My 29 Extremely Personal Tips for Surviving Your First Five Years in Business

I quit my job five years ago, two months after making my first bit of money from my new freelance copywriting business.

Sometimes, even now, I have these moments where I’m like, holy fuck, this is my LIFE.

I don’t have to rely on anyone else to earn enough money to live. I don’t have to be anywhere at a certain time each day. I don’t have to do anything I don’t want to do, really. It’s fucking great.

I’ve learned a lot along the way. About myself, about business, and about life. I don’t come from a business background. My parents had working-class jobs. I had only ever worked in bars or nursing homes or garden centres. I didn’t know anyone who ran their own business, except my bosses.

And yet, here I am.

Five years isn’t a long time to run a business, but I’ve passed the timeframe in which most new businesses fail, right? SO LET’S TALK ABOUT HOW I DID THAT.

Fair warning: I am about to contradict myself a lot.

1. Hey, that might not work for you

I’m starting with this because, well, I’m about to share a whole bunch of shit that’s worked for me – but that won’t necessarily work for you.

The absolute best mindset you can go into this with is that there’s no set way to achieve success. I mean, for starters your idea of success might vary wildly to someone else’s. But more notably, some stuff the self-proclaimed ‘gurus’ and ‘thought leaders’ (just puked in my mouth a little) tell you to do will be absolutely bollocks or just simply won’t work for you.

You can follow as many ‘best practices’ as you like, but the businesses that truly succeed are the ones that break the rules and do things their own way.

I recommend studying the way people you admire work and figuring out what you like about their approach and would like to try for yourself. And then do that. Try stuff you like the look of, don’t try stuff that makes you feel gross.

You’re not aiming to copy someone’s exact business model here – you’re aiming to create your own by amalgamating various elements that make sense to you. It won’t be perfect, but you’ve just got to try stuff to figure out how to do this.

An example from my own experience: it’s incredibly common advice to get dressed and presentable and ready to begin work. But I tend to do all my best work, the stuff that requires deep concentration, early in the morning, swathed in pyjamas and slouchy sweaters, with all the curtains closed. My apartment is my cave and getting dressed is a distraction that makes me focus more on my appearance than my work.

2. Find out how YOUR personality works and frame everything around that

Not everyone works in the same way. Rigid schedules and to-do lists work for some people. It makes them feel in control and on track. But me? Try to tell me to start work at a particular time or to do certain things in a certain order and you’ll find me on my Playstation approximately thirty seconds later.

Telling me to do something (like, literally anything) ignites my spirit of rebellion and I am compelled to do the opposite. This is just who I am and how I work, and knowing this enables me to shape my days in a way that works for me. This largely means focusing on how great I will feel once I’ve done my work.

I learned a lot about myself from The Four Tendencies by Gretchen Rubin. I HIGHLY recommended checking it out if you want to learn how to make yourself do your work when you’d rather be eating peanut butter at your kitchen counter.

3. Telling yourself you’re a certain way doesn’t make it true

I used to tell myself I couldn’t work if I’d had less than 7 hours sleep. And I believed it for a long time. It was like a get-out-of-jail-free card for not having to do anything. But you know what? If I had a hard deadline that day, weirdly, I could still work. Working is harder when I haven’t had enough sleep, but it’s not impossible, especially not if I begin in the morning. (True story: I’m working on 5 hours sleep right now.)

Telling yourself you can’t do something because of how you are is just a way of giving yourself permission not to do it. But of course you can do it. It’s not like it’s physically impossible. What kind of bullshit is that?

I realise this point almost exactly contradicts my previous point. But both are true. I don’t know. They just are, okay? I think it’s this: don’t make excuses, but also play to your strengths? Whatever. Moving on.

4. Get enough bloody sleep, would you? PRIORITISE THAT SHIT

Okay, so I don’t NEED over 7 hours sleep but things are a damn sight easier when I get it. So I do everything I can to ensure I get a good night’s kip. Occasionally I will stay up till 2am playing video games, but I know I’ll still wake up by 7am (thanks for that, brain), so I don’t do it often.

There are a few super simple things I do to help me get better sleep: I don’t sleep with my phone in my bedroom, I don’t use an alarm clock, and I go to bed early. I don’t always do all of these things, but I do them 95% of the time, and that’s the best you can expect of yourself.

5. It’ll feel weird and uncomfortable at first, but you’ll quickly get used to not sleeping with your phone next to you, I PROMISE!!!

I stopped sleeping with my phone in my bedroom a few years ago and it has been without doubt one of the best things I’ve done for my sleep and productivity.

