pretty certain did not have his best interest in mind. Within a few weeks an investor gave him $250k to start a mobile games company. (And, let me tell you, that kind of investment made him feel really confident!

All of the great companies, e.g. Google, Intel,HP, etc started off with a business plan that went through many iterations until they found what worked. Your mindset of confidence in yourself and perseverance is much more predictive of your future success than any particular “business plan” or idea.   If you have an idea and have always wanted to start your own business, or grow your current self employment into something bigger, you must have the right mindset.

Here are five tips to shift your thinking from fear to taking action and controlling your own destiny:

1. Be more rigorous and systematic in your thinking – Don’t allow yourself to stop at the first thought of “it will never work”.  Require yourself to think through how it has worked or not worked for other people, and what is similar and different/value-add about your initiatives.   See if you can start to determine whether your thoughts are “objectively true” or just what you tell yourself in your own mind. Test your assumptions against ‘facts’.

Be explicit about the assumptions you are making in terms of the viability of your ideas:  you will want to make sure that you have challenged your assumptions and they stand up against current trends and thinking more objective than yours.  The more you have done your research the more you will feel confident and “bulletproof” to other’s potential criticisms.  You must also cultivate the habit of perseverance and objective thinking in order to be successful in your own business.

2. Own your value. List out concretely how you have helped other people in your prior positions so that you can have conviction about the value you provide. Be sure to quantify the results and the ways you have helped other people. Ask others to provide you with feedback about the most positive ways you have impacted them.

3. Identify the doubt you have about failing and either Accept it or Accomplish whatever it will take to move beyond it. Try to specifically pinpoint what you think you’re lacking to make your next step work. Then, either figure out a way to work around that doubt (e.g., partner with someone who has the skills you need or, decide you don’t need the experience you thought you’d need to get started) or else commit to building the skill or trait you will need (like confidence or perseverance).   Make a plan, get a coach, whatever it takes.  (Another new resource you can use is Keith Ferrazzi’s new book “Who’s Got Your Back” to help you use your closest relationships to achieve what you want).

4. Network, brainstorm,  and mastermind regularly with other people you respect. Ask for feedback about your ideas. Be open and receptive to other’s input but also develop questions to ask yourself that will help you discern whether their (naysaying or overly optimistic) input is coming from their own worldview and has little bearing on your own possibilities. Consult with a financial advisor who will help you to be objective about the financial numbers.

5. Get honest with yourself. What are the real reasons you want to start your own business?   The reasons that will serve you the best in the long hours ahead are motivations of passion and a genuine desire to solve a specific problem that a lot of people are hungry to resolve.   If you are doing it to “prove” something to someone (or if you go into it worried you will fail to prove something to someone) then you are not following the recipe for success. Cultivate the self knowledge and trust your “gut” instincts.

imageIf you live in the NYC area, know this:   NYC wants to provide funding and resources to get new companies started! You are invited to attend the NYCStartUp on June 24 to hear what is available to you.  You will also find out if entrepreneurship is right for you and how to get started; hear the successes and mistakes of well known business owners (such as the head of,, Double Click) and hear from Joy Bauer of the Today Show, Robert Tuchman, etc.  You will also have the opportunity to join the Next Big Idea Contest with VCs and industry experts!.

If you have to give bad news…

You may find that you have to give ‘bad’ news in these times. It may be to an employee, a client, a contractor, a family member, etc.

If you have a tendency to put it off it is because it makes you feel uncomfortable (another deeper reason you might put it off is because having that difficult conversation activates for you a deeper concern about it having been your fault). If you have been putting it off because you don’t know exactly what to say, see below for some universals that will help you frame the conversation. (And If you have been putting it off because its a way of not feeling bad about yourself, then the idea is to make a plan to learn from your mistakes so you won’t have to put yourself in a situation again where you have to procrastinate to distance yourself from feeling bad about yourself!)

Some guidelines:
1) Say what you mean and mean what you say – Don’t be vague and indirect so that they have to try to figure out what you are saying. Be direct and clear. Say it in your utmost respectful tone.

2) “Match” then Move – Never just try to be pollyanna about it. Don’t try to move in right away with false reassurances or just present the rosy side of the picture – (you think these are intended for the other person but mostly they are intended to help you feel better.) The person is entitled to have disappointed or angry feelings about the news you are giving them. The first thing to do is to empathize with what they are feeling (“I can only imagine that this is very frustrating/disappointing for you…”) When you accurately reflect their feelings you have more credibility with them, then they are likely to be open to what you will say next that will try to help them move forward.

3) Contextualize – The recipient of the news will definitely be wondering “why” the events are unfolding the way they are – Give the reasons why, tell them how this decision was arrived at, contextualize your news in the the overall big picture, or provide a comparison to what’s going on in similar relevant contexts.

4) What will happen – Be very clear, simple, and concrete about exactly what will happen next – what you will do, what they can expect to happen, what they need to do, what logistical events will need to take place, etc.

5) Have a forward moving message – Have a message that you will tell yourself that will enable you to stay motivated. If you have a message about how and when things will get better then you can offer that. Pay more attention to the future picture you paint for yourself in your mind – Stay focused on it and keep moving towards making it true.

“The best way to predict the future…is to create it” Peter Drucker