The Winding Path of Work

Society has come to a collective agreement over the past decade that you should not expect to spend your career with one employer. I’m not talking about whether one should strategically not do so for the sake of professional growth and/or financial advancement, but rather because such loyalty and security has fallen far out of favor. The people who continue to advocate for staying in one place are in a very tiny minority, like those advocating on behalf of the health benefits of cigarettes.


In contrast, the idea that you will have a career in a specific kind of role or industry has been pluckier. Many still hold fast to the belief that there is one kind of work they will be doing. To support this they gather all of their skills, training and network to bolster it. They’ve created a mighty professional silo tall, sturdy and fortified to weather any storm. Or, at least the more predictable ones that they can readily see– paying attention to be current on important technology and research, attending professional events where they meet and build relationships with their accomplished peers and perhaps taking on leadership roles to become a known voice in their industry.    

Then the unfathomable(s) happen:

  • You realize that you no longer enjoy the tasks associated with the kind of work.
  • Due to unseen circumstances more money has suddenly become the primary driver which requires that you do something very different.
  • New technology or systems come along and what was once so essential that needed to be done by an experienced human is no longer.
  • Your industry is dying overall.
  • A merger has taken place and at your level of pay and experience getting similar roles becomes elusive if not impossible.
  • Something occurs where you can no longer meet some of the demands of the work.
  • Something happens to your child, partner, older family members, etc. that requires a shift in schedule or geographic location that makes what you’ve been doing impossible.

The thing about the unfathomable is you can’t always plan, and even if you have time, the runway may well be short. Listening earlier to the signs that you are unhappy is always a good place to start, but many of these simply occur and we find ourselves reacting and feeling hopeless. 

When the unfathomable happened to me I realized that I was at a loss for words to get help and had no idea how I would begin to think about that change. So, I want to ease you into the simple truth that you are very likely going to switch it up and do something completely different professionally. I hear from people every day dealing with the unfathomable(s).

If you read me on occasion you know that my tendency is to write a list of questions and bullet point steps about how you deal with such a thing. However, I’ve decided to dedicate some space to feature the stories of folks who have made significant changes in careers from a range of careers to lots of different kinds of work and for a wide range of reasons.

As a regular part of my writing for the next few months I will be sharing the stories of individuals who have had to make this change and how they experienced the process itself. They are all on the other side, but having been through this once are better prepared than many of us to change to something else entirely if they are called to again. 

I currently have 30 people who have agreed to share their stories from across the country and around the world. I’ve worked with or coached all of them and reading their narratives will help you understand why I feel like I am pretty fortunate to do the work I do. They are all exceptional individuals, but so are you. They took risks, they felt fear and they were able to set some goals and achieve what they wanted in that next role even with obligations and constraints. 

I hope you learn from their myriad journeys and pick up what worked for them and gain the confidence to embrace the unknown.

Russ Finkelstein [] is the opposite of your High School Guidance Counselor.  A career coach, social entrepreneur, and advisor to founders, he is currently the Director of Coaching with the Roddenberry Fellowship, Coach-in-Residence with StartingBloc Fellowship, and a Co-Founder of Title8 a Legal Marketplace. He was a founder of the noted careers website and was chosen as a Generation Z Influencer by LinkedIn.


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