Had an interesting conversation recently via LinkedIn with a former Director I had interviewed with for a manager position in my mid 30’s (Spoiler Alert: I didn’t get the job).

Let me start by saying, I’m beyond happy with where my life is right now, both professionally and personally.

It got me thinking of what I might tell my mid-30 self now, if I had the chance back then…


I’ve never lacked self-confidence (thanks Dad) but NOT getting that job left me pretty P.O.’d at the time. I’m sure I wasted considerable time wanting to prove how wrong that guy was in NOT giving me that job.

The reality is HE WAS RIGHT! Why? … Because HE was the one doing the hiring, and obviously there was something he didn’t see in me, or he saw someone better suited for the position at that exact moment in time.

35 YEAR OLD SELF: Get over it faster and move on, because I’ve read ahead and everything goes ok – (luckily not sure how it ends yet, but hoping it’s good).


The conversation with this former Director 10+ years later was enlightening. I was interested in how he was doing and so I messaged him. I wanted him to know that I had, in some ways, succeeded in managing people after all (not always, but I think most of my employees would say I’m fair but firm and they grow when part of my team).

What I learned was that one of the factors in the decision (not the only one) was that the company considered me a rainmaker, meaning I helped generate a significant amount of revenue for them. Partly because of that, they felt keeping me in my current spot of managing accounts was possibly the best way to use my talent at the time.

35 YEAR OLD SELF: “RAINMAKING” is a highly, highly valued skill set; cherish it, make it rain, and count your blessings that saving for a rainy day is what gives you the chance to leave a high-paying position to enter the world of entrepreneurship.


At the time I left to start my first company at 40, I did so because I felt the media world was in for a pretty rapid transformation. In hindsight, I don’t think I had any idea how disruptive the invention of the iPhone would be to how consumers interact with brands. By the time I started our second company, I realized I might be drinking from a fire hose for the next few years trying to learn all there is to know about how the customer journey REALLY works. Immersing myself has helped me to better understand what steps brands can take to positively impact that journey.

I’ve learned a heck of a lot in the last 3 years (not ashamed to admit I was reduced to flashcards in the car to try to better understand some of these crazy acronyms in the data and digital science space). I’m now at a point where the learning continues but we often find we are 6-12 months ahead in our processes than many of our contemporaries – In some ways the student has become the teacher.

35 YEAR OLD SELF: Don’t fool yourself into thinking your industry is immune to change. Take little moments to read, and don’t be afraid or embarrassed to ask or to connect to people who might share a bit of what they’ve learned along their journey. MOST will be more than happy to help you on your path.

PS: 35 YEAR OLD SELF (and anyone else who’s read this far regardless of your age)

ONE final bit of advice: takes risks, succeed, fail, make the wrong decision then make the right ones but…. MOST OF ALL…Have FUN and surround yourself with people who make YOU Better!