5 Key Lessons in the Pursuit of Continuous Learning

By Mitchel Roling, CEO & Founder at My Dataist

Upskilling is a buzzword and big topic in the business world today. As leadership coaches at CFW, we work with leaders on cultivating a growth (v fixed) mindset, which is essential for successful upskilling. We asked Mitchel Roling, CEO/Founder at My Dataist, who authored an earlier blog on the importance of data literacy for leaders, to share his thoughts (and life lessons) that he’s found invaluable in his own “upskilling” journey, with take-aways to help inform others’ pursuit of marketable business skills and knowledge.

Upskilling is essential for advancing your career. But it shouldn't be a chore.

My grandfather was a jack-of-all-trades — a farmer, woodworker, horse breeder/trainer, and an all-around hobbyist. His career didn't fit neatly into any one category because he was always learning something new. I remember doing my high school geometry homework at his kitchen table when he peeked over my shoulder and asked, "How are you calculating those angles?" After I showed him, he said, "Follow me." Seeing an opportunity, he brought me into his woodworking shop to look at a partially built horse-drawn snow sleigh.

"It's my first time building one," he admitted, pointing to the steering mechanism's complex angles, which gave him trouble. I brought out my calculator, and together, we measured and cut. Within an hour, we had solved the puzzle, providing him with the necessary pieces for the steering components. In the end, we both learned something new.

Encounters like these were not out of the ordinary. My grandfather often dove into new projects without a definitive plan. Yet, he was always confident that he would find his way through, and invariably did, in his unique fashion. He operated on the belief that nearly any skill could be learned—a conviction that guided his quest for gaining new skills (upskilling) and a mantra I strive to live by.

Nothing to fear but fear itself.

The fear of failure is a powerful deterrent. Unlike my grandfather, who seemed to lack this fear entirely – diving head-first into endless projects with nothing but an idea, not everyone is so fortunate. If you resonate with this, overcoming your fear of failure is crucial.

Failure is an integral part of learning. Whether you fear failure or not, learning how to fail with minimal consequences is essential. Manage risks and ensure your failures don't lead to irreparable outcomes. For instance, many applications offer sandbox environments or free trials. Practice your new skills in this low-risk environment before implementing changes that could affect your customers or revenue.

If a test environment isn't available, start with small, controlled tests, learn from any missteps, refine your approach, and then apply your new skills on a larger scale after proving you know what you are doing in a low-risk way. Managing risks ensures that you can still fail without crippling yourself or your company in the process.

Turn big problems into small ones.

My first role post-graduate school was as a researcher, a position I held for four years before pursuing a change within the organization. Our company had just established a new data task force to make our data actionable—a substantial and vague goal. I decided to join.

We had many internal data sources (sales, marketing finance, etc.), but the newest source was a database filled with detailed data on client interactions with our product — data that went largely unused. After consulting with internal leaders, I identified a critical need within our sales teams: they had access to the data, but it wasn't in a useful format. I decided to address this issue. After significant collaboration with the sales teams, I developed a usage report that helped the team assess client health — vital for determining the likelihood of contract renewals.

It was only a single report that took me a few weeks to build, a small step towards our grand objective, but its impact was substantial. It played a role in nearly every renewal moving forward. It's easy to get overwhelmed by a goal's enormity, so it's crucial to dissect larger goals into smaller, attainable tasks and move toward a big goal using small steps. That project immediately led to a full-time role in data, where I continued to tackle big problems, one project at a time.

Only some paths are worth going down.

It's easy to be swayed by the latest trends dominating the headlines, like the current buzz around AI and its transformative potential. However, blindly following these trends might lead you astray.

Daniel Kahneman, the late behavioral scientist and author of the must-read 'Thinking, Fast and Slow,' said in an interview: "You have to follow what you are inclined to do… but you have to be willing to discard ideas that don't work. And if you find yourself very obstinately sticking to ideas that don't work, you are in the wrong profession" (Source: https://freakonomics.com/podcast/remembering-daniel-kahneman/ Min 42:50). He was giving career advice in general, but it applies to upskilling as well. Yes, learn new skills, but if it's clear you've gone down the wrong path, make sure to know when to move on.

Choosing to specialize in AI might be wise if you're in a technical field. However, if you aren't, it may be better to focus on acquiring higher-value skills that are more challenging to automate with AI rather than trying to tackle AI itself. This approach would play to your current strengths and interests, setting you up for a more secure future without leading you down a path that might not fit your career or skill set.

Don’t plan everything.

While it's essential to upskill strategically for career advancement, you should also learn for the sheer joy of it. You'd be surprised how often these pursuits (aka, hobbies) can come in handy in unforeseen ways. Take, for example, my foray into cooking. I became so obsessed that I started a blog: creating recipes, snapping photos, and crafting stories. Though my blogging stint wasn't successful, the technical skills I gained proved valuable later when I became an independent contractor creating platforms for myself and others.

Had I not ventured into blogging—a venture that failed by all traditional measures—I would have struggled much more with the platforms I developed later. I was willing to cut my losses but still learned something from it.

My grandfather's woodworking skills are still strong. And he's still learning, having developed a voracious appetite for reading anything he can get from the local library. Yes, upskilling is about much more than just expanding one’s skillset: It’s very much about having and maintaining a growth mindset, learning from every experience throughout one's life. 

Interested in expanding your knowledge of data intelligence and how you and your business can better harness the power of your data? Contact Mitchel Roling at My Dataist: mitchelroling@gmail.com.

For further information about developing a growth mindset– and taking on other professional development opportunities, contact Cynnie King at cynnie@cfwcareers.com or Rachel Fagnant-Fassler at rachel@cfwcareers.com.