Eight Keys for Career Transition from Corporate to Entrepreneurship

A decade ago, at the age of 43, I made the boldest professional decision of my life. I decided to leave a safe and successful career at Kearney , a prestigious management consulting firm, to pursue my entrepreneurial dream that crystalized later in WALK .

My career transition was the result of a long process of self-reflection and look for my quest, although I did not necessarily think about it deliberately as career transition planning all the way through.

Here go my eight keys for a successful career transition from corporate to entrepreneurship. 

1.    Define Your North 

It is worthwhile to be clear on what are your interests and motivations, as well as your strengths and abilities.

• What is it that really turns you on?
• Which are those activities or moments when you feel / felt that everything was flowing effortlessly and you were enjoying it?
• What is it that you are really good at?

Sometimes it may help to go back in time and remember times from your childhood or adolescence to find those moments. It may also be helpful to ask some close friends or relatives who know you well and whose criteria you trust.

It would be great to identify your true passion or your “purpose” in life. In my experience, I found it difficult. I was not able to find “the solution”. It appeared to me as a static, unrealistic concept. So, I would encourage you to make an effort to identify your passion (or purpose), but do not get desperate if you do not find a clear response.

The minimum I would look for is to define a set of clear goals for the next chapter of your life (the definition of the duration and nature of such chapter can go all the way from 2 to 5 years and is entirely up to you). In defining those goals, try to start with “Why” before getting into the actual “What” and “How”. Why will give you an idea of the actual meaning of what you are looking for.

Defining your north is not an easy step. It may take time. In my case it took years. Any qualified help is welcomed here. I hired a good coach, used my business school's alumni career service, and read many books and essays including Business Model You (Tim Clark), Working Identity (Herminia Ibarra), What Color is Your Parachute? (Richard Bolles), How to Find Fulfilling Work (Roman Krznaric), How to Do What You Love (Paul Graham), and Status Anxiety (Alain de Botton).

2.    Embrace The Opportunity

The best opportunities arise when you are ready to take them. This does not always happen when you actively looking for them. Actually, often times when you are looking for things you are in a “control mode” which is not the best predisposition to address a good opportunity.

Ideally, you want the opportunity to come. When it comes, give room to your gut feeling to express itself. Not to say that you do not have to weight factors rationally (like compensation, upside, people involved, career progression opportunities, etc.) which are of course necessary to a good career transition, but it is critical that your “stomach” is up for it. It is the best indicator that it is something that can potentially be fulfilling for you.

3.    Ensure Financial Comfort

Financial comfort means something different for each person. Find your own definition: what do you need to move into the new space: maintaining your current income? Increasing it? Are you open to a reduction? How much? For how long?

The elements that determine your lifestyle may be jeopardized in a career transition from corporate to entrepreneurship, so better be clear about the non-negotiable: house mortgage, kids’ school tuition, eating outside and other leisure, retirement stability?

In my case, though many people consider my decision to switch careers as a brave one, I needed to have financial stability ensured and be able to maintain my family lifestyle unaltered for a few years as a pre-requisite to transition. Since I was moving to an entrepreneurial role, it required to have a good financial cushion to eventually face up to a few years with no income.

4.    Manage (Your Own And Others’) Expectations

Disappointment is the result of not having met a certain expectation. Changing expectation is the easiest way to avoid disappointment, and it is entirely within your control.

The first expectations that you need to manage are your own. Managing your own expectations has to do with reinforcing your self-esteem. In my experience, your self-esteem and your ego will be put on a severe test. Some people who looked high on you because of your prominent corporate title, may suddenly look at you differently. You need to be ready to live with that and remain strong.

Then come others’ expectations. If you are too concerned about many other people expectations, you will most probably be in trouble. I suggest focusing on managing the expectations of your closest ones. In my case it was simple: I knew I needed to have my wife on board of my career decision. I was ready to face other people’s challenges and discomfort with my decision (including family members and close friends), but would not do it without my wife’s full support.

Expectations management is important because a number of anxieties and fears will come for sure during the process of career transition, where uncertainty is the daily currency. If expectations have been properly managed you will be better ready to handle them.

In my view, stability in the personal / family front becomes crucial when transitioning careers.

5.    Be Clear About Your Values 

Values in this context are not an ethical or religious matter. They represent something you consider important enough to guide your decisions in the process. It is critical to be clear about who they are and honor them.

In my case, search for freedom and autonomy (coupled with a strong drive for having an impact through my own venture) were clearly at the heart of my career decision. I found myself often times challenged by the environment to honor those values. For example, a headhunter would call me to initiate a conversation for this top-notch position at a powerful corporation. Was I interested? Was I ready to prepare myself properly for the interview process? That would imply the consequent lost focus on my daily, non-revenue generating, dream-related activities. But on the other hand, was I really ready to let this opportunity go, and perhaps close the door for other ones to come through the same channel? If I was to honor my values, the answer was a clear “Yes”.

6.    Be Determined

There is no price without effort. There will be heavy winds and storms. Give yourself a full try for at least 18 months. Avoid getting distracted from your north and pursue it with faith, even though the evidence of success is not there yet.

7.    Charge Your Batteries

Changing careers requires A LOT of energy. This is very personal, but through my career transition I discovered the real importance of being fit, as a way to be energized to face the challenges at hand, to handle the stress that you feel at times, to help you maintain a positive outlook on things and be optimistic about yourself and about the future. It requires exercising, having a reasonable diet and keeping a healthy routine, which includes a reasonable dose of sleep.

8.    Enjoy The Journey

Last but not least: career transition can be huge fun and a unique and valuable learning experience.

In my case, it’s been one of the most powerful personal development and self-transforming experiences I’ve gone through. It has allowed me to grow as a leader and as a person, by expressing a better, more authentic version of myself.

In summary:

• Do your homework. A career transition from corporate to entrepreneurship involves an important decision and has consequences. Reflect and prepare for it. Manage your own expectations by visualizing in advance what are you getting into.
• Don’t wait to have all the answers, you’ll never have them. Once you feel reasonably equipped, give it a try.
• Don’t expect to have huge social approval, on the contrary. Make sure you feel comfortable occupying a contrarian stance for a while.
• Do something worthwhile, something your children would be proud of.
• Be patient, enjoy the journey!