Career Reinvention Journal—There’s a Process, But It’s Messy

The decision to say goodbye to a role, firm, or industry and find a new way to apply your skills and accumulated wisdom is nontrivial. Career reinvention is hard work, filled with ambiguity and risks. And for those who undertake and sustain their career reinvention initiatives, it often proves to be one of the most powerful, liberating, and educational experiences of their lives. Of course, the operative word is “sustain.”

In contrast to mounting a job search campaign, career reinvention is several orders of magnitude more complicated.

In my role as coach, I guide individuals through the wilderness helping them search for the right “next” in their professional lives. And while there’s a process, it’s most definitely messier than you might imagine. Conditioning yourself to keep going in spite of the bumps, obstacles, and occasional switchbacks is essential.

The Six Steps to Career Reinvention

In years of coaching around career reinvention, every individual works through (in their own way) a six-step process that looks like this:

Determination—Is career reinvention right for me?
Self-Discovery—How do my history and life experiences combine to serve me in a new career?
Exploration—Casting a wide net in search of options that fit my abilities/interests/marketability
Experimentation—Proving or disproving the viability of the idea (abilities/interests/marketability)
Preparation—What the transition process must be from today’s reality to my new career.
Launch—Hitting the “Go” button

There’s no escaping the steps; however, if you were to create a process map for career reinvention, you would see a fair amount of iteration between the exploration and experimentation steps. This is the messy middle of the career reinvention process, and for some, it’s great fun and great learning, and for others, it’s great pain.

The Early Ideas are Often Non-Starters

Most (not all) individuals embark on a career reinvention process driven by a sense that they must do something different with their time and abilities. Long-time corporate warriors need to escape and experienced public servants long for a taste of professional life in a different arena—often one with a lot more flexibility and upside potential.

Some individuals bring ideas to the table, and after pausing momentarily to engage in some essential self-discovery/self-assessment, those ideas are eligible for exploration. Unfortunately, many of the ideas are hobbies that rent space in people’s minds as fantasy businesses.

I never dismiss those ideas, and indeed, some prove to be workable. However, most fail the marketability test. They’re nice ideas with no viable means of supporting anyone.

After those initial ideas are exhausted, we’re starting from scratch.

The Hard Work of Ideation, Exploration, and Experimentation

For any aspiring career reinventor who hits a dry well on converting a hobby into a vocation (read: most), the reality of staring at a blank canvas is daunting. As a coach, this is where the early work in self-discovery pays tremendous dividends.

Armed with ideas and insights on an individual’s superpowers and the details of their backstories, it’s possible to begin generating ideas. Of course the rule of “good ideas” looms large here. “If you want to generate a good idea, you need to generate a lot of ideas.”

We use every tool we can to build a list of suspect ideas, and inevitably, there’s a list of raw thoughts that require some filtering. Remember, our goal is to turn a few ideas into exploratory activities, and eventually something that merits developing an actual experiment to test for size, fit, and marketability.

Excitement and Frustration as You Work on Idea Generation

This process is both exciting and frustrating for the career reinventor.

It’s exciting for the options it identifies. I love observing as individuals begin to recognize the ocean of potential opportunities out there for them. For those who have been stuck in a career slot for a long time, it’s liberating to recognize their skills and accumulated wisdom can open other doors and new paths.

And then, it’s frustrating, because the typically diverse list of options seems daunting and even overwhelming. In most cases working with the individual, we can whittle the list of choices down to some that fit reasonably into the “Let’s Explore in More Detail” category. The balance of the ideas move to the parking lot.

Move Quickly from Ideation to Exploration

It’s imperative for sustaining momentum to kick into the exploration phase as early as possible. I encourage individuals to engage in both secondary (web searching) and primary research (site visits, interviews) as part of idea exploration. What seems intriguing on a web site often loses its luster when you visit or talk with someone immersed in this prospective vocation.

Armed with ample notes and impressions, we explore the findings together and define new areas of exploration, or, if it seems potentially viable, we set up an experiment to test out the idea. From working in a business to volunteering to attending courses or training sessions, the experiments are intended to offer proof the idea meets the individual’s interests and abilities. If so, we spend quality time assessing the final component: marketability.

Reality Check—You Will Iterate Between Exploration and Experimentation

While you might get lucky and hit on the idea that matches up perfectly with your skills, interests, and passes the marketability filter right away, don’t count on it. Chances are you will need to iterate multiple times with multiple ideas before finding one you are willing to commit to for this next stage of your career.

If the career reinvention process was like a marathon, you’ve hit that point where your mind suggests it might be OK to quit. Some individuals do stop here for a variety of reasons. Others silence that voice in their minds, focus on the step in front of them and keep moving.

Part of my role at this point is striving to keep the aspiring career reinventor in discovery mode. Identifying an area that doesn’t fit is a great learning outcome. While it might feel like a failure, I view it as one more success on a long journey. Checking an option off the list helps bring clarity to the path ahead. After all, much of strategy is about choosing what you won’t do.

Career Reinvention Happens on an Unpredictable Schedule

The other messy element of the career reinvention process is the lack of ability to predict how long this will take. It might be months, but chances are it’s a year or more and sometimes longer.

Most people are working a day job while navigating this process. For those with the luxury to focus solely on this process, it moves considerably faster.

For everyone, a consistent cadence of work is required to shrink the time-to-results. Much like a physical fitness program, thinking about or wishing your way to fitness aren’t options. Career reinvention takes time in the grind.

The Bottom-Line for Now:

If you’ve reached the point where you know you must do something different with your career, that’s great. It’s time to take action. Just be realistic about the upcoming journey. There’s a process, but it will get messy before it resolves.