I no longer stare into a bright screen if I wake in the middle of the night, which means my brain doesn’t become alert and start buzzing. It means I go back to sleep quicker. It’s useful in the mornings too. I wake up, lie around for about fifteen minutes, then get up.

A friend asked how I don’t just spend the whole day in bed now that I work for myself. I was bemused. What would I do all day? (Don’t answer that, filthbags.)

6. Turn notifications OFF, you self-sabotaging schlep

What the hell is wrong with you? Do you intentionally self-destruct in all areas of your life or just this one? Turn your damn notifications off on everything, except maybe phone calls and text messages. YOU’RE WELCOME.

7. Ev-er-y-thing is practise

You will never be ready. You will never achieve perfection (which is Not A Real Thing). Crack on and do the best you’re capable of right now. Just think of everything you do as an exercise in getting better at it. And you will.

8. Talent is useless on its own

I’ve met a lot of wannabe business owners over the past few years. A lot of them were talented. Most of them didn’t believe in themselves. If you don’t believe in yourself, or at least pretend to (since believing in yourself is hard when you haven’t proven anything yet), no one else will either. Because how can you believe in someone who doesn’t believe in themselves?

These people get beat down on price. They accept jobs at shitty rates. They never demand more. No, they never command more. Their lack of belief oozes through their words, and others capitalise on it. Because it is obvious.

You also need the drive and guts to do this. Running your own business is hard. It requires a risk-taking attitude. Which basically means you don’t dwell on the possibility of everything going wrong. If you struggle to motivate yourself to do things, whether through fear or sloth, this might not end well for you.

9. Good habits are boring but, like, actually quite handy?

This might sound like a weird thing to hear from a self-proclaimed rebel who hates being told (even by herself) to do something – especially if it’s something she should do every single day.

But that’s not what habits are. When you form a habit, you don’t NEED to tell yourself to do it. You’ve trained yourself to do it automatically, without thinking, so there’s nothing to rebel against. And doing this can enable you to form a sort of natural rhythm to your days, meaning you flow through them with much less effort and much better results.

Better Than Before by Gretchen Rubin and The Power of Habit by Charles Duhigg are two great books on the subject.

10. Focus

You will do better work if you don’t go on social media or check email for the first few hours of the day. This is just a fact. Deep Work by Cal Newport talks about this.

11. An ergonomic desk set-up is CRUCIAL (unless you like pain)

Before I started my business, which involves a heavy dose of sitting at a laptop each day, I was a barmaid. I rarely sat down. I was always doing something, whether it was pulling a pint, carrying food to a table, or changing a barrel in the cellar.

Switching from being on my feet all day to sitting at a desk all day, I noticed a huge difference in my back’s health. Back pain, man. What a bitch. Now though? I rarely get it, because I’ve bought equipment that helps with my posture. I use a stand for my laptop to bring it up to eye-level, and I have a separate keyboard and mouse. I also have a kneeling chair.

Find equipment that works for you. It may take some experimentation, but it will be worth it. SO WORTH IT.

12. Effective networking isn’t the gross thing you think it is

I never go to ‘networking events’, but that doesn’t mean I don’t network. I prefer to think of it as ‘making friends’. Get to know people, grow to like them, and they will do the same back to you. Trust and respect will happen and things will be glorious.

Last week I picked up a fun last-minute day’s work because a friend of mine was ill and couldn’t do it herself. We met on Twitter a year or two ago and have since become actual real-life friends – and she thought of me first when she was looking for someone to help her and her client out.

The week before, I gave a talk at Edinburgh College about how to write good copy, because a bunch of fellow copywriters in Edinburgh put my name forward. But if I’d never got involved with the Edinburgh copywriting scene, they wouldn’t even have known who I was, let alone thought I was the type of person who’d be good at talking to students about copy.

My involvement in the Edinburgh copywriting scene also began online, by the way. The internet is how we meet people now. It’s not weird any more. So get involved. Facebook groups and Twitter are good places to start.

13. Professional and serious are not the same, arrrgghhh goddamnit!

‘But don’t you want to appear professional?’ That’s what someone asked me after I’d told them you should write conversationally in your copy.

And well, yeah, I do. But writing conversationally doesn’t prevent that. Fuck, I even swear in my writing sometimes and that doesn’t stop me being professional either. Being professional is more about doing what you say you’ll do and being responsive when people talk to you than writing stuffy emails and keeping your collar buttoned up at all times.

Professional and serious are not the same. There’s nothing wrong with being serious if that’s how you really are, but don’t mistake it for professionalism. You can be one and not the other.

14. Selling doesn’t mean being sleazy

People think selling is sleazy because that’s the only time they notice it: when it’s obvious someone’s trying to sell them something, by any means. Sleazily.

