Finding your path part 1: what it’s like to miss the mark

I’ve struggled to find my path in life. Prior to starting this blog, I moved from Washington, DC, to Colorado. I also stopped touring as a speaker, despite unexpected success and a 13 year career in the field. While writing this blog, I opened and quickly closed a leadership coaching practice, opened and continue to run a consultancy for speakers, raised capital for a business I decided not to pursue, took on a bunch of side projects, and finally, returned to school.

It’s been a long, strange, and difficult ride, and for the first time ever I feel like I’m on a true path as I work to become a therapist and meditation teacher. It’s reasonable for readers to ask, “Well, how does Jason know that? He’s had a decent number of false starts.” On one hand, I know that I’m on the right path – I haven’t felt this way before. But a far better answer is that as a writer and sometimes speaker, I work in public. I’ll prove it to you as you watch from afar.

This article is the first in a two part series. In it, we’ll discuss a phenomena that a lot of people fall victim to, including myself: being successful, but off your path. We’ll also talk about how to identify some of the subtle signs of missing the mark. In the next article, we’ll discuss practical steps that you can take to help find your path and start moving down it.

Two friends who got it right

Though many of my friends are successful, it’s C* and W* whose work I admire the most.1 Despite not knowing one another well, their paths are shockingly similar. Both became elementary school teachers after finishing undergrad in 2008.

After a few years in the classroom, C* was promoted to Vice Principal of his school. The following year he accepted a Principal position at a struggling school in his community. C* was tasked with turning the school around while concurrently completing his doctorate. He improved the school so dramatically that other districts routinely contact him for advice.

W*, after a few years in the classroom, co-founded one of the nation’s leading public charter schools. He was recently promoted to CEO where he is tasked with overseeing the school’s effectiveness and expansion.

Three signs you may be missing the mark

For years, C* and W* were complete enigmas to me. Like many people, I was obsessed with efficiency, success, status, leadership, influence, etc. C* and W* barely paid attention to that stuff, yet they were happier, more successful, more effective, and much less burnt out than I was. This of course, is the difference between being on your path and missing the mark.

Looking back, I realize that I missed a few critical warning signs that should have let me know I was on the wrong path. Unfortunately, catching these signs is trickier than it seems. In many success-oriented communities, they’re par for the course. If you’re in one of those communities, you kinda have to become a fish out of water, and it’s hard to understand what’s going on. A few of the most glaring signs that your heart is no longer in it:

1) You’re always on the precipice of being burnt out. Even when I had plenty of time to myself, I felt exhausted. This was in part because of the subtle but omnipresent sense of dread resting just below the surface. The truth is, I didn’t want to go through the falderal of doing the work I was doing. This is in sharp contrast to C* and W* who, despite working harder than I ever did, rarely burnt themselves out. To them, work was enlivening.

2) You’re spending a lot of time with self-help, personal/professional development, self-care  or motivation. C* and W* didn’t waste time with self-help, personal/professional development, or motivation because they didn’t need to. Since I was out of integrity, I needed a ton of resources just to keep myself going. In many cases, an obsession with motivation, efficiency, self-help, personal development, acknowledgement, self-care, etc. is an artifact of being on the wrong path. Of course, there’s a time and place for all of these things, particularly when you’re going against the grain to better the quality of your life.  But if personal development and its satellites are dominating large parts of your time and attention for extended periods, it’s a pretty clear sign that something is wrong.

A related indicator is being deeply driven by money, status, fame, and other forms of accolades. If you’re routinely seeking or in need of external validation, then there’s a very good chance that something has gone awry. One of my close friends is a book marketing consultant. When clients tell him that they want their book to become a best seller featured on Oprah, he responds by saying, “Ok, we can try to make that happen, but therapy is going to be a lot cheaper.”

3) In theory, you should be happy, but you’re not. While it seems like my success should have made me happy (and I certainly expected it to), it didn’t. Instead it inspired something a bit closer to self-loathing. Yes, I could find happiness elsewhere (and I often did), but doing so required work. C* and W* were entirely different. Though their success wasn’t nearly as flashy as mine and though they worked harder than I did, they were much, much happier.

Note: feeling like you should be happy, but not being happy, or enduring prolonged periods of apathy, ennui, or unhappiness can be symptoms of depression and other forms of inner unrest. As always, if you feel like you’ve been struggling with your mental health, I urge you to turn to a qualified mental health provider.

What do C* and W* understand that the rest of us don’t?

People immersed in entrepreneurship, leadership, thought leadership, sales, social media, and personal development, tend to believe that success is something that must be aimed for in order to achieve. This makes sense. The process of making sales calls, building funnels, cranking out content, split testing, engaging in humiliating levels of self-promotion, failure, rejection, chasing money and status, writing copy, covertly trying to impress your peers, etc. is so inherently meaningless that we need external motivation just to get out of bed. And again, I get it. I spent most of my professional life with these burdens.

To further complicate the matter, whenever we’re motivated by external validation, enough is never enough. At the beginning you’ll be excited just to have a client. Then you’ll be excited when a client pays for your flights. Then you’ll want first class flights. Then you’ll feel inferior for not flying private. I know that sounds crazy, but trust me.

C* and W* understand something that is lost on many people. They have figured out that if you take the time to do good work that you care about, especially in service of others, all that’s left is to consistently show up and do your best. For them, their stunning success and influence was never a target they cared much about; instead it’s an artifact of doing work that they find intrinsically meaningful. As far as I can tell, true success always works like that.


  1. A quick aside to discuss why I consider C* and W* uniquely successful. Though many people in my circle have achieved breathtaking things C* and W* stand out. Their work blatantly contributes to improving our world. It also provides an abundant (but not flashy) life for them and seems to bring notable amounts of joy and energy. While many of my other friends – especially the entrepreneurs – claim that their work is making the world a better place, it takes a lot of mental jujitsu for anyone to really believe it.

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