Lessons From Four Years of Anchor Change
Transforming Uncertainty into Opportunity
This weekend, two stories caught my eye—one about Gen Z‘s career apocalypse and another about Gen X’s career meltdown. I’m sure there’s a Millennial one somewhere. Everyone’s concept of a career is being upended, and it will only continue. I firmly believe that the way we create our professional careers is already changing and will look very different in a few years. This is very much on top of mind as I celebrate my fourth anniversary of starting Anchor Change and am in the middle of figuring out what this next chapter looks like.
What started as a let’s-see-what-happens experiment has turned into something I couldn’t have fully predicted—a portfolio career full of flexibility, creativity, and purpose. But also one that I have no clear vision of what it will continue to evolve into.
FOLLOWING INTUITION
In early 2020, I mapped out what I wanted to work on next and where I might do that work. In an earlier newsletter, I wrote about that process of navigating life after Facebook.
I considered full-time positions and independent work, but January 6th and a job interview later that month gave me unexpected clarity. My gut was loud and clear: Nothing existed that fit what I wanted. I needed the freedom and flexibility of working for myself and to build what I envisioned.
That interview was the final push toward launching Anchor Change. The path wasn’t clear, but the direction was. Looking back, trusting my intuition was one of my most transformative choices.
Since then, I’ve experimented with pseudo-full-time arrangements three times. Each time, within a few months, I knew they weren’t the right fit. That ongoing clarity has made my intuition a professional superpower, guiding my business and well-being.
EMBRACING UNCERTAINTY
The most persistent challenge over the past four years? My relationship with uncertainty.
When you work for yourself, you’re responsible for everything—coming up with ideas, pitching to clients, and keeping track of money. I’ve always worked in fast-changing industries, but entrepreneurship takes that uncertainty to a new level.
Learning to trust that things will work out—surrendering to uncertainty rather than fighting it—has been my most valuable growth edge.
My stress levels transformed when I stopped seeing uncertainty as the enemy and started treating it like a creative canvas.
PANIC RESPONSIBLY: A PHILOSOPHY IN ACTION
That mindset shift paved the way for one of the most unexpectedly resonant ideas I’ve ever had.
In 2023, as AI started dominating conversations, I noticed a wave of fear that wasn’t helping anyone. That observation sparked Panic Responsibly—an approach that acknowledges legitimate concerns while rejecting blind alarmism.
It’s become more than a catchphrase. It’s how I help clients navigate complex, high-stakes problems with vigilance and optimism.
The world has changed dramatically since 2021. We’ve seen political transitions, growing polarization, and the rise of AI, each of which has reshaped how I frame challenges and solutions with clients.
CONNECTION OVER SALES
Of course, running a business isn’t just about mindset—it’s about people.
Nothing brings me more joy than the moment a client realizes I truly understand what they’re dealing with—the impossible tradeoffs, the internal politics, the burnout, and the pressure from every direction.
That feeling of “you’re not alone” is the foundation of my most substantial client relationships.
I’ve intentionally avoided traditional, “salesy” approaches. This Substack newsletter (and then posting on social media) has been my most effective business development tool—letting me offer value while staying present in people’s minds.
More than any formula, I’ve found that treating people like humans and finding a balance between paid work and helping friends has been the most powerful strategy.
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TOOLS FOR TRANSFORMATION
AI has completely changed how I operate efficiently as a solo entrepreneur.
These tools have been absolute game-changers, from creating podcast assets to helping with writing, brainstorming, and scheduling.
I’ve also learned a lot about pricing. One of my favorite lessons was when a company wanted to sponsor my newsletter. I planned to ask for $5,000, but a friend pushed me to ask for $15,000 instead. I was nervous, but they immediately said yes.
Pricing still feels like an art, not a science. But I’ve learned to ask for more and when not to. Clients will tell you if they can’t afford it.
BUILDING A DIFFERENT MODEL
When I started Anchor Change, the only consulting models I knew were traditional firms—offices, employees, growth via headcount. But I’ve learned that’s not what I want.
Instead, I’m building a portfolio life—a business that centers around what brings me joy: writing, photography, podcasting, consulting, speaking, merchandise, coaching, and whatever else I decide to try.
To make it sustainable, I’ve outsourced what I can: a personal admin for errands and travel, an accountant for bookkeeping, coaches for Substack, writing and podcasting, branding help, and project-based contractors when needed.
Whenever possible, I work with other solopreneurs, especially women. I’ve also invested in myself: my book, my website, my branding, and my professional presence.
LOOKING FORWARD
If there’s one thing I’ve learned, it’s this: the future rarely unfolds how we imagine.
The next few years will bring significant changes in AI, geopolitics, and how we work. I’m excited to help people navigate the chaos with truth, steadiness, and curiosity.
I want to propose new ways of thinking about AI, trust and safety, and the intersection of democracy and technology.
My vision board includes publishing my book and exploring creative new avenues for impact, but I’m also holding space for things I can’t yet see.
LESSONS TO SHARE
If you’re thinking about starting something of your own—or rethinking your path—here’s what I’ve learned (and am still very much learning how to master):
Start before you feel “ready.” Perfect alignment is a myth.
Experiment early and often. Try lots of revenue streams and see what sticks.
Find the way that works for you to put your knowledge and expertise out there so people know you exist.
Trust your intuition. It’s wiser than you think.
Price higher than your comfort zone. You can always come down.
Give generously, but know your boundaries. Invest in your karma bank—help others without expecting immediate returns—but don’t let generosity become burnout.
I hope this is your nudge if you’ve been daydreaming about making a change—even if it still feels vague. You don’t have to figure it all out. You just have to take the next honest step. (Something that is way easier said than done, but you’ll be so happy when you do.)
Four years in, I’m more confident that this unconventional, winding path is exactly where I’m meant to be. Is it hard? 100 percent. But so worth it. Thank you to so many of you who have supported me.
What about you?
What’s your relationship with entrepreneurship or career transitions?
Hit reply or leave a comment—I’d love to hear your story.
PS: If you want more people’s experiences of working for themselves, I just got introduced this morning to Substack
, which has a great piece about her life as a freelance journalist.
As someone who has lived the entrepreneurial life for 30 years I found myself notting my head as I was reading your story. Good for you! It is the uncertainty and change that creates opportunities. My biggest opportunity came with the introduction of the Internet. Building a company around E-commerce and web access to records. Scary times but awesome opportunities! Had I known how difficult and painful this all would be, I would not have started it, but !! today I would not miss it for the world. Nothing make me feel as alive as knowing I did this and it is working! Keep going!!