A friendly advice to stop giving advice

On asking questions instead of giving advice.

At my favorite conference-at-sea last year, I joined a workshop on mastermind groups. Besides doing a great job with defining what it is and can do for you, Jimmy and Alex also set a few guiding principles. One was daring to be vulnerable. Another, which I want to highlight here, was to focus on asking questions instead of going into problem-solving mode.

Simple advice, yet, so difficult to follow.

We sat down in groups of four to practice our own mastermind session, with 12 minutes per person to share a challenge and for the others to give input. When you hear someone describe what they struggle with, you listen through your own history filter—you fill in the blanks, based on what you experienced. They say a, you think aha, the whole alphabet. And you’re rarely aware of doing so.

Having short conversations where people did not give unsolicited advice, and instead tried to really understand what you were saying, made it clear how rare that is. Instead of explaining how I already knew this or that, I got the chance to dive deeper into my real issue.

And the same goes how how I act. To listen and ask open questions, it’s hard. Sharing your story, which you know by heart and can adapt like it’s play-dough to fit into anything, is easy.

But you can probably guess what makes for a better experience.

LifeSanna Stefansson
More ways than one

The loudest stories you hear about people living the digital nomad life usually follow a similar narrative; after a few years on the traditional path, they went traveling, got hooked on the freedom, and managed to grow a successful travel blog/build an online marketing business/something about dropshipping.

You could see it as a contemporary hero’s journey, the free spirit who escaped a slow death by cubicle, and who’s triumph can be perfectly captured in an Instagram post.

Entertaining as they are, if you’re involved in this community or dig a little deeper, you know that there’s a full range of other stories to be told. There are plenty of ways to both make money* and structure one’s time.

I would describe myself as somewhat location independent. There are periods when I’m working on assignments, fully remote. Some months I’m immersing myself in experiences or to work on personal projects (that might eventually see the light of day). Other times, like right now, I’m based in Sweden for clients requiring me to be on location.

In other words, it constantly changes.

Sometimes when I talk with friends who might feel a bit stuck in their lives, they say that they, too, could just leave to go traveling, but they can’t because of a, b, and c. In an attempt to diversify the picture I usually start explaining how my life isn’t perfect. But that’s not the point. It might look like I did just what I talked about earlier, quitting my job to go traveling, now freelancing from whatever tropical destination I please, insert sunset picture, THE END.

Not quite the way it happened.

The first part of the story is that it took many little steps. I went on a week-long charter to Greece before I spent a month backpacking in Australia. I worked from Bali for three months while employed before quitting my job. I tried finding a job in another country before I embraced freelancing. There was one step forward, two to the side, one back, and it all adds up to progress. It’s not a straight path. If it was, it wouldn’t be interesting. And I’d rather have interesting than easy.

The other part is that I’m only at the beginning of what I want to accomplish. As I move forward, the more I learn, the better defined my goals and priorities get. Eventually, I want to be off other people’s schedule. Move away from depending on freelance work, build other sources of revenue, that is both sustainable and aligns with my values. Nothing unique about that; nearly everyone I’ve met on this journey has the same aspirations.

There was a time when I would share the process of figuring things out. Writing my way through life, a blog post here, a tweet there. Somewhere along the way, I stopped. Maybe I got tired of internet being my job, or maybe just of my own voice. But this is my attempt to start again. Sharing the experience. Post by post.

Let’s see how it goes.


*My favorite random occupation I heard about from a nomad was the girl I met in Cape Town who supported herself in the unique craft of ghost writing sci-fi monster erotica. Yup. Hero.

Allow me to reintroduce myself*

Hi, I’m Sanna. A somewhat location independent freelancer, helping companies with project management and digital communication, while traveling more than I intend to. Probably too curious for my own good. If you’re new here, I thought I’d give a little backstory.

Three years ago, I quit my corporate job. It wasn’t a dramatic exit, you know, like those who make viral Buzzfeed posts; “ WOMAN QUIT HER JOB—YOU’LL NEVER GUESS HOW”, and there’s a video of a woman base jumping from the 144 floors, with fuck you printed on her back.

No, my situation was different. I liked my job. It was one of the largest communication agencies in Sweden, we had interesting projects, my colleagues were like family. Professionally speaking, that’s where I grew up. I started as a green social media specialist, and over the years found myself passionate about project management and company culture. The thing was, that even though I liked my job, I didn’t like my life, and I didn’t like myself.

Wow, did that sound like a downer.

I felt stuck and I couldn’t find my way out. People are quick to call you brave when you’re doing something out of the ordinary. But that is based on the assumption that you have options. Jumping out of a burning building is brave, but when your alternative is being burnt alive, I don’t know, I’d call it a survival instinct. That was what quitting my job, selling my stuff, and leaving Sweden with a backpack was for me. It was saying bye to a life surrounded by fires, and even if I couldn’t see where they were, I could feel the temperature rising.

Not to be dramatic or anything.

To snap out of the little prison of habits I built for myself, I had to make a big change. Turn life upsidedown, flip perspective. It worked. It wasn’t, and still isn’t, easy. I don’t know what country I’ll be in a month from now, I don’t know what clients I’ll be working with, but safe to say, I’m pretty damn excited to find out.


*Fun fact #1: If I have an opportunity to reference Jay Z, I’ll take it.