Nomad Designer Learnings: The anticipation conundrum

Sakky B
4 min readNov 10, 2021

We’re coming up to the second month since the inception of the Nomad Designer. I’m currently in Gurgaon, south of Delhi. There’s a wonderful buzz around town as the Diwali festive period draws to a close, the lights still dangling from rooftops, and the smell of firecrackers piercing the senses in the markets.

I’m here for a few weeks to see a good friend, engage with the design community, and see what this historic city has to offer. I’d planned this leg of my journey a few months back, and naturally with the combination of seeing a friend and exploring a city I’d never been to before made me very excited.

Visual example of me being excited.

This is usually the case when we plan a trip. We create a burst of anticipation until we get to the day we start our journey. Dan Ariely actually talks about this in his book Predictably Irrational, where he writes about how the more you think positively about an activity, the more likely you’re going to bias yourself into having that experience.

The thing is, most people don’t move from city to city, plan experiences every month and constantly create new relationships. But for Digital Nomads, we do do these things, we think ahead and we get excited for new adventures. And this presents an interesting problem that I’m calling the anticipation conundrum:

Let’s start with the anticipation part of this problem 👇🏼

Just like with every city, first-time visitor or returning, there are always things to look forward to for these upcoming chapters. This is in fact a wonderful thing, and it actually hits on one of my favourite quotes and toasts:

Always have 3 things with you.

Something to be proud of, someone to talk to, and something to look forward to.

Source — cannot be named for legal reasons

But I’ve found that if you’re not conscious, it’s incredibly easy to get into a state where you are always looking at the next city. You’re always excited for the next thing that’s coming up, the next adventure, that you lose sight of what’s right in front of you. We need to remind ourselves of how fortunate we are to live these lives, how we’re exploring so many different cultures and constantly exposing ourselves to new things.

If you’re not careful, you might look back in a few months and see these cities as blocks in your timeline, instead of the enriching experiencers they should be.

The conundrum side👇🏼

And the reality is you can’t just spitball it and go completely with the flow, because as I mentioned in my very first article, planning is everything when you’re a Digital Nomad. So we’re presented with this confusing situation where should be looking forwards, and we should be planning ahead.

Society rewards those that plan ahead.

Akshay Takru

So how do we get past this anticipation conundrum? As with many things in life, finding the right balance is key. We need to plan, we need to be excited, but we also need to live in the moment. This brings me to how I’m trying to get past the anticipation conundrum.

Plan & release.

Creating the experience, and then letting it go. I think this is the way Digital Nomads can approach their travel planning. We realise that we want to go to this new destination, we figure out what we need to have a successful trip:

  1. Flights
  2. Accomodation
  3. Place to work
  4. Places to see
  5. People to meet

From here, once we’ve fixed or have an idea of answers to these, we release it from our minds temporarily. We focus on embracing and making the most of the wherever we are right now, and we leave the majority of the anticipation to the time of the next adventure.

I think’s its as simple as that, and it probably hits on a the problem of being present in all aspects of life. You can organise things in advance, and then let them be until the moment they happen.

A closing note

Like I mentioned in the article, we’re very fortunate to live these lifestyles centered around freedom. And while it may not be an incredibly damaging thing, it is something of meaning to those that have decided to make a journey as brave as leaving their homes behind to explore all the world has to offer. So for travellers and nomads everywhere, I want to make sure we create the best experience possible in our journeys, so that when we grow old and grey, we can recall our enriching experiences with great fondness.

These are just a few of my thoughts so far as I start my journey to work remotely. I’ll be sharing more as I go via Medium, and also on social media 📹

For cool photos: https://www.instagram.com/sakkybl/

For cool videos: https://www.tiktok.com/@nomaddesigner

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