Building Your Own Path


This is right at my two-year anniversary of a job I wouldn’t have been hired for five years ago. While that might not be a big statement for someone in their 20’s or even 30’s, it gets more rare as you get to your 40’s and beyond. You can make an argument that the best career skill to have is knowing how to evolve your career skills. If that bit of Zen tickles your brain, join along and I’ll show you how I got here.

Where have you been and where are you going?
Where have you been and where are you going?

I’m in the middle of reading Range – Why Generalists Triumph in a Specialized World by David Epstein. You may have heard of Malcolm Gladwell’s #1 bestseller Outliers. That book argues that it takes 10,000 hours – 20 hours a week for 10 years – practicing a skill to become expert in a field. Range is the antithesis of that and the quote on its cover is “I loved Range.” – by Gladwell himself. It’s easy to see why the 10,000 hour rule might make sense. Range proposes that becoming that expert in a narrow field minimizes your ability to make connections outside of your niche. There’s also danger in the Tiger Mom approach of early specialization since your end success and happiness depend on finding the right fit for you. If you haven’t tried something, how are you to know whether you’re good at it or not and whether it’s “right” for you.

Range hits true for me because I’ve written my own perspective on it before. About four and a half years ago, I posted a story on LinkedIn called Best Advice: Find Your Y-Axis. I looked at tradeoffs, understanding what makes you happy and what it takes to meet your aspirations, and the importance of knowing when to reassess where you’re at. I followed it up with Your Career Matrix which is a quick way of categorizing that soul searching and prioritizing it. I find it interesting that I never put an end goal in these. Epstein actually notes that long-term goals you work towards unwaveringly can deprive you of valuable chances to pivot. On the other hand, working in a direction and coming to grips with it give you the change to adjust and refine. This is important in all phases of your life because you’re not the same person from birth to death. When you’re older, you’re likely more risk averse; in your youth, you haven’t gained experience and perspective.

What are your skills and what makes you happy?

Here’s where I tell you my story then I’ll ask for yours. This isn’t meant as a brag book, it’s intended to point out where I made key decisions which followed my interests and enabled me to learn. I didn’t give up on paths which ended, I’ve found ways forward where I’ve wanted to go.

This is my rough path. I wanted to design cars in high school. I got a BS in mechanical engineering then an MS. My first job was designing packaging equipment. After that, I pivoted to providing training for then selling mechanical design software. Half a decade later, I moved to a company that let you stream those designs and collaborate on them. It was both a risk and an opportunity. That startup failed and I moved to an eCommerce company as the .com era kicked off. I didn’t have any experience in it which didn’t matter much, because that company failed soon after also. Positioning that bit of skill I built enabled me to land a job at Siebel Systems at the beginning of the CRM space. These pivots changed my career trajectory far away from designing cars but towards new interests. I learned a great deal about sales, service, marketing, and analytics. At Siebel, I picked up technical skills in modeling data, SQL, HTML, business logic, configuring applications, and more. I worked across industries and absorbed how to approach problems new to me while building soft skills. Loyalty and marketing were my specialty and I got to work on some big hairy problems while closing big hairy deals. Eventually, we were bought by Oracle.

As I was getting deep in marketing automation software, the company went on a buying spree. They bought social analytics, marketing, and engagement firms, added eCommerce, took on more advanced marketing applications, and more. This was my Range moment: I wanted to specialize in everything. Well, not specialize in it all, but build breadth and play in new spaces. Nobody was talking about how all all these pieces worked together. I pestered my management and made strong connections in each newly acquired company. Any time there was a need for groups to work together, I was there. I got a newly created strategy role which gave me the freedom to do what I was wanting. Eventually, the company bought a couple more marketing technology companies and built a new business unit for them. I made connections and jumped there as it formed which was another risk, but paid off in new skills and relationships.

While I was making these later moves, I also built skills in blogging, sent newsletters around the company, mentored a great deal, and shifted my skillset. Where I used to demo software and had to be very hands-on technical, now I had to talk about broader concepts and advise on how to achieve business outcomes. I taught myself how to draw better while working on my whiteboarding skills (remember that first software job was training on mechanical design tools). My creative brain grew a lot while I tested new ideas. I formed concepts around unlocking corporate data assets and what’s now known as the Fourth Industrial Revolution back in 2014. I got in a martini-fueled Twitter conversation with a prominent industry analyst who invited me to write Check Out the Digital Factory: Forging Engagement Through Strategy, Data, and Interaction. These are mainstream now, but were very formative in how I worked.

When I finally decided it was time to leave Oracle and found a role I wanted at Salesforce, I had to pull together interview material in a hurry. It was actually much more fun than pressure-filled. I took a flyer and put together a story of the last couple paragraphs filled with a bunch of business-oriented sketches I’d made over time. What I was unqualified for a few years earlier was exactly what was needed now and the team is built on a similar evolutionary path.

As a final note, I’d like to call out a book titled Orbiting the Giant Hairball. That’s an odd name for a book and it looks stranger yet on the inside (see below). It’s filled with doodles, sketches, drawings, and whimsical… stuff – WAY more esoteric than Range or a bestselling Gladwell book. The author worked at Hallmark and became an expert at using corporate assets and resources to do what he wanted while avoiding getting bogged down in the central morass. I bring it up because I was talking with a VP at a client last week and he described how his innovation team works across a large company going from department to department to build something which never would have existed otherwise. As the excitement danced in his eyes about what they accomplished, I asked him if he’d read Orbiting the Giant Hairball. He had and realized I knew just what he was talking about. It’s the framework in Range applied in a quirkier way. Find an interest, find a way to pursue it with mutual wins, then point yourself in a new direction based on what you’ve learned and what you see is next. If you can find a team devoted to that – Like this VP’s or the one I’m on – then you’ve struck gold.

How about you? How have you gotten here? Have you orbited a giant hairball or are you dying to escape one? Where have you taken a risk you’ve learned from? Have you exerted your will to undertake a new venture? What are your goals and what’s your game?

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