You probably shouldn’t quit your day job…


What? Here I am, self professed “quit your day job, do what you love!” advocate, telling your not to quit your day job? Well, yeah.

The thing is, it’s not easy to quit your day job.

It’s really not easy.

And most of the time it’s not sensible, either. Quitting my day job with very few freelance clients, a mortgage, grown-up bills, and an already steady income was probably the most cavalier thing I’ve ever done (but your early-mid 20s are totally made for stuff like that). I was lucky, everything worked out.

But.. everyone’s on a different path & has a different set of circumstances, I’ve seen a lot of people touting the ‘quit your day job! live your dream! make loads of money!’ lifestyle and guys, it’s not always possible. You need to get to a sweet spot that’ll let you ditch your steady income. If I was going to do it again this is what I’d do…

Get your ducks in a row

If you’re dead set on quitting your day job then you really need to get your shit together. I mean really. 

  • Savings, you need them. Aim for around 6 months living expenses to start with (I had 3 months, I wish I’d had more). Think about your incidentals, your dependants, and any emergency funds you might need.
  • Clients, line ’em up. Start being serious about this freelance/new business game well before you actually hand in your notice. Start making connections, putting out feelers, and getting some work lined up.
  • A website, collateral, business cards, it all needs to be ready before you quit. On the first day of your new ‘working for yourself’ position you need to be working on some actual cash making stuff, not faffing around with how your business looks.
  • Support, start telling your friends and family about your plans. Most of them will say something about you having to get a job within three months, take it onboard and prove them wrong. I did.
  • Basic kit, got your laptop? camera? Get them before you quit (and remember they’re a business expense for your new venture, so keep all the invoices).
  • Tax shiz, it’s a good idea to talk to an accountant before you quit and get set-up as a sole trader, or a limited company. I was already set-up as a sole trader as I ran my jewellery business, and I’m so glad I didn’t have to do all that in the first week! As I’ve mentioned MANY times before, an accountant was one of the best investments I’ve made for my business.
  • Financial implications, