• Jim Young

Don't Look Back ... But Don't Leave IT All Behind

Updated: Nov 11, 2019


It took a lot to get over that mountain...

Yesterday, June 25, 2019, was an important day for me. It marked the final day of a nearly 22 year career in IT. It was quite a ride, one that The Universe decided to recognize with me.


My career as a "techie" started with the infamous Y2K crisis. (Remember that??) I fondly recall being hired by a big, prestigious Boston law firm to help them lead their financial systems into the new millennium. I was secretly terrified because I wasn't trained in IT and only vaguely had the experience they wanted. A few months into the job, after I knew I was on stable ground, I asked my manager why he had hired me. (That seems bold, in hindsight.) His response, that he believed I had the "attitude and aptitude" to do the job, has stuck with me all these years. It continues to serve me well to remember that being positive and open to new ideas is a very successful strategy.


When the law firm was acquired in a merger I moved on to a startup. I was officially part of the Dotcom boom cycle! Alas, the demands of that job turned out to be a bad fit for me, so I moved on to another job a couple of years later - another law firm. I did great work, but again, the fit was wrong. On and on this cycle went, through various industries and companies of all sizes.


Then came the end - yesterday. As I finished up the final day of a contract as a "Senior IT Advisor", I felt a big old mix of emotions. In the past, I would've brushed these off and remained stoic. Instead I allowed myself to celebrate the accomplishments, recognize the relationships I gained, be touched by praise I received from colleagues, and look towards the excitement of my new career. I even made room for the sadness of leaving something so big behind.


Now, back to the whole Universe thing... I really believe that there are "coincidences" that we see that aren't accidental. If we're paying attention, there is something bigger than us that is in tune with what we're calling for. And it happened within 3 minutes of my drive home last night. I consciously thought to myself as I clicked on the radio that there was going to be a song that held meaning for me playing. Probably something about this big transition. The station I had been tuned to was playing a commercial. Since I was feeling nostalgic I hit preset #5 for the local classic rock station. Here's what was playing:

Don't Look Back Boston
Don't look back A new day is breakin' It's been too long since I felt this way I don't mind where I get taken The road is callin' Today is the day I can see It took so long to realize I'm much too strong Not to compromise Now I see what I am is holding me down I'll turn it around I finally see the dawn arrivin' I see beyond the road I'm drivin' Far away and left behind It's a new horizon and I'm awakin' now Oh I see myself in a brand new way The sun is shinin' The clouds are breakin' Cause I can't lose now, there's no game to play I can tell There's no more time left to criticize I've seen what I could not recognize Everything in my life was leading me on But I can be strong I finally see the dawn arrivin' I see beyond the road I'm drivin' Far away and left behind

Umm, seriously?!? Look at those lyrics again - how perfect are they? A few of them really stood out to me:

  • The road is callin', Today is the day - I mean, c'mon. I was literally driving on the road and it was the day I had taken the last step to move forward. Wow.

  • Now I see what I am is holding me down, I'll turn it around - For years I have held myself back with the self-limiting belief that I didn't have what it took to pursue a dream career. And I've decided not to hold myself down any longer. I have turned it around!

  • Cause I can't lose now, there's no game to play - Throughout my IT career I was playing a game defined by others, one that I hadn't even really wanted to play. I was forever doing what I thought I should do, just because I could. It never really fit. As I move my coaching business into a full-time career, I am no longer playing any games. I'm just being myself and loving the work I do immensely.

  • Everything in my life was leading me on, But I can be strong - I received a lot of adulation for the work I did. I was really good at it. I got raises, bonuses, promotions, recognition by family, friends and coworkers. The allure of that praise kept leading me on to do work that never truly felt right for me. It took a couple of decades, but I found the strength to trust in myself to do work that matters to me.

There's perhaps one line from this serendipitous song that I will take with a grain of salt. (Hey, The Universe isn't perfect!) The "Far away and left behind"line doesn't quite work for me. I gained a lot in my last career. I'd be a fool not to use the skills I honed in the complex crucible of the corporate world. Skills like deep listening, mentoring, strategic thinking, conflict management, project planning, visioning, and so many more will be so useful to my clients and me.


As a coach, I am beyond excited to help others find their Universe song. Or if they don't believe in my magic car radio, I at least want to help them find the courage to go after the dreams they are called towards. It's so worth it!


Having moved on, I won't look back wistfully or fearfully at my IT career. But I will occasionally peek to remember all that I gained from it.

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