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Why is making a radical career change so tough?

Is there anything as hard as trying to navigate a radical career change?

From the time we are barely walking, we are being groomed to land a fruitful career. School, internships and part-time jobs are all designed to prepare us for what we will one day call “our career.”

This doesn’t pose a problem unless you decide one day that your career is no longer the right one.

Swimming against the current

There is no built-in social structure to facilitate major changes in career direction. Doing so requires a willingness to go against the grain, to not buy into the concerns of family and friends, and the capacity to work through powerful emotions that seem to pull you back to the secure job you once knew.

The other day a coaching client reached out with this exact concern.

He hired me to make a transition towards a different kind of life.

His previous career was that of a corporate ladder-climber. He was wildly successful. However, he was burned out and hungry for a better experience of work and life.

The goal was to craft a job based on his skills and interests; a solopreneur lifestyle that yielded income, joy, and a clear sense contribution. A full lifestyle redesign.

This was his decision and came out through several long coaching conversations and the client’s introspection after having a few months away from work to decompress.

The problem

A few months into his lifestyle design project, he got cold feet.

He worried that he was pursuing the wrong goal, that what he really wanted was to get back on the corporate “fast-track.“ The solution seemed to be, “let me just figure out how to run along the corporate fast-track while enjoying it and not getting stressed.”

My response was:

“Just relax and don’t jump to conclusions. See how it feels when you are actively working on your new business and creating a new lifestyle. If you have recurring and deep-rooted insights that you should return to your previous career, by all means, listen to those signals.

On the other hand, you might discover that the impulse to throw out the baby (your dream) with the bathwater (your past experience and future expectations) is just that, an impulse.”

Not every impulse requires a response.

This impulse, to rush back to the safer confines of the familiar life, is a common experience for anyone who is seeking to design their ideal lifestyle and vocation. Such re-imagination is bound to kick up a lot of emotional muck, including a healthy dose of insecurity (along with fear, guilt and yes, even boredom).

What happens when you get insecure?

Whenever I get insecure, I want to get a solid grip on the familiar, the safe and the secure (duh!). Just like when I was a kid learning how to swim, I would lunge towards the life-preserver impulsively. Eventually, I learned to ignore this impulse and trust my arms and legs to keep me afloat.

When my client got insecure (and redesigning one’s life will tend to do that) he wanted to retreat to the safe confines of the career environment he knew all too well, even though that environment was full of stress and no longer fit his values.

It was an impulsive move and a natural one. We all want to be safe and safety can be found through any number of places.

Three common safe havens are:

  1. Financial security.

  2. Recognition.

  3. Familiar environments.

My client was feeling a tremendous impulse to run back to his previous career, as it fulfilled all three of these safe havens.

It’s worth exploring these safe havens, as they aren’t nearly as “safe” as you would think.

Financial Security

Money matters. Though the specific amount you require to be happy is probably far less than you think. When you get insecure, you will become money conscious and price sensitive. If you are looking to transition your career, and start feeling anxious, the salary prospects (and certainty of income) of a familiar job can loom large. A sure-thing corporate salary will start to feel much better than the uncertainty of a new venture.You will find yourself being pulled back into the orbit of your past line of work.


Recognition is just as important as money.

I learned this first hand as a manager in the high tech industry. While my team members all appreciated bonuses, I was amazed by the degree to which top performers cared even more about being sincerely recognized and valued for their work.When we feel insecure, we gravitate towards environments where we feel appreciated and have confidence in our ability to perform.This recognition can be found in the safe confines of a previous line of work.

Familiar Environments Familiar environments are boring unless you are feeling nervous. Then, they become safe havens. It’s in a familiar environment that you know the rules and how to play the game. It’s like having a home court advantage. If you are feeling insecure about a career transition, you are going to feel like you should stick to familiar people, places and things. This can be a real monkey wrench for anyone trying to redesign their lifestyle. What can we do about it? Radically changing your career and lifestyle is hard. I’ve done it and still work through occasional (though increasingly rare) hunger pangs of a secure income, familiar environment and built-in recognition that comes from seeing the rungs I’ve climbed on the corporate ladder. It’s also tough to figure out what you want, to look at the hazy mist of the future and plot a course into the unknown. It’s even more challenging to make it happen.

The first step, however, is to strive for internal clarity. Figure out your answer to the “what” questions. It’s a crucial starting point. What do you want your life to be like? What career has meaning for you? What impact do you wish to make on the world? What learning curves are you excited to climb? Etc. If you don’t know the answers. Relax, you are in good company. All you can ever do is take your best guess based on how you feel in the moment. Find a quiet environment and a calm inner space from which to explore your answers to these questions. Then, as the mind is fickle and tends to forget, write down your answers so you can reference your thoughts the next time you feel nervous about how things are going for you. Remind yourself of the life you are creating, why it matters to you and how you can serve the world as a result. Passion alone isn’t enough. We need a deeper purpose and meaning to our work and lives.

The good thing about insecurity is that while it’s the trigger for wanting to give up on a dream, it’s a fickle emotion that flees at the very moment you get busy working on something that matters to you. So let’s get to work.


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