Connecting the Contours: 12
1 goal, 2 milestones, 3 tasks to do today.
Let’s clear the air. These are the lies that buried me:
You have to choose.
You can rest or you can get ahead.
You can be wealthy or you can be happy.
You can follow passion or you can follow a paycheck.
If they can do it, why can’t you?
You’re not good enough.
The thought of being stuck inside a cubicle for the rest of my life never sat well with me. So, I’d made a career of helping others live out the best days of their lives; all while doing something I loved, in a place that I’d dreamed about as a kid.
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Welcome back or welcome to the Connecting the Contours newsletter.
At 25, I had a decision to make. I’d followed my passion pretty damn far — from learning to snowboard in the dimly-lit driveway of a Boston suburb to getting paid to stand on one in Jackson, Wyoming's Grand Tetons.
But, after more than a decade of funding that passion, a traumatic brain injury changed what I saw when I looked in the mirror. My outdoor life had a ceiling (we love the irony).
Hard truth: the only way I can get back to the mountains, is by reaching financial freedom.
I needed a new plan: leave, grow, build, come back in 10 years.
And I’m obsessed. Because I figured out how to do it ahead of schedule.
the latest | from the blog.
Sometimes I tell stories about time spent in the mountains and about guiding people in the backcountry. Other times, I share insights I’ve picked up on my journey in tech. This? This, strangely, is the result of both — a realization brought about by pattern recognition.
The piece of the puzzle that has snagged my full attention is the potential for economic devastation like we’ve never ever seen. Worse than the Great Depression. We seem completely unprepared for it, and we’re charging ahead like it doesn’t exist.
Now, before we keep going I need you to know that this is not a doom & gloom post. I’m not here to serve you some hot and ready depression stew. I DO have concerns, but I also see opportunity.
you may also enjoy.
the latest | from my own rotation.
watch.
How to create a strategy for your life on Grow With Intention.
The lost art of accomplishment without burnout with Cal Newport.
How to find your purpose with Robert Greene & Dr. Andrew Huberman
listen.
Ravi Abuvala on Growing a Business with Ali Abdaal.
Scott Galloway talks taxes and building wealth with Steven Bartlett
Living in the present with Andrew Garfield on the Modern Love Podcast.
read.
All Day I Dream About Substack (ADIDAS) by Alex Dobrenko.
$100M Offers: How To Make Offers So Good People Feel Stupid Saying No by Alex Hormozi.
How To Start A Ski Company: The Story Behind Colorado’s Ellis Skis by Max Ritter of Powder.
spotlight.
When You Don't Have A Bachelors Degree, But You're A STAR with Timm Chiusano.
STAR: Skilled Through Alternative Routes.
I love that.
Timm Chiusano is an accidental TikTok star. He’s a former executive, turned advocate for personal & professional growth. He uses his background in advertising and genuine authenticity to share glimpses of his day-to-day life in New York.
This video covers a topic I find important. Here’s someone using their experiences to help others leverage their skills and passions. Employers often overlook skilled candidates despite their relevant experience and abilities… in a time when the workforce is shrinking. Make it make sense — I can’t.
The tides will continue to turn with the rise of AI and online learning resources. We need to rethink traditional hiring processes that prioritize degrees over demonstrated skills.
We need more Timm Chiusanos.
PS — Hey companies: if you turn your internal knowledge base into an external learning resource, you can increase your recruiting pipeline. Just saying.
talk soon.
Thank for being here. See you next time.
onward.
-dm
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