Measuring progress in an unconventional life

digital nomads wearing hoodies
“Unconventional friends” – apart from when it comes to clothing, it seems

My “smile lines” are doing my nut, I can see sag lines on my tummy, and I’m beginning to think that four earrings in one earlobe is a bit too ridiculous for someone my age. Oh, and my knees look “different”. Plus I’m sure my hands weren’t this veiny a few years ago.

I’m nowhere near old, but never before have I felt so much older. I’m turning 30 this year – and THAT number combined with THOSE wrinkles is getting me a bit worried…

What exactly should I have achieved by this age?

When my mum turned 30, I was six years old and my brother was four; my parents had a five-bedroom house in the suburbs, a dog, and a BMW as well as some sort of kid-friendly hatchback.

And unless Rob’s been on a secret birthday spending spree for fancy cars, houses and children (bear in mind he got me goulash for my 29th, so it’s unlikely), I won’t have any of those things. I don’t want them either.

But should I want them?

Rob and I live remarkably unconventional lives compared to all the people we grew up with. They know what they should be doing by my age – marriage, babies, houses, cars – and it’s easy for them to figure out if they’re at the stage they’d hoped to be by now.

By comparison, all our digital nomad friends are doing remarkably different things – even though many of us are the sameish age. Some are coupled up but will never marry, and others got married super-young. Some have kids, some have dogs, some have both, many have neither. A few own properties in their home countries, others don’t have any place to call their own, and quite a few invest in property – as we do. Some run super-successful, huge-revenue businesses, others are freelance and have peaks and troughs in income. Some have personal chefs, others only eat raw (or paleo, or vegan, or gluten-free), and many are obsessed with sussing out the cheapest food options in any destination.

Some celebrate “milestone” birthdays with big events or trips, while others, erm, buy their husband a Thai donut from the local market and dress it up with those annoying candles that won’t blow out. (He seemed not to mind.)

There’s just no norm, and there are no expectations. And I have no context for judging my progress in life, because the people who live similarly unconventional lives choose not to conform to other societal expectations. Social barometers don’t exist – which is a weird feeling after 29 years of nothing but social barometers: I can no longer gauge whether I’m “doing well” or making good progress by comparing myself to predefined standards.

Despite all the internal confusion, it’s an amazing and very freeing feeling to be in this position. Sure, my family and friends back home will continue to ask me when we’re going to “settle down in one place” or “at least think about kids”, but it’s easy to disregard such questions because I know how different my life is from theirs. And I have friends who love their freedom as much as I do, and who serve as a constant source of inspiration and reassurance whenever I worry we should be doing more “normal” things.

The tough bit is making sure I’m progressing according to my own standards and expectations. And that really is tough.


It comes down to confidence and headstrongness (for which a better, non-made-up word may exist). Doing away with benchmarks set by peers is scary, but then think about it: why on earth should anyone feel the need to do this or that, just because it’s what all their friends are doing? If you hate five-star hotels, you LOVE own-brand baked beans, and all you want to do is potter around the allotment all weekend (for instance), why are you working like a lunatic 100 hours a week in a job you can’t bear – just because your friends are?

Admittedly, physical limitations will always play a part in how you decide to live your life.

A biological clock isn’t going to take a sabbatical just because you’ve decided you don’t want babies “right now” – and you’re not going to develop invincible shoulder muscles that will enable you to carry a 10kg backpack well into your 90s.

But there’s an awful lot of wriggle room among all those physical limitations, and that’s where we all need to figure out what we want to do, what we want to achieve and where we want to be in the future. It’s about taking a long hard look at what will make us happy and fulfilled – rather than looking to others to figure it out.

Benchmark against yourself

I don’t have an equivalent to the feeling of “Shiiit! My friend has just skipped over to a new job and is making an extra £20k; maybe I should bust out the CV and do a course in social media to improve my chances of getting an amazing new job too.” And I’ve never thought to myself “Oh blimey, they’re all getting knocked up and all their kids will go to playgroup together and marry each other in 20 years’ time… must get a bun in my oven pronto.”

As a result, there’s a risk that I’ll tread water for years because I’m not looking sideways at how others are progressing.

To deal with this risk, I need to define my own standards and expectations and be clear about what I want to achieve (the skills I want to master, the places I want to live, the lifestyle I want to have, the things I want to experience, the stage I want my business to be at, etc.). I also need to decide how I’m going to go about it. Then I need to benchmark against myself – that is, revisit my goals frequently and check that I’m making progress.

What do you think?

Ever so slowly, I’m figuring all this stuff out and realising what a fortunate position I’m in. It’s sometimes weird and scary, but for the most part it feels pretty darn liberating.

If you’re in a similar position, I’d love to know what you think. How do you define your own standards and expectations for yourself? What do your friends and family think? And have you struggled with it in the past, or found it pretty easy to aim for a life that’s outside the norm of how you grew up?

Please let me know in the comments!