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jeffkrehely

The Worst Time to Start Is Never

In 2007, I toyed with the idea of going back to school to get a master of social work. Growing up, I often thought I wanted to be a therapist, and getting an MSW was one path (and the fastest) toward that career. I applied to a few schools in DC, where I was living at the time, and got into all three.

Kayakers in some marshy grasses, with a lighthouse on the horizon.
Kayakers in the Provincetown Moors.

When it was time to send a deposit to officially enroll in one of the programs, I decided not to do it. Why? I thought I was too old and that I was starting too late. I had a full-time job doing LGBTQ work and a master of public policy degree–and a voice kept telling me that I’d made my choices and needed to live with them. 



I was 31 at the time, and for some reason I felt older then than I do now at 48. 


A recent column by Russ Finkelstein gave me a flashback to this moment of my life, and I’m not mad about it! It made me realize how much my thinking has changed–for the better, I think. 


In his column, Russ gives some great advice to people who are going through the ups and downs of a job search–and touches on people who think it’s too late to start something new and/or feel like others are too far ahead of them. He mentions recent college graduates who lament not taking advantage of internships, which, like my thinking at age 31, makes me glad I’m older. 


Some of my thinking 17 years ago was shaped by my relatively young age. I had been working in the policy field for almost 10 years–nearly a third of my entire life!–and fully 100% of my adult life. It seemed impossible to deviate from the path I was on since that path ran through such a large percentage of my life. Spending a couple of years doing something different was not an option. 


Fast forward to my mid-40s, when I was once again contemplating a change: moving from leading and running organizations as a full-time executive to helping others run organizations. Part of this plan involved consulting, but the biggest part was fulfilling my desire to get trained to be an executive coach and then building a portfolio of work around that role. I also wanted to make time to pursue my photography practice as well.


By my mid-40s I had a resume that had a lot more jobs on it than when I was 30. Granted, these jobs were all in the same general field of progressive nonprofits, think tanks, philanthropies, and advocacy organizations, but the breadth of my experience was so much greater in 2021 than in 2007. And taking a year to try this new thing didn’t seem that wild of an idea. After all, it was one year of a career that was then nearly 25 years old. In 2007 taking a few years off for an MSW seemed like a much bigger deal, because I’d only been working for 10 years. 


And, of course, by my mid-40s, I had more savings than I did in my early 30s. So I had a financial cushion to help me transition from the kind of full-time work I’d been doing to something else. 


That didn’t make the decision easy, to be honest. Even in my mid-40s I still feared making a change. I worried about money. I worried about giving up the career path I was on. I worried about losing my network, or at least seeing it shrink. I worried about failing as a coach once I was trained. I worried that no one but my mother would buy my photography. 


But I was clear that the path I was on was not satisfying and did not reflect how I wanted to be living or showing up in the world. That had been a consistent message twirling through my brain for many, many years (yes, going back to those months contemplating an MSW!). 


As I wrestled with the decision to make a jump toward something new, I kept coming back to that message. No matter how thoroughly I thought I talked myself out of making a change, that vision of who and what I wanted to be kept making itself known. I had to jump.


As Russ says, “It’s nothing to do with when you start. It’s about moving ahead so that you realize the person you want to become.” 


As a coach, I work with a lot of people who know that they’re not on the right path. Some are crystal clear about who and what they want to be. Others have a vague notion of what they’re being called to do. Regardless of how sharp their vision is, so many of them struggle with starting to move toward it. 


A lot of the work I do with these clients is helping them to see that they can move at their own pace toward the new thing. It’s not all or nothing. And it’s not about waiting for the perfect time, or obsessing on why you didn’t start sooner or having THE perfect plan. It’s just about starting.


In truth, we can spend hours, days, and weeks talking ourselves out of something–even things that really matter to us. Maybe especially things that really matter to us. Saying yes to the thing you want is terrifying! It forces us to be honest, and vulnerable. It might disrupt parts of our lives that we hoped were set.


But if a certain idea or vision keeps twirling through your brain, it’s worth listening to, and worth giving a shot.  

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