A good number of people I encounter, talk about doing something different in their careers. For those individuals who cultivate the courage to pursue career reinvention, there are stark differences in the thinking and behaviors between those who succeed and those who don’t. Here are my observations based on several years working with dozens of aspiring career reinventors.

4 Key Observations of Successful (and Unsuccessful) Career Reinventors

1. Ruthless Commitment

Reinventing your career is some of the best but most difficult work you’ll do in your life. Changing a job is challenging. Fundamentally re-architecting what you do, who you do it for, and how you do it amps up the level of difficulty exponentially.

Much like the athlete commits to training and the aspiring musician to practicing, successful career reinventors cultivate and display a single-minded determination to work on themselves. They have families and day jobs, yet they build the work of career invention into their lives, instead of just tacking it on to already overcrowded schedules. It sounds easy, but whether it’s training or career exploration, making the work part of your life means making hard decisions about what not to do. The PTA, weekly bowling league, annual fishing trip, and even non-essential workout classes must go at least temporarily, replaced by activities focused on career reinvention.

Unsuccessful career reinventors in my experience understand the concept of ruthless commitment but fail to live up to it. They treat the work of career reinvention as additive and fail to make the priority calls essential to freeing up time. Guess what gets pushed out to the future when too many activities are chasing too little time? After all, career reinvention work is abstract, and that social gathering will be good for you, right?

2. Tolerance for Ambiguity

A minority of career reinventors show up armed with clear direction, merely looking for support in developing and implementing a game-plan. The gross majority of aspiring career reinventors are driven by a strong desire to do something different, but they lack ideas or direction. The lack of “where” or “how” is overwhelming, and when faced with extreme ambiguity, it’s easy to push-back and revert to something we know, even if it’s not ideal.

In reality, those who succeed at career reinvention accept this uncomfortable state of ambiguity. They embrace the process and work diligently to both self-examine for interests and abilities as well as to look for options that combine abilities, interests, and the ever-important element of marketability. While clarity emerges over time, there’s often a long-period spent navigating unknowns in search of something that is hard to describe.

This work demands a person tune-in to himself/herself as well as grow comfortable casting a wide net in search of different ways to translate skills and interests into a vocation. I call these stages of the career reinvention process, exploration, and experimentation. Those who lack ruthless commitment fail to make it out of exploration.

The exploration phase—searching for candidate opportunities or vocations—demands elastic thinking built on an open mind. Those who fail tend to be those who immediately impose a negative filter on every idea. They lack a Beginner’s Mind and quickly shut down ideas based on pre-conceived notions and biases.

Alternatively, successful career reinventors operate with a frame of “How might I apply my talents and experience in new ways?” They tackle the work of secondary research with energy, and they seek out people in a particular arena of interest to learn more. While their initial hesitancy over a direction or vocation might be ultimately confirmed, in many cases, their open-mind plus new insights gained through research provide a fresh perspective.

At some time, it’s imperative to down-select to one or two options for more rigorous experimentation, just not at the front-end of the exploration process.

3. Comfort with Experimentation

Years ago, I read some advice from a successful fast-food operator that remains priceless. “If you think you want to start a hot dog or hamburger stand, take a job at one twenty miles away and find out if you like the work.

This same commitment applies to most any career reinvention process. Successful clients have taken on moonlighting opportunities and even late-career internships to explore different segments. Several clients fueled by their excitement for a direction offered their services on a volunteer basis to explore them in more detail. While this isn’t practical in all settings, and we never want to invite ethical issues to the situation, some form of immersion is advisable before leaping.

For several career reinvention coaching clients, the work of exploration and experimentation led to a surprising outcome. It turned out, their best next step involved redefining their current roles and framing them from a fresh perspective. Effectively, these individuals reinvented themselves in-place, a fascinating and positive outcome from the process.

4. Find Joy in Discovery

My last observation here is one that I’ve noticed repeatedly. The successful reinventors have fun with the work and find great joy in learning about new areas and opportunities where they might apply their skills. Instead of fear and uncertainty clouding the work, they find it exhilarating to consider making a deliberate career move on their terms. Searching and testing is less labor and more love.

The Bottom-Line for Now:

Career reinvention is a challenging process and not right for everyone. For many, a job change will meet their needs. However, if you are intent on finding that new sweet spot that leverages your accumulated wisdom while focusing on activities you are interested in (and that are marketable), it’s essential to commit, embrace the process, and have some fun. The outcome will pleasantly surprise you!

Art's Signature