Taking Measured Risks In Your Career (3 Key Words)

Part I: Measured Risks

I must have been somewhere around 12… maybe I was 16. I can’t remember exactly how old I was but I remember the impact this comment made on me.

We (my family) were chilling somewhere and somehow the conversation switched to talking about me. My mom made a comment that I have thought about thousands of times since then:

“Jason takes measured risks.”

I honestly didn’t understand what she was saying but I knew she said it in a complimentary way. So I set out to figure out just what she meant, and why it was something she observed and commented on.

If you asked me then I would have said I was not a risk taker. Risk takers were people who put money in something they’d likely lose at but *could* maybe win 20x from. Risk takers seemed irresponsible but sometimes lucky. At least lucky enough to hit a win big enough to finance a bunch of failures.

Having those thoughts about being a risk taker would have made that comment from my mom somewhat concerning. I certainly was no dare devil. Being put in that category would have made me question how I made decisions.

But it was that one special word: “measured,” that got me. That was the word that made me know it was a compliment. Without knowing what “measured risks” were, I figured that “measured” meant I weighed options, I thought about it, and I went intentionally into risks.

That definitely sounded more like me. And, as I grew, and had more risks placed in front of me, I would frequently ask myself how to make sure I wasn’t irresponsibly taking risks, rather, how I could make sure this was a measured – a wise, strategic, well-thought-out – risk.

Part II: What If You Couldn’t Fail?

When I was a very active road speaker, perhaps getting on the road twice a week, I met a lot of people who had a great impact on me. One of them was Heather in the Bay Area. Heather is a recruiter at a big company. He title and background could have been really intimidating. But then I met her. She was one of the nicest, most welcoming, supportive people I’ve ever met. And, I soon found, she loves giving gifts 🙂

As a speaker I usually walk away with interesting swag. Maybe a corporate notebook or pen, or something like that. Many times I’d give those to my kids since I could only use so many pens or notebooks.

Heather gave me a solid metal paperweight for my desk…. it looks something like this:

measured risks what would you do

I was struck by how cool this was. I knew it was not some $5 gift (looks like you can get it for $45 here). No one had spent that money on me while I was a speaker. Usually they pull something out of the swag closet. What’s more, the message spoke direclty to my soul. I was on a very risky venture. Starting up JibberJobber didn’t seem like a slam dunk. There were all kinds of risks. Heather’s message to me was to keep it up, to keep working, and work as if I would not fail.

It was the message I needed at that time. I had questioned my abilities and capabilities, my judgement and my sanity.

Heather joined the chorus of people I respected who were all saying, “KEEP GOING!”

Part III: Your Career Is Riddled With Risks

I’m currently working on a few risky projects. They can be successful or they can fail wonderfully. I’m not afraid of failing but I will not be happy if the time and energy I’ve put into these projects should have gone to some of my other core projects.

But those are measured risks I’ve chosen to take. Invest time and money in some new areas, areas I’m unfamiliar with, to try something that might not work.

Smarter, wiser people might say, “Jason, FOCUS on what you already have going on! Focus on making those uber-successful!”

But, for various reasons, I’ve taken these new things on.

As I think about these measured risks I’ve accepted I have thought about the measured risks in your career. Many people who read this post are in an active job search. Others are hyper-aware of the complexities of their career management and want to be prepared for inevitable transitions.

I’m reminded of the phrase, “Getting out of bed every morning is a risk!”

We could get into minutia pretty quick if we tried to define what measured risks are. Breathing is a measured risk (you know, air polution, possibility of carbon monoxide poisoning, etc.). I don’t want to get into the minutia but I do want you to realize that you, too, take measured risks.

Applying for a job is a measured risk (wouldn’t it be better to figure out how to network in to the organization instead of blindly applying along with 300 other applicants?). Choosing to network in your job search is a measured risk (wouldn’t it be better to just apply online all day long?). Choosing what you wear to a job interview is a measured risk.


What if you accept a job and find out you are working with a bunch of, as Ron Weasly would call them, nutters?

I want you to focus more on the idea that you are intentional and thoughtful about your decision making. We all have to make decisions that are best for us in our career. Whether it’s about education, certifications, where you work, who you work with, what jobs you have… whatever your decisions are about, be intentional.

Being intentional, strategic, and thoughtful is what makes you a “measured risk” person.

It’s also what most of my messages regarding career management are. Be intentional about your personal branding. Be strategic about your networking. Be thoughtful about your follow up.

Taking Measured Risks is Adulting

I love hearing kids talk about adulting and how hard it is. It is hard. But it is also super rewarding. You got all the freedom in the world to choose your own adventure. You can break away from tradition. You can dance to whatever beat you want.

But it can be so scary.

Focus on the upside and approach adulting with a mindset of strategy, intention, and thoughtfulness.

Join me as a measured risk taker. It’s crazy but it’s fun!