Challenges of self-employment (and how to deal with them!)

I’m a realist.

I knew that leaving behind a 16 year corporate career to become self-employed would bring it’s challenges, and I was OK with that.

But what surprised me was some of the challenges that I just did NOT expect!




I knew I’d have to work on fitting everything in – I have kids and commitments, I say yes to everything and always seem to cram my diary until it’s fit to burst.

I also knew that accounting wouldn’t be a strong point. I have always hated maths, tax returns make me want to cry and don’t even ask me to ring the HMRC, that hold music alone makes me want to rock in a dark corner.



Procrastination is a favourite pastime of mine, and I knew that being self-employed would definitely be a prime opportunity to get sucked into the social media vortex, have me cleaning the bathroom to avoid the aforementioned accounting, or even occasionally fitting in a cheeky episode of Homeland before the kids get home from school.

Of course, these things absolutely have been challenges, and I STILL have to work on them constantly. But some of the unexpected challenges took me by surprise and some of them even took me a while to realise were there…





You can’t do it all

OMG, this has been SO painful for me to admit, but it turns out if you’re self employed you can’t do it all. I eat, sleep and breathe my business. I’m constantly thinking about it. I’m obsessed. I’m always thinking of new ideas, things to do or improvements I want to make. I’m constantly questioning what I’m doing, whether it’s working, can I do it better.

My to do list only ever gets longer, and it would appear I can’t tick everything off. WT actual F?!!

So I’ve had to learn to prioritise and make my peace with the fact that some things will probably never *gasp* get *gasp* done. *Hyperventilating now*.

I want to be all cool and positive about this fact but I’m not in that place yet, so you won’t find any tips from me about how to deal with this, but when I find serenity I’ll let you know!


I’m not as organised as I thought I was

This one was a total shocker. I love making lists, computer management systems, filing. I am the Queen of Organisation. Or so I thought. Apparently, not so much.

It turns out that while yes, I do like to make lists, I seemingly don’t like to actually refer back to them, making them essentially pointless.

Yes I do love filing. But I don’t really do it properly, so I end up with bits of paper all over the place and no idea where anything is.

Ohhhh I love me a good computer system. But there’s this thing you have to do…what is it again…oh yeah. USE THEM.

I don’t know whether to laugh or cry at myself. I’m actually a little ashamed because I am SO good at organising other people but turns out when it comes to my own stuff, I need to do a bit of work.



I am a busy fool (!)

Yes. I have been called a busy fool. More than once.

Ruuuuude!!!  But, also maybe a bit true.

I think it links to all the stuff above – being overwhelmed at the ever-growing to do list and lack of resource to achieve everything. In my anxiety to fit as much as humanly possible into any given day I find myself flitting from task to task in a bid to feel like I’m covering loads of ground, when in reality it’s the complete opposite.

My wise brother-in-law has a saying: “work smarter not harder” – I think he may be onto something.





Self awareness

I think that one of the most important parts of being a solopreneur is the ability to take a step back and self-analyse. It’s so important to be your own harshest critic. Are you focussing on the right things? Are you clear on what you want to achieve? What are your challenges in moving your business forward? How are you standing in your own way?

It’s way too easy to get stuck in a rut with your business. To end up mindlessly doing what you’ve always done even though it’s not necessarily productive or achieving anything.

In my defence, I think this is one area I’m reasonably good at. I do commit to ongoing professional development, and I make time to assess where I’m at and what I can do better.


Clear goals

For me, this has been a hugely important part of overcoming my challenges.  Being crystal clear and completely focussed on my goals has helped hugely.  And this is an ongoing thing because the goalposts move as your business develops.

My goals for my business when I did my proper launch in January 2016 were so different to now.  What I’ve achieved is in no small part to not just setting clear goals, but constantly revisiting them and refocussing what I’m doing to make sure that what I’m doing is contributing to achieving that goal.



Time-managing working hours

I actually feel like a complete nerd and control freak admitting to this, but share it I will because it’s probably the single most beneficial thing I’ve done to increase my productivity.

Every day when I sit down to work, I take a fresh sheet of A4 paper.

At the top of the page, I list the things I absolutely must achieve that day, and schedule them out, estimating how much time I think each task will take.

So it might look like this:


9.30 – 10     Read and reply to emails / social media private messages
10 – 12         Schedule two blog posts
12 – 12.30  Lunch
12.30 – 1     Social media (check, respond, share, engage and pre-schedule)


I know that I can work up until 3pm, so that gives me a couple of hours to play with. I decide how I want to use those two hours and schedule that time out accordingly too.  Sometimes I use spare time for low priority admin, filing or accounting, I might use it for studying my business course, or for researching new ideas.

I am flexible with my approach- if emails take me a bit longer that’s fine, the priority is to get the all important tasks done. Sometimes they overrun, sometimes they take less time than expected.

Scheduling my time out like this stops me getting distracted. I switch off all social media until that block of time comes up, and I just crack on with the ‘must do’ stuff so it’s off the list.

I know it sounds completely OTT but it really works so well for a procrastinator like me!



Be kind to yourself

We are all working our little cotton socks off.

Running your own business is all consuming. You don’t just pitch up somewhere 9-5 every weekday, do your job then leave it behind when you get home. You don’t have the security of a set monthly pay packet. You may have families, pets, a home, elderly relatives to care for, an exercise regime… the list goes on.

While trying to market your business, bring in clients, provide the product or service AND do all of the extra roles from accounting to admin, it’s hard-going before you’ve even thrown in the personal stuff.

So yes – read this post, let it sink in, take something from it. But don’t let it overwhelm or dishearten you, because really we’re all just wingin’ it. Me included.  But some progress and momentum is better than standing still.


Go achieve your dreams, you superstar!


Leave a Reply

Your email address will not be published. Required fields are marked *