Back in 2013, I had the pleasure of meeting and working with Scott Dinsmore, author and founder of Live Your Legend, a (now inactive) blog and community built around Scott’s belief that everyone can find and build a career around work they genuinely care about.
He honestly believed you could make a living out of your passion.
And hey, I am not here to put into question his belief or to “coach you” into pursuing your dreams… I honestly suck at that kind of positive coaching (as one of my favorite TV show characters will say, I am not a pessimist, just a well-informed optimist), but there were many things that Scott taught people that were very on point… and they still are to this day.
And today we are going to talk particularly about his love for blogging.
Why is Blogging Important?
Before we get deeper into Scott’s story, let’s start by making some “X Bros” and LinkedIn Gurus mad: no, blogs are not dead, nor are they dying any time soon. Actually, half of the freaking internet is blogs, like, what do you mean? Yes, people have been declaring blogs dead for at least a decade. And yet, here we are.
Blogs are one of the most cost-effective things you can do to market yourself: they build credibility, give search engines something to work with, and create a library of content that keeps working for you long after you hit publish. A social post disappears in hours. A well-written blog post can drive traffic for years.
But beyond the SEO argument (which, honestly, everyone already knows, and nobody finds exciting), there is something more fundamental going on: a blog forces you to articulate what you actually think. It is surprisingly hard to write clearly about something you only half understand, which means the process of writing regularly tends to sharpen your thinking in ways that nothing else quite does.
And yes, I get it, now with AI in the scene, a lot of people don’t even bother and just ask ChatGPT to write the article, maybe read it once, and then post it… But for those out there (like me) who have enjoyed blogging since back in the day and still enjoy the process, there is a whole lot more to it than just prompting, reading, and copy-pasting: figuring out your actual point of view, developing a voice, and giving people a reason to trust you before they ever consider buying from you.
That last part is the one that tends to get overlooked. Trust is built through consistency and specificity, showing up regularly with ideas that are genuinely useful, not just promotional. A blog is the most natural format for that. A real point of view published consistently in a recognizable voice is increasingly rare and increasingly valuable.
And that is part of what made Scott the person he was: someone with an actual passion about getting people to start writing. So let’s talk about what he actually built around that idea
The Start-A-Blog Challenge
Scott had a recurring initiative called the Start-A-Blog Challenge, and it was exactly what it sounded like: a structured push to get people to stop thinking about starting a blog and actually start one. It usually ran about twice a year and was paired with a free 7-day email course, daily writing prompts, a private community for accountability, and a video tutorial on how to get a blog live in under 10 minutes with zero technical experience. Sometimes there would be a little giveaway or freebie here and there as an incentive for participants, and the possibility of being featured on the Live Your Legend Blog if you were among the Challenge Winners. But he was always very clear that any freebie, prize, or feature was not the point.
The point was the writing.
Scott believed, pretty fiercely, that starting a blog and adopting a daily writing habit was the single most powerful thing a person could do to figure out what they actually cared about and build something around it.
He said it over and over, and he lived it himself. Live Your Legend started as a little blog called Reading for Your Success, which he built in 2007 without knowing a thing about technology. That experiment eventually grew into a global community of over 200,000 people, a TEDx talk that racked up millions of views, and a business that let him work from anywhere in the world.
All of it traced back to the habit of writing regularly and putting his ideas somewhere the world could see them.
I am sure that if he were still around, Live Your Legend would remain a strong community. Sadly, most of that content is now gone, as Scott passed away in 2015; without him, the site was eventually wound down. What remains are fragments: old emails, archived posts, the memories of people who were there.
What does this have to Do With Small Businesses and Marketers Today?
Yes, maybe me writing about Scott 11 years after his passing is just a way of coping with something I never talked about. I still remember opening my inbox that morning and seeing the message about his passing… and the shock, and the sadness, and the impotence knowing I was not even going to be able to attend the funeral… Regardless, everything Scott was preaching to individuals trying to figure out their careers applies almost word-for-word to small businesses and marketing teams today.
The mechanics are different. You are not writing to discover your passion; you presumably already know what your business does, and you love it and believe in it. But the underlying logic is identical: a blog gives your ideas a place to live, grow, and be found. It turns what is swirling around in your head (or your team’s head) into something concrete that other people can actually engage with.
And the barriers Scott was fighting in 2014: “I don’t know how to set up a website,” “I don’t have time,” “I’m not a writer…” are still the same barriers that keep small business owners from publishing anything. The tools are even easier now. The excuses, unfortunately, have kept up.
What has changed is the stakes.
Twenty years ago, a blog was a nice-to-have for most businesses. Today, with search engines rewarding fresh, consistent, authoritative content, a well-maintained blog is still one of the most reliable ways to show up when your potential customers are actually looking for what you offer: social media reach is increasingly pay-to-play, email lists take time to build, but a blog, done right, compounds: every post you publish is another door into your business, open twenty-four hours a day, seven days a week, forever.
And yes, standing out has also gotten harder with AI-generated content flooding every corner of the internet (if I read another “In today’s whatever-niche-you-are-talking-about landscape” line Imma have a mental breakdown), but that actually makes a genuine point of view more valuable, not less. What cuts through is a distinct, consistently published voice that sounds like a real person who knows what they are talking about. Algorithms are getting better at rewarding exactly that, and readers can always tell the difference.
The irony is that the barriers have never been lower. You can have a blog live in under ten minutes. You can write in the same amount of time it takes to scroll through your feed. You can start with one post, one idea, one thing you actually believe that your customers would benefit from hearing.
Scott used to say that if later doesn’t become now, it becomes never. The longer you wait, the closer never becomes. He was talking to people trying to find their calling. But, honestly, it applies just as well to the small business owner who has been meaning to start a blog since 2019, or the marketing team that keeps pushing content to next quarter, or anyone who has something genuinely useful to say and just… hasn’t said it yet.
The internet, your audience, and the algorithm are waiting.
