Conquering Self-Doubt in the Digital World

Self-doubt clawed at my gut hidden under the façade of self-confidence. It was 1984, my first day at General Mills. I’d landed my dream job as Marketing Assistant on Specialty Cakes — a reward for my University of Chicago MBA and magna cum laude degree from Carleton College. Despite my stellar educational pedigree, I was scared to death. Was I really prepared? Was I worthy of this responsibility? There was so much I didn’t know. Hallelujah for Tom Manahan the Assistant Marketing Manager whom I reported to. He took me under his wing and reassured me that he’d teach me the ropes… he had my back. And he did. He was a Saint — almost literally. After a year of his selfless tutelage he donated his possession to the church and became a Jesuit Priest. I’ve lost touch with Tom, but I’m confident he has saved thousands of souls more troubled than mine since then.

Over the years I changed jobs, received promotions, and twice owned my own business. Small “wins” gave way to larger “wins” and perhaps even a few spectacular “wins”. I had no doubt that I added value to whatever organization I joined, and somewhere along the journey the self-doubt disappeared… replaced with confidence in my leadership skills, strategic thinking capabilities, and innate ability to turn any situation into another win. Most recently I was the COO of a mid-sized manufacturing firm that didn’t miss a beat during the economic downturn of 2008 and grew aggressively subsequently.

The self-doubt returns

Once the kids were stashed away at college my wife accepted an opportunity that required a move to California. Suddenly I lived in the shadows of Silicon Valley, the heart and soul of the technology industry. For years I’d been ignoring the obvious… that technology and the digital world had passed me by. I’d made little effort to upgrade my technological knowledge, and I got away with it because I’d lived in a low-tech part of the country. If I’d stayed there I likely would have been okay.

But here? In Silicon Valley? I was a dinosaur.

In 1984, my doubts were more perceived than real, but now I was convinced the inverse was true. My fears were confirmed as I applied to a plethora of opportunities — a few well below my capabilities — with nary a callback or interview. Self-doubt crept back into my life like an ugly case of acne.

Hadn’t I outgrown this?

Hadn’t I moved forward?

And you know what my greatest fear was?… That I’d actually get an interview… and be exposed.

I have so much energy, wisdom, and experience to offer — I’m only 57 years old and in great health, am a strong team player, prolific mentor and manager, but I had that one glaring flaw… I couldn’t talk the language of digital… and during an interview a spotlight would shine on that ugly pimple of mine.

The Natives Rule

To state the obvious, Silicon Valley is swarming with digital “natives” — those who grew up with computers and the internet. I, on the other hand, was a super-reluctant digital “immigrant”, now tossed into the epicenter of the natives. I didn’t possess the knowledge or the language to succeed here. The school of hard knocks just didn’t trump my glaring digital voids.

Then one day I was reading day-old news in my paper newspaper and there it was… an article in the business section about a new school offering a Master’s degree in Internet Business (MIB). Over nine months and sixteen modules — all taught by leaders in the Silicon Valley technology industry — I could be digitally transformed. Digital content, marketing, technology, social networks, metrics & data analytics, mobile & apps — everything I was hiding from. They’d clear out the cobwebs in my noggin and re-program it with the knowledge and language of digital. I was all in!

The Journey

So, there I was on the first day of the program’s boot camp. A smattering of people my age, the vast majority significantly younger, and quite a few the same age as my sons. Self-doubt clawed at my gut hidden under the facade of self-confidence… again. I’d come full circle. And Tom Manahan was nowhere to be found.

Today I’m a few months into the ISDI Masters in Internet Business program and I’m relieved to report back — I’m loving it. I’ll make three overarching observations about my experience so far.

First, I’m discovering that I know a hell of a lot more than I gave myself credit for. Put another way, digital isn’t as scary as I thought.

Second, the program is doing a stellar job of filling my digital knowledge voids. Regardless of background, anyone would benefit from this program, but it’s especially useful for the struggling digital immigrant.

And, third, once you know the language of the natives you can collaborate with them quite effectively… and enjoy doing it! The natives in the class bring their strengths to our team projects and I bring mine. Neither would be as successful without the other. My 30+ years of business knowhow and ability to cut through the rubbish to get to the strategic nugget is serving me well.

Through this blog I’ll chronicle my ISDI journey, muse about how technology is destroying… I mean affecting… I mean enhancing our lives (yes, I believe it’s doing all three), and ideally help pave the path for other immigrants to dive into the scary world of the natives. I hope to inspire Generation Xer’s and Baby Boomers to overcome their fears and become productive participants and leaders in the ever-changing digital world we live in.