This Career Pivot Playbook features Dennis Hedenskog, an entrepreneur and the writer behind his Substack, where he writes about energy management and modern work.
He started in entrepreneurship and never left.
Over the years, he built companies across sales consulting, coworking, workplace strategy, and real estate development. He questioned standard answers and built alternatives when they did not make sense.
Eventually, he saw that the real asset was not the companies. It was the skill set.
Solving problems with limited time and money. Making decisions without full information. Staying steady under pressure. Creating structure where there is none.
The shift was not a reinvention. It was an expansion.
Entrepreneurship evolved into fractional COO work. Clear priorities. Better systems. Fewer operational fires. At the same time, he began writing about energy management for knowledge workers facing constant cognitive load.
Today, he runs a portfolio career across advisory work, writing, and digital products. His Substack supports that system. It sharpens his thinking. It builds trust. It compounds over time.
In this Playbook, Dennis breaks down the moment he knew it was time to diversify, why audience growth does not equal income, how he chooses platforms, and what nearly made him quit.
He also shares the decision that set his direction early and the filter he now uses before committing to any new path.
✨About Career Pivot Playbooks
A public archive of modern career blueprints…
Most careers no longer follow a straight line.
People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.
Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.
The focus isn’t outcomes.
It’s about how careers are shaped in practice.
About Dennis
Dennis Hedenskog is the writer behind his Substack, The New Habits Newsletter, where he explores energy management, modern work, and operational clarity.
He is an entrepreneur, fractional COO, and former founder across sales consulting, coworking, workplace strategy, and real estate development who built his career by questioning the status quo and creating his own structure.
Today, he blends operational execution, entrepreneurial experience, and energy management to help founders run better businesses and help knowledge workers manage the demands of modern work.
You can follow his work here →
Dennis reflects:
“Can you share a bit about your professional background and the path that led you to where you are today?”
As a professional, my life has been all about entrepreneurship. A mix of rebelliousness and inability to accept solutions that don’t make sense to me has led me to launch businesses across sales consulting, coworking, workplace strategy, and real estate development.
The experiences from entrepreneurship and distaste for the status quo have led me to where I am today: running a Fractional COO business and a content creation business aimed at helping knowledge workers with energy management.
“What sign, moment, or slow realization told you it was time to diversify, and what did you have to push through to actually act on it?”
I’m a curious person with an interest in several things, and I wanted to have a professional life where I could explore different topics and make use of my experience in various fields.
“Which skills or experiences from your previous career unexpectedly became an advantage in what you do now?”
Solving problems with too little time and money. This is basically what entrepreneurs have to do, and this has helped me act with calm and confidence in my business life, and it’s still my edge and source of momentum.
“How did you decide where to build visibility or credibility (Substack or elsewhere), and what role does that platform play in your overall career or income mix?”
Substack is my main platform today, and for one simple reason, it’s the one that makes me feel the best when I use it. My relationship with social media has been complicated over the years, and my guiding principle for choosing a platform is what Tim Ferris says “if my body doesn’t say hell yes, then it’s a hell no”. I go with that, rather than focusing on the ability to earn money.
“Who is your work really for, and what problem do you solve so well that people are willing to pay for it?”
I help entrepreneurs solve everyday challenges with improved structure through my fractional COO business, and I help knowledge workers deal with the demands of modern work by teaching energy management.
“What turned out to be harder than you expected when you started… and what was easier than you imagined?”
Growing an audience has been easier than expected, but I’m learning that vanity metrics (like your following) doesn’t necessarily translate into earnings. So packaging, communicating, and earning the trust of your followers is the biggest challenge.
“How have you found the journey? What advice/strategies and tips would you give to others wanting to grow their audiences?”
I’m surprised over how much I like the people on Substack. I feel that the experience is genuine and more honest than on other platforms. And my advice for others is to be honest about what value their life experiences can give others and learn how to translate that into actual learning for others.
Also, I’d like to encourage people to share their actual experiences and not get lost in the “here’s how you grow and make money on whatever platform” advice (which the internet is saturated with). I believe there’s still room for creating art online.
“What nearly made you quit, and what actually kept you going?”
Brushing up against the trade of how much of your time and value you are investing versus what reciprocal monetary exchange is taking place. The trade is still worth it (even though some days I wonder if that’s actually the case 🙂).
“What advice would you give to someone considering a similar pivot or looking to monetize their skills in a more flexible way?”
Focus on understanding what problem you can solve for your potential customers is number one. Spend more time understanding that than you think. Once you get that, you can start playing with the how (platform, packing, delivery etc). Don’t skip the basics.
“What other platforms, audiences, or income streams are part of your portfolio career… and how do they work together?”
I leverage LinkedIn for my fractional COO business. I use that mostly for networking and building relationships.
“Looking back, what’s one decision that changed everything… and what’s next for you?”
The decision to found my first company was a fork in the road, and for me going back was never an option. Moving forward, I’m looking forward to being of service for my clients, audience, and customers.
Links & Resources
Connect with Dennis…
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I’m Katharine — a future-focused career strategist helping professionals build income options and stay relevant as work evolves.
🙏 I appreciate you being here and supporting this growing archive… and thank you to all the creators who contribute, it’s such a pleasure to learn from them.
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This was great fun. Thanks for inviting me @Learn Grow Monetize 😀
Great story. Slow long term thinking we all need for long term foundational success. 🔥