Yoyoyooooo Reader,
I'm writing to you from Tallinn, Estonia and it is my first time here. The weather's rainy and not very encouraging, but the weekend was absolutely incredible.
I just finished running a workshop at the Nomad Summit on transitioning into remote work, and I want to share something important that came up over and over:
Who you surround yourself with determines whether you actually do this.
The Power of Being Around Your People
This weekend, I was in a room with over 30 people who are all asking the same questions you probably are.
How do I transition into remote work?
Can I actually make money this way?
When do I quit my job?
What income path is right for me?
And here's what I noticed: the energy in that room was completely different from being alone with these questions.
When you're surrounded by people who are walking the same path, people who've already done what you're thinking about doing, something shifts!!
You get the knowledge. But more importantly, you get the energy. The proof that it's possible. The real examples, not the Instagram version.
This is non-negotiable for your success.
You could do this alone. But you need people who understand. It simply makes it easier to talk to people. People who have been through what you're about to go through. People who can say: "Yeah, I was scared too. And I did it anyway."
What We Covered (And What You Need to Know)
In my workshop, we went deep on four critical things:
1. Your Why
Not "I want to escape my job." But why. What are you actually moving toward? Freedom? Time? Family? Location independence? Get clear on this first.
2. Your Skillset
Everything you do right now at your job: your skills are worth money. We did a real audit of what you actually know and what you can sell.
3. Income Streams
There's not one "right way." There are multiple paths: freelancing, consulting, remote employment, digital products, coaching. We mapped out which ones fit your situation.
4. Your Exit Plan
Not "I'm quitting soon." But a real plan: when, how, with how much runway, with what income already tested. A strategy, not a hope.
The Biggest Takeaways
#1: What Comes Easy to You Is What Others Lack
This one blew people's minds. You have a skill that feels so natural to you, you don't even think of it as a skill.
But someone else? They're paying for exactly that.
That's your first income stream.
#2: Personal Brand Matters
If you want to make money remotely (whether it's freelancing, consulting, or coaching) people need to know who you are and what you do.
Start building your personal brand now. Before you leave your job. On LinkedIn, in your network, in conversations.
Because when you're ready to launch, you won't be starting from zero. You'll have momentum.
#3: Grow Your Network BEFORE You Leave
This is critical and most people miss it.
Don't quit your job and then try to find clients. That's backwards.
Build relationships while you're employed. Connect with people in your industry. Show up. Be helpful. Be present.
Then when you transition, you already have a network to sell to.
Networking isn't sleazy or fake. It's just showing up and being genuinely interested in other people who are on similar paths.
The Real Difference Between Dreamers and Doers
Here's what I saw this weekend:
The people who were energized and clear weren't the ones with the most money or the best circumstances.
They were the ones who were connected to others doing the same thing.
They asked real questions. They got real answers. They saw that it was possible because they were literally in a room with people who had done it.
And that changed everything.
What This Means for You
If you've been thinking about transitioning to remote work or going nomadic... you shouldn't do it all alone.
You need a community. You need people who understand. You need real examples and real guidance.
That's why I created the Nomad Transition Program. That's why I'm doing these workshops. That's why I'm here building these connections.
Because isolation keeps you stuck. Connection moves you forward.
Your Next Step
If you're ready to get clear on your path... your skills, your income options, your timeline, your exit plan... I want to help you.
I'm offering free 1-on-1 Assessment Calls to map out exactly where you are and what your next move should be.
45 minutes. Just us. Your situation, your numbers, your goals.
I'll tell you honestly what I think you should do next.
This energy we had at the summit, the clarity, the momentum, the connection... that's available to you too.
You just have to take the first step.
What I Want For You This Week
Look around at who you're surrounding yourself with.
Are they people on the same path? People who understand your vision? People who've already done what you're thinking about doing?
If not, find them. Join a community. Go to an event. Book a call.
Because who you're surrounded by determines whether you dream or whether you do.
Sending you so much love (and the reminder that you're not alone in this),
Jess
P.S. What's one skill you have that you've never thought of as something people would pay for? Hit reply and tell me. That's often your first income stream.