But people WANT to buy things, and if you present your offer to the right person, in the right way, they will.

15. It’s okay to watch TV, play video games, and do other stuff just for fun

When I first got involved with the online-business scene, there was a lot of shit going around about how to maximise your efficiency. About how to cut everything unnecessary out of your life so you can focus on ‘the things that matter’. While there’s some truth in that, YOU should be the one to decide what that means for you.

I heard over and over again that watching TV or playing video games was a waste of time. We should spend all our time doing something to improve ourselves!! Literally all of it!!!! Read books on your phone while queueing at the supermarket! Study courses while you’re on the stationary bike!! Listen to podcasts while you have sex!!!!

Jesus Fucking Christ. It’s okay to relax sometimes and just do things because you enjoy them, you know? I spent approximately 17 hours playing Dragon Age: Inquisition this weekend, and not only am I not exaggerating, it was fucking great. ENJOY LIFE SOMETIMES OR WHAT IS THE POINT?

16. This doesn’t have to be some grand, sweeping commitment to improving all of humanity

It’s okay if your work doesn’t revolve around changing the fucking world. It’s okay to want to do something just because you’re good at it and enjoy it. There doesn’t need to be a deeper meaning, other than the one you decide for yourself, which can be as simple as ‘I don’t want to have a boss any more’.

17. The digital nomad life suuuucks

I started my business with the goal of being able to work from anywhere. My original intention was to work and travel at the same time, aka become a digital nomad. I tried it and it sucked. You don’t do great work OR great travel. It’s still awesome to be able to work from anywhere, and I do take advantage of this, but now I spend most of my time based in Edinburgh and my work is so much more satisfying for it. And so is my travel, for that matter.

18. ‘Passion’ is a terrible reason to start a business

Trying to start a business based on passion is like trying to be in love with someone on the first date. It’s just not how it works.

I didn’t choose to become a freelance writer because I was particularly passionate about it. I was writing articles about TV antennas and heat exchangers when I started out. It was not a passionate love affair, I assure you.

As far as I can tell, most ‘passion businesses’ happen by accident. Someone does something because they love it – with zero intention of making money from it. Then, because they’re good at it and see a way to monetise it, they do.

If your starting goal is to make money, you have to do things the other way around. Begin with something you can monetise, and you’ll probably grow to love it anyway, because that’s what happens when you devote yourself to something.

Yes, I’m completely in love with Untamed Writing now, for the record.

19. Concentration is fleeting and will abandon you in short order

The first time I drove for five hours without stopping, I was astounded at how tired I felt at the end of my journey. ‘All I’ve been doing is sitting here. Why am I so tired?’ And then I realised that I was concentrating for the entire time. And using your brain can be just as tiring as exerting yourself physically.

It makes sense that this applies to running an online business too. There’s a lot of thinking involved. I max out at about four hours of concentration. That’s why I start work in the mornings. If I start work in the afternoons, after I’ve already been awake for a while and done some other shit, I don’t have as much concentration left.

20. It really is a good idea to ‘niche down’

This is solid advice that I tell other people (but haven’t always listened to myself). Focus your offering. At least make sure all the things you offer are relevant to the same sort of person, and make sure they all come from roughly the same skill set, because you want people to know that this is what you do and you are fucking good at it.

Focusing your offering is also extremely useful for eliminating headfucks. Having one specific group of people you target everything towards makes things SO MUCH EASIER. No more fretting about what your email opt-in gift should be, or who to write your blog posts for, or whether you need to split your website in two.

21. Your writing voice will develop over time

I credit the fact that I’m such a conversational, entertaining writer to the fact that I’ve been doing it since I was 15. I started a LiveJournal and I wrote about random crap, mostly to entertain my friends. Over the years, this habit has continued, evolving over many (many many) blogs and social media platforms. It’s ingrained now. It’s been a part of me for over half my life.

My point is not that you need to write for YEARS to find your voice. My point is that you need to practise, and that your voice won’t be as strong now as it is in five years. The way I write now is different to the way I wrote five years ago. But it wouldn’t be if I hadn’t written anything during that period.

What’s that proverb? The best time to start is yesterday. The second best time is now. Stop lamenting over how long this will take, or the fact that you’ve left it too long, and just begin. Five years ago, when I started this blog, I thought I was too late. Blogging was heavily saturated now. No one would read my stuff. I couldn’t get noticed or make an impact. And yet here we are. Hi. Thanks for reading.

22. Most people’s writing is full of redundant crap

Most people are terrible writers, and I blame school essays. Trying to hit arbitrary word counts and talk in an overly formal tone does NOTHING to help you become a good writer. Sigh. Anyway, cut out the crap and your writing might become something people don’t fall asleep to.

