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Mid-Career Transitions

Posted on May 30, 2018
Image of woods where there are two paths to choose from

Mid-career transitions can be scary at best. Remember the Robert Frost poem, The Road Not Taken. Well, you may be standing at the precipice where two roads diverged in a yellow wood, so how do you choose which one to follow? The more travelled path may not be the best path for you, but the less traveled one, might make all the difference, but it could be fraught with obstacles or unforeseen road blocks. When you find yourself at a cross-roads, a diverging path– STOP – reassess before embarking down either of the paths before you.


Get into research mode and determine your skill sets. Here are a few steps to get you started:

  1. Make a list of the skills you believe you possess.
  2. Spend time on one or more of the many job sites out there and look at any position in your industry that you might be interested in applying for now, or down the road, and look for additional skills you possess, but you didn’t write down on your initial list.
  3. Now look at positions on an industry or segment of your current industry that interests you and you might consider moving toward – the path less traveled… and make a list of the additional skills you possess. Also make a separate list of those skills that you would need to learn or obtain to make such a move.
  4. Keep a copy of any job postings that sound interesting (whether you have all the skills or not).
  5. Now categorize your skills into skillsets – use the chart below as a general guide. 

Chart with generalized and specific skill sets

Now compare your skills with jobs that interest you on either path. Make a list of skills you possess and the skills you need to obtain. Clearly the positions in your currently industry will require less skill attainment and the positions outside your current industry will require more, potentially more education.

There is no checklist or chart to help you choose which path is best for you. Each decision is highly personal and situational. For example, it is much easier for a 35-year old single woman to make a career change than it is for a 35-year old single mother. Only you know and understand your limitations and responsibilities. However, the younger you are, the easier it is to make such life-changing decisions.

While I said, there are no checklists or charts, here are six questions to ask yourself as you stand in that yellow wood:

  1. Understand your finances – can you take a pay cut to shift into a new industry?
  2. Are there other people depending on you and your current income level?
  3. Can your ego handle a lessor title, which might be necessary when shifting industries?
  4. Are you in a place, personally, to devote time to learning new skills?
  5. Can you manage the few months of uncertainty or angst that will likely appear if you move into a new industry, take a lower paying position, or have to return to school, etc.?
  6. Can you live with your decision if you opt to take the easier, more comfortable path or will you always wonder about the one less traveled by?

Making a career transition can be scary, but it can also be highly rewarding. Unless you have obligations that will make it highly difficult, I recommend choosing the path less traveled because you won’t know about the potential benefits without stepping onto that path. And if you find it was the wrong path, you can always back-up and go back down the more familiar one.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.


Anne Converse Willkomm
Assistant Clinical Professor
Department Head of Graduate Studies
Goodwin College
Drexel University


Read the entire Robert Frost poem here.

Posted in professional-development-career-tips