Two Career Roads Diverged, and I Cannot Decide

In 2014, I wrote a blog post titled “Two Roads Diverged in Your Career Path Woods…and You?” in which I played off of Robert Frost’s famous poem to look at how often we get hung up in life (and thus career) on the ins and outs of making that next step when sometimes all we need to do is just, well, make a step, any step.

I was once again pondering all this recently when I was speaking with a college assistance planner in regard to my daughter, who is about to enter high school. I was discussing how as parents, my wife and I were findings our heads collectively spinning when it came to all the hoops that supposedly needed to be jumped through, and all the boxes that supposedly needed to be checked, when it came to improving her chances amidst college rejection rates that seem to be at an all time high. “How many AP classes can she handle over the next 4 years?” “How many times will she need to take the ACT and SAT, and should she take SAT subject tests?” “By age 18, will she have mapped out her entire life plan and seen enough of the world so she can write some highly philosophical entry essay?”


Obviously, like many parents before us, we want what’s best for our daughter. We want to believe that we are giving her the best guidance and the best opportunities. And, yes, obviously, we are willing to get educated on what’s happening out there and get advice. But, what we’ve found is that there is a point where knowledge and advice can only go so far and you have to stop and ask, “What is our end goal, really?”

In other words, you have to stop chasing and start building.

Of course, you don’t reject all the advice and ignore all the hoops. Some of it is practical, a necessity, a fact of life (SAT scores do matter, for instance, especially if attending a selective college is important to you), but you carefully begin to pick and choose the path you want to follow based on who you are, not on what others say you have to be.

If you don’t, you will go crazy competing against a scale in which you will never measure up.

Naturally, as parenting usually does, all of this got me thinking about my own life and career path. How many times have I just been chasing instead of building?

Over the years, I’ve written about the “rat race”…the allure of it…the constant worry that you aren’t checking off all the right boxes, that the image you’ve built isn’t quite what it should be. We all fall victim to it at some point. We end up on this never ending cycle of playing “keep up” or “catch up”, and it seems like we have little control.

We seem to be living in a world that is a bit out of control.

Certainly I’ve seen this with my technical management clients. They think of personal branding as a mold or structure that they have to squeeze into in order to be “accepted”. In reality, usually what makes personal branding effective is someone who knows how to crack the mold a bit, so to speak.

It’s a frustrating place for those who’ve spent a lifetime chasing the hoops and boxes, maybe even feeling a great sense of accomplishment in having done so. The structure is comforting. It gives you a formula, a direction.

The problem, of course, is that if you’re not careful, it can also make you somewhat indistinguishable from all the other candidates out there.

One role I see this happen with the most is in Project Management. There are so many project managers these days with PMP certifications, it can be tough to separate out from the crowd. Another is Engineers with PE certifications. I’ve often seen it in pharmaceutical and medical device sales as well. Pretty soon the market gets flooded with candidates who are well qualified, but on paper, they don’t stand out from one another.

Often, what has happened, and we’ve all been there, is that so much time was spent trying to be the very picture of PMP or PE that once we’ve achieved it, we’ve also lost any sense of individuality.

So at some point, a decision has to be made: How do I play this game while still building my own story? What hoops do I jump through, and what ones do I skip to forge my own path?

Without doubt, it is a delicate balance. But it is choice that can make all the difference.

About Stephen—-

Stephen Van Vreede is not your average IT/technical résumé writer. Some people just write résumés; he cares about the whole job search. Serving as a Job Search Recruiting Agent, he provides career strategy and concierge job search solutions for senior (15+ years) (ITtechExec) and up-and-coming (NoddlePlace) (5-15 years) tech and innovation leaders. Stephen and his team focus on building simplified, targeted, and certain career move campaigns, be it an external search or an internal promotion. He is co-author of UNcommon with career development leader Brian Tracy. Contact Stephen directly at or send him an invite at see whether Stephen and his team are a good fit for you, text “STUCK” to 866-294-1324 to start a dialogue OR click on the calendar below to schedule a free 30-minute résumé assessment:

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