Blog - The Winding Road

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Monetize and Scale Your Knowledge

Photo by Aron Visuals on Unsplash Recently, I was talking with a friend who is a knowledgeable marketer with deep expertise in Google Analytics. He’s able to quickly diagnose issues that would take other people hours, if not days, to figure out. He can do this in a matter of minutes. His knowledge is in demand, and he doesn’t do a bit of self-promotion. He recently helped a friend and former colleague out as a favor. This ended up being something he could have charged $1,500-$2,000 for. Not only that, but he could also have documented some of the more …

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Futureproof Your Career (and Income)

Photo by Drew Beamer on Unsplash Every day we think of three things: the past, the present, and the future. When we think about the past and the future, we should use them both to shape our present. The past is just that, in the past. Don’t dwell on it but use it as a learning opportunity. The future cannot be predicted. Don’t try. However, the future can be influenced. What do I mean by this? Well, the things you do today will no doubt have an impact on the future. We just don’t always know in what ways. One …

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What if it doesn’t work?

It Might Not Work This is for those of you who have an idea buzzing around your head but are too afraid to make leap. Don’t read the following things as if I’m saying them. Read it as if you are saying them to yourself. Start with this: It may not work. Now ask yourself the following questions with your idea in mind: What if it doesn’t work? But, what if it does?  What if it doesn’t work the first time and I figure out why? What if I take what I learned, try again, and it works? What if …

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Your Harshest Critic

Originally published on May 6, 2020 We’re our own harshest critic. That’s a fact. Sometimes the criticism is more stinging than at other times. Sometimes we brush it off, but usually, that’s when the stakes are low.  The higher the stakes, the bigger the critic.  If we’re stretching our capabilities, learning something new, the nasty critic will show up again. Always trying to talk us out of whatever it is we’re doing.  It’s a big reason people don’t learn new things – adults at least.  We’re afraid to look like a failure at something we’ve never done and have zero …

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It’s Not You, It’s Them

Feeling Like an Imposter Recently, I interviewed Brian Smith as part of ongoing research I’m doing for a book I’m writing about Recruitment Marketing. Brian is the Recruitment Marketing Manager at Alterra Mountain in Denver, CO. It’s funny, as a former recruiter I’ve interviewed thousands of people talking about things I have no clue about like software engineering and never really felt imposter syndrome nor was I ever nervous before a call. On the contrary, before each interview I’ve conducted for my book, I’ve felt nervous, self-doubt, and a bit of imposter syndrome creep in. Like Seth Godin says, this …

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Reassurance is Futile

“Reassurance is futile” These words aren’t my own. I’m stealing them from Seth Godin. I was recently on an exclusive Zoom call with Seth and other altMBA alums to talk about his upcoming book The Practice that will be coming out in November. During the call, we would discuss a topic that is covered in his book and then break out into small groups of 4-5 of us to discuss what it means to us and the creative work we’re doing. To kick off our discussion around reassurance, he said, “reassurance is futile.” He also mentioned that reassurance is not …

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Becoming Better

How could I have done that better? Like creativity, learning, and becoming better at something is an incremental process — bit by bit. You learn one thing, and that sparks questions, more curiosity, and you dive a little deeper. You begin to uncover edges you never knew existed. Once you’ve done something, ask yourself, “how could I have done that better?” Even if you only find one little thing, that would make it better, right? Then, what happened if you found one other little thing? And on and on. Incremental changes, over time, add up to significant change and improvement. …

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Imposter Syndrome’s Kryptonite

Imposter Syndrome and Curiosity Recently, I was talking with a friend about imposter syndrome and making career pivots. We explored a lot of different angles and examples of this topic. I’m not big on the term “superpower” to describe our core strengths, but I’m warming up to it. During our conversation, I came to realize that one of my core strengths or “superpowers” is actually not knowing what I’m doing. At least the feeling of not knowing what I’m doing or the feeling of not knowing enough. One thing I know about myself is that I’m extremely curious and love …

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What Do Brand Line Extensions Have to Do with Your Career?

You may be asking, what are line extensions? Well, the next time you go to the grocery store or Walgreens, take a look at the toothpaste aisle. What do you see? The reason I picked toothpaste is that I had to buy some a few weeks ago, and I was left confused and overwhelmed. Crest had three rows, Colgate had two rows, and the bottom row was every other brand. There were more choices of Crest toothpaste than I have teeth in my mouth. I’m not sure how many different kinds of fresh taste combined with whitening most people need, …

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It’s a Side Project, Not a Side Hustle

They’re Projects, Not Hustles Recently I’ve been hearing more buzz and conversations around side gigs or “side hustles.” Personally, I hate the term “side hustle,” and I don’t particularly like “side gig” either. Side projects or just projects would be better. As the economy (and world) changes, the way we work will also change. The way companies hire is myopic and transactional. It’s nearly impossible to pivot your career at any point if you feel it’s not going down the path you’d like. Networking, Not Applying Especially if you don’t know anyone working at one of your target companies – …

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