Welcome to Connecting the Contours with Derek MacDonald.

this newsletter helps you get clear on your goals, prioritize all that's on your plate, and create work weeks that don't suck.

Hey hi hello.

Creating work weeks that don’t suck get you to good months and great years.

We can prioritize all that's on your plate and help you get there. What does that mean? Sharing ways to create days and weeks where you actually cross things off of your to-do list.

Imagine seeing real progress toward your goals. I’ll show you that it’s possible — without hustle culture or trending fads. Really.

Here’s a quick overview of all you need to know about me and the Connecting the Contours newsletter.

mission.

I'm on a mission to build a world where leadership is a source of clarity and confidence, not stress and overwhelm. I help leaders and teams drive impact through strategic enablement, actionable frameworks, and personalized coaching.

By equipping leaders with the resources they need to succeed, we help create high-performing teams and resilient organizations that drive meaningful change.

We build clarity, alignment, and growth—without the overwhelm.

If you spend enough time reading CtC, you’ll start to:

• define clear goals that bring you closer to where you want to go.

• build systems of accountability that scale with you as you grow.

• prioritize where and how you spend your time.

• strengthen your ability to make decisions under stress.

Sign up to start learning strategies for creating less miserable work weeks.

about me.

at a glance.

I’m Derek MacDonald, a Leadership Enablement Consultant and Founder of DMDC Systems.

At DMDC Systems, I blend consulting, coaching, and education to meet leaders where they are and guide them to where they want to be. From aligning cross-functional teams to building productivity systems that last, I focus on solutions that balance big-picture strategy with actionable steps to get there.

my story.

Wilderness emergency medicine taught me more about pressurized decision-making than any other aspect of my career. My journey with sobriety taught me more about ownership and prioritization than any job I’ve had.

My story includes winding roads through mental health — stretches of despair, of victory, of loss, and of gratitude. Other patches had no roads at all.

My ability to be effective comes from experiences you won’t see on my resume.

At 19 I studied risk management and effective decision-making in a 3 month, immersive leadership development program. I also started consuming as much information as I could from thought leaders like Michael Gervais, Tim Ferriss, Brené Brown, Simon Sinek, Rich Roll, Adam Grant.

It became an obsession.

I've extensively studied high performing athletes, business founders, and psychologists.

My ability to rapidly scale a startup showed me that what I was learning really worked. In my 20’s I guided backcountry expeditions in the Rocky Mountain West, coached big mountain snowboarders qualifying for the Freeride World Tour, and ran the Boston Marathon after recovering from a traumatic brain injury.

• I rode the waves of depression.

• I navigated financial insecurity.

• I climbed out of many pits — some I’d dug for myself, others not so much. I climbed out anyway.

I also worked on the crew of a sailboat in the Caribbean, toured New England as a keynote speaker, and weaved through the service industry in a way that I like to think would make Anthony Bourdain proud. Or, at least, make him scoff a bit.

Life outside of the office has shaped my skill set as much as my professional experiences have.

At work, I build better systems for activating strategies and teams. But, like you, l'm more than my job.

Admittedly, I spend a lot of my time nerding out on sustainable systems and approaches to development. When not training for a marathon or enjoying a sunrise with my snowboard, you can likely find me frequenting local coffee shops and live music venues.

A Massachusetts native, I grew up sliding on snow in Vermont’s Mad River Valley before moving to Jackson, WY in search of big mountains and unconventional approaches to a life well lived. In 2021, I answered the Green Mountain's call and returned to Vermont, where I currently reside.

Outside of work, I have volunteered with Massachusetts HOBY since 2010, developing staffing teams and implementing curricula that inspire young people to become catalysts for positive change in their home, school, workplace, and community.

I've also spent time volunteering for local advocacy programs and coaching freeride snowboard athletes. As a member of the board of directors for Carving The Future, I advised on marketing strategies that empowered underserved youth in Wyoming by providing gear, programs, lessons, and athletic scholarships.

My contributions to Jackson Hole Snowboarder Magazine and NOLS' The Leader seek to elevate communities and voices who've got this life thing figured out.

So, what’s in it for you?

When you sign up for my newsletter, you’ll get posts straight to your inbox.

Topics will range from digital marketing and business strategy to personal anecdotes, mishaps in the mountains, and lessons in leadership I’ve learned along the way.

This newsletter includes:

• new posts from me.

• videos I find interesting from others.

• podcast recommendations that dive into topics covered here.

• helpful resources to read from industry experts.