23. People don’t have short attention spans if you write something worth reading

Someone once responded to one of my newsletters (which, if you’re subscribed, you will know are loooooong) asking how effective I found them for my business. ‘The experts say no one reads emails over 250 words any more,’ he said. Or some crap like that.

I just pointed him to my subscribe page, which contains a whole bunch of testimonials from other people who’ve responded to my emails saying how much they love them, the fact that they’re the only ones they look forward to opening or read all the way to the end. People who, yes, go on to buy from me.

Write something worth reading and, holy shit, PEOPLE WILL READ IT. Also, I hate to be the one to point this out to you, but you’re over halfway through a 4000-word article right now.

24. If you want to feel fulfilled, create something

Relaxing is not the way to a contented life. In fact, relaxing sucks if your idea of relaxing is not doing anything. I once took a week off work and I was like I’m not going to do ANYTHING and it’s going to be AMAZING. It was dull as shit and I hated myself the entire time. Find something you care about to work on if you want to live a satisfying life. It’s the absolute best feeling.

25. Blogging makes a huuuuuuuge difference

Not every business needs a blog, but if you’re a freelancer it’s probably a great idea. In Untamed Writing’s early days, I blogged once a week, and later twice a week. And it was one of the most worthwhile things I ever did for my business. Most of my visitors came from Google. They still do, in fact. But they wouldn’t if not for my blog.

Blogging is also ridiculously good for making people fall in love with your brand, trust you, and want to buy your stuff or hire you. It shows dedication and know-how. It’s just, seriously, it’s just such a good thing to do. But take it seriously. Commit to it and don’t throw out any old trash just for the sake of saying something.

26. I reluctantly admit that SEO does matter

I sometimes go off on one about SEO. Like, it’s not the be-all and end-all. But it is important. Like I just said: my business wouldn’t be where it is today without ranking on Google for various useful terms. My freelance writing course ranked number 4 for ‘how to become a freelance writer’ for a long time, and it brought me a lot of traffic, new readers and paying customers (though I don’t offer that course any more).

My problem is the approach some people take to SEO. Ranking on page 1 is fucking pointless if nobody does anything when they get to your site. You need good copy, you need something worthwhile on offer, and a slick design won’t hurt either.

Admittedly I am probably scarred by my earliest freelance writing assignments, which involved churning out useless crap no one would ever read, all for the sake of keywords.

So my thoughts on SEO are basically this: write good shit, write relevant shit, and write it in the words your target audience would actually use. Then people will find your stuff, enjoy your stuff and share your stuff, and Google will notice. It’s a simple but effective recipe.

27. Content marketing is good for selling products, networking is good for finding clients

I doubt many of my copywriting clients read my blog, or at least not on a regular basis, and I’m sure they don’t sign up for my emails. People who are willing and able to pay good money to hire talented copywriters tend to be busy. They have a lot going on, whether that be managing a team or launching a new startup or whatever. They’re not looking for inspiration or information – they’re looking for someone to get the job done. So they ask people they know and trust for recommendations.

On the other hand, people who are at the beginning of their journeys into business are looking for inspiration and information, especially if they’re going it alone. And they often intend to write their copy themselves, whether through necessity or desire. These are people who are more likely to spend money on ebooks and courses. I’ve found content marketing highly effective for reaching these fine people. Provide useful, inspiring information for free, and people are more likely to trust that you can help them.

Caveat: growing an active following online, through your blog and social media, shows potential clients you know what you’re doing. One of my recent clients was astounded when I got a lot of responses to a Twitter poll I conducted to help with his copy, despite the fact he has several times as many followers as me. IT’S NOT HOW BIG IT IS, IT’S WHAT YOU DO WITH IT. Cough.

28. Don’t wait until you’re inspired or in the mood

It’s true that it’s easier to crack on with your work when you’re in the mood to do so. But, like, when the fuck does that ever happen?

You’ve just got to begin, whether you feel like it or not. You’ll find you quickly GET in the mood. I dunno, that’s just how the brain works. Set it down a particular path with a little effort, and it will continue along it with much less exertion.

It’s nicer to start work when you feel like doing it, of course. I have a couple of tricks to help with that: read a related business book (this is dangerous, though, as you might end up reading for five hours) or spend the first few minutes in bed thinking about what you want to accomplish today and where doing so will lead.

But better than trying to get in the mood is to set yourself up for success. Turn off the internet the night before. Have a dedicated work space where the only thing you do is work. Form a little ritual that signals that work is beginning. It’s not easy, but it is worthwhile, like most things on this godforsaken planet.

29. Just fucking go for it

You have to try things if you’re going to get anywhere. So fucking try them, or you will never know.

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