It's not Safe to go Alone

Two roads diverged in a wood, and I—

I took the one less travelled by,

There is a common misconception that those who step outside of the box are generally rewarded. Perhaps its because we are shown the few examples of success on a daily basis while no one talks about those who slip through the cracks on that less travelled road.

People like me.

I took the less travelled path; I left school at 16, worked, started freelancing. Then I worked part time in retail, pushed through a college HND, a Bachelors, and a Masters while also working as a freelance in what free time I could snatch. By twenty five I had two University degrees, a college qualification, a mortgage, and a successful freelancing side hustle that kept me comfortable if not wealthy.

Then the trapdoor opened and everything started to crumble.

What to do When the Road Gets Rough

Presumably you're thinking that the choice should be to persevere. Be Sisyphus and push that boulder uphill over and over, confident that you will succeed because this isn't a Grecian tragedy.

The truth is that this could be good advice, but it wasn't for me. I've learned that the key to survival is not simply breaking your back with gritted teeth and bloody nosed hope by your side... it's knowing if, or when, to jump.

Say one thing for me, mama didn't raise a quitter; I pushed and beat at my boulder until my nails broke and my wrists cracked and, eventually, the fucking thing rolled right over me. Then I got up and tried to move it again.

The difference this time is that I knew the signs; this time I jumped before it could flatten me and watched the damn thing fly out of sight. So here I am, standing a quarter of the way up the hill with nothing to my name but fancy, specialist qualifications, a beat up old Dacia, and a bedroom in my grandmothers house to my name.

I'm the kind of person people find interesting at parties. I'm the person that people say - "I wish I had done that!" - to over a table, safe in the comfort of the sensible choices that led them to their comfortable nine to five... and I wouldn't change it for the world. My past, I mean. I very much intend to change my present.

What do you do when the road less travelled gets rough and you're stranded without purpose? You decide whether to go back or push on.

Me? I need a new boulder. In the meantime, I figured I could dish out some of what I learned dragging my boots through this poorly laid track.

Tips for Wanderers at the Start of Their Road

Don't worry, I'm not pretending to be a sage... after all, I'm writing this from my childhood bedroom. This isn't me lecturing you about how to succeed; it's me up to my neck in quicksand shouting at you to avoid the slippery rocks and weak bridges.

You, my intrepid friend are going to succeed where I failed... and I'm going to cheer you on every step of the way. Assuming I don't disappear like Artax in the swamp (I know, I know, neither of us wants to remember that scene).

Let's define the parameters first; my experience won't help you much if you want to climb the corporate ladder or you intend to take the legal world by storm.

I collect vagabonds and ragamuffins; people who are comfortable with the idea of being dirt poor well into their adult life, who can live out of a backpack, and who, most importantly, aren't too proud to start cleaning toilets for a living when the road gets rough.

Here's where we start;

Have a Plan

I jumped in with no plan, and while I won't tell you that's the only reason I sank it probably didn't help. I've always been a go with the flow kind of person; I white knuckle my way through everything.

To be fair, it worked out well for eight years or so.

But I could have done better. Whether you want to work freelance, start your own business, or make a living in a specialized field of work knowing roughly where you're going is helpful.

Prepare for it to go Wrong

Your plan is not concrete; it's more like sharpie on shiny plastic. It'll hold up to a lot... but if anyone finds reasonably strong acetone you could be fucked, for lack of a more elegant word.

Have a plan B, a plan C, and hell, a plan D through H... and an emergency plan if you can.

What are you going to do if everything goes tits up? Move in with your grandma? I mean, shit, it's better than being homeless but I'd recommend something a little more... well, more, if you're overly attached to your self-image as an independent free spirit.

Keep Your Overheads Low

There will be good days. Oh boy there will be good days and you'll start to think you can count on them.

That's a fucking lie - you cannot count on anything but death and taxes.

If you don't need it, you don't need credit for it. Keep your regular financial reponsibilities as low as you possibly can and squirrel away a little extra for the inevitable D-Day onslaught of emergencies, low income, and repairs that will gang up on you.

Diversify your Skills

"Find your niche and stick to it" is great advice for people building a digital nomad existence from the safety of a steady job. They get to join the road when they have all their equipment.

You, my little rogue, are considering starting this path with nothing but the shoes on your feet and a head full of dreams, right?

So, get used to the idea that you will have to work on projects you don't like, probably for people you don't like, maybe at a rate of pay that's just this side of criminally shitty.

If you can write, you can learn to proofread, if you can learn to proofread you can learn to edit, and if you can do all that you can learn basic design skills and start selling social media content packages.

I mean, shit, maybe you won't do it all well, but the people who hire freelance writers to plan an Instagram campaign probably can't afford to work with big marketing companies.

Don't get me wrong; I'm not telling you to scam anyone - don't take a job you know you'll do badly. But if your client needs a service that you're fairly certain you can provide, and you're honest with them about your level of experience it's a good way to bring in extra money.

There are plenty of people out there who don't have these skills in the most basic form, and if you can offer them a helping hand within their budget, most of them can be chill about you being on a learning curve yourself.

Work Strategically

You will need to work traditional roles at times, in fact I recommend it. If I did all this again, I would take temporary, part-time work every christmas season at least. Why?

Well, its guaranteed money; the festive season can either be the busiest or most quiet, depending on your niche. Worst case scenario, you live on what you make in this job. Best case, you're dog tired for three months as you struggle to keep up with your workload... but come February when everyone is in hibernation, waiting out the Christmas overdraft, you have a little extra in your pocket.

Better yet, I would have taken part time hours at a supermarket of some kind. Eight to twelve hours a week isn't a big commitment, and when you work with a company for long enough you can get discounts on their products.

A 10% staff discount on groceries is something special when the road gets rough.

Abandon Your Pride

There's no shame in losing, no shame in being told you were beaten out for a job or prize by someone who has more experience or a better portfolio. Don't listen to that voice in your head.

You are not put on this earth simply to rack up achievements in your professional life.

A full, adventurous life is worth living no matter what your bank balance looks like; you'll need to tell yourself that often when things go wrong. Your pride can heal, but if you refuse to ask for help or give up opportunities to protect it...well, you might find that harder to recover from.

Do it for the Story

You didn't choose to go off trail because you wanted a normal life, and you're not taking the harder path because you want to sit at a dinner table and say,

"Oh, you know, same old same old."

I can give you all the good advice in the world about how to stay out of the quicksand, but you have an adventurous spirit. I can't look you in the eye and tell you that I would change the impulsive, maybe a little dangerous, things I did because I did them for the fun of it. I did them for the stories.

You can do everything right and still fail, and I can tell you from personal experience that ending up in the pit, up to your armpits in debt, looking a whole new path in the face doesn't completely suck when you can sit at a table in a warm, dimly lit pub and draw real belly laughs out of the people you love with a few, well-worn stories.