The things no one tells you about working for yourself

Quitting the 9 -5 to jump into the world of self-employment is an aspirational dream for many. Removed from the corporate environment, your days are sure to consist of relaxed deadlines, comfortable work attire and more time for personal projects.  

And so, with the belief that you’ll have all the time in the world to keep up to date with your favourite TV show, you embark on your self employed life. Only to quickly realise that the grass isn’t necessarily greener and just like the office you’ve left behind, working at home comes with its pitfalls.

As I celebrate my first year of working for myself, I take a good humoured look at some of the things I wished I knew before becoming self-employed.

1. The reality doesn’t quite match up with the dream

The Instagram reality of self-employment will tell you that most entrepreneurs start their morning with an exercise class, followed by a latte or lunch with a business bestie before casually answering a few emails.

In reality starting, building, maintaining and growing a business takes A. Lot. Of. Work. But you knew that right?  

There are many hats to be worn and some of them aren’t going to fit quite right: social media, accountancy, business processes, sales and marketing… Just doing what you do isn’t enough to sustain your business, there are all the additional elements to keeping your ship afloat that require your attention.

Dreams of leisurely mornings musing over a smashed avocado on rye get shelved as the reality of hard graft kicks in. Building your business one brick at a time is more painstaking than those rosy Insta filters would have you believe.

2. You’ll work harder, not less

Many people dream of quitting the 9 -5 so they can spend less time sat behind a desk in a windowless office under an electric light.

Do a quick poll of entrepreneurs in their first year of business and they’ll let you into the secret that working for yourself is likely to mean an increase in hours, not the opposite.

As mentioned above, simply clocking out at 5pm isn’t often achievable. After the work is done comes the accounting, the blog post writing, the social media… I’ll often rack up a 12 or 14 hour work day at the laptop.

The positive about the increase in hours is that the effort you put in is rewarded by growth in your business. Not working to feather someone else’s nest, your passion and determination to create something of your own will pay you back in the long run, plus benefit the people you are working hard to serve.


3. You’ll hear “What exactly do you do?” a little too often

We rely on job titles to pigeon hole people into categories. There are no questions needed when someone tells you that they are an estate agent, that’s just what they do.

But when someone asks you what you do, you’ll suddenly realise a one or two word answer isn’t enough to explain what your dreams are and how you’re striving to reach them. Before you know it, you’ll be talking to glazed eyes and the inevitable follow up question after a pause. “So what exactly do you do?”

Nailing down a sentence to answer this question was one of the pivotal moments in my business. Having the confidence to explain what I was all about helped me in both casual conversations and those all important networking scenarios.

4. It will suddenly get really quiet

As soon as you step away from the office environment you’ll lose all the noise. No phones ringing, background chatter, kitchen banter, sneaky lunchtime drinks; even the work Christmas party will fade away leaving you sitting alone in your home workspace.

Yes! I hear you cry, exuberant at the thought of a zen-like environment in which to work, at your own pace and in your stretchiest items of clothing.

Fast forward a few months and you’ll realise that the only person you talk to is the postman as they drop off next door’s parcel because they know you are in during the day.

If you have a pet, they will suddenly be your co-work spirit animal as you vent your frustrations after a long day of silence. Failing that, your desk plant makes a very attentive listener.

Bonus tip: Why every solopreneur needs to find their tribe.

5. Leaving the house becomes a big deal

Working from home has its definite perks; a commute is one thing I don’t miss. If I leave the house in the morning it’s because I’ve chosen to fit in a walk before sitting down at my desk.

However, the downside of working from home is that hours (if not days!) can pass without you leaving your four walls. If much of your work is done remotely for clients, the reason to leave the house is completely eradicated.

Suddenly, you’ll realise you’ve worn the same pair of joggers for an entire week and you’ve not stepped foot out of the house in a very long time.

Scheduling in a meeting, visit to the supermarket or even a walk around the block becomes a vitally important part of your week.

You may like to read: Ways you can fit more exercise into your day when you work from home.

6. Work clothing becomes a thing of the past

You know you’ve spent too long working for yourself when your wardrobe resembles that of a student. With an excessive level of comfortable clothing, you find yourself scraping back your hair and wearing your baggiest t-shirt again because you won’t be seeing anyone that day.

Fine for the first couple of months, the novelty of wearing pyjamas all day will soon lose its shine. Although you may not miss the restrictive material of your formal office clothing, you’ll find yourself vaguely longing for any reason to play ‘dress up’ once again and head out for coffee dates or client meetings decked out in your finery because it feels good to do so.


7. The spotlight needs to be stepped in

Uncomfortable truth alert: if you are working for yourself and running a small business, no one will market it unless you do. This can be a real problem if you’re an introverted person, but it’s a challenge you will have to learn to overcome.

Chances are there are a hundred other small businesses in your local area offering similar services or products as you do. Standing out against the crowd is going to be vital to the success of your business.

It’s not a question of who shouts the loudest, but explaining what makes you better than all the rest. That’s YOU in case you were wondering.

Guest blogs, interviews, podcasts, networking events or a feature in the local paper; the ways you can get your story out there are numerous. Make it part of your business plan to seek out opportunities to showcase what it is that you do and connect with your target audience in the places where they hang out. This may be in a Facebook group or at the school gates; wherever they are, you need to be there.

Check out: Why every small business owner needs a professional photoshoot.

8. Revisions are part of the process

If you’re holding back launching something – such as your website – for the right moment, then chances are you’ll be waiting forever.

As you put yourself and your message out there you’ll quickly realise that your first iteration is just that: a draft. Nothing you produce needs to be set in stone and tweaks can always be made based on feedback from your customers.

You will learn by trial and error and the experience of your first few months will help to shape your business moving forward. My website has undergone several drafts as I refine my offering or add new services and I consider it to be a live document, just as my processes, that can be amended in reaction to new developments. 

9. You’ll definitely want to quit more than once

In fact, you’ll probably question yourself on a weekly, if not daily basis.

One of the strangest side effects of entrepreneurialism has to be the moments of self doubt you’ll face. Even if you’re confident in other areas of your life, when it’s only you running the show you’ll start to doubt your decisions and your ability to even make them.

In those moments when talking to your pot plant just won’t cut it, it’s essential you draw upon a support network of friends (or fellow freelancers and business owners) who you can call up for a chat or a shoulder to cry on.

And finally, although there may be days when it is hard to imagine, remember that for every rough day there will be better ones just around the corner. 

If you’re struggling: How to boost motivation when you work for yourself.

What do you wish you knew before you started working for yourself? I’d love to know whether you found the reality of being self-employed mirrored how you imagined it would be, or whether it was remarkably different. Let me know by sharing your thoughts in the comments below!

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Things I wish I knew before going self employed


  1. Derek

    I’m just starting out – so this is a good Eye Opener from someone who has clearly walked the road ahead. Appreciate your sharing this.

    1. Smash Your To Do List

      Thanks, Derek! Good luck for your future endeavours!

  2. Louise Young

    What a brilliant article! Rings true for me in every way – I am 6 months into freelancing and everything you have said directly reflects how I feel! Thanks for publishing this, it’s a great help and encouragement to know I am not alone!

    1. Smash Your To Do List

      Thank you for your comment, Louise! You are definitely not alone on those tough days – we’ve all had them!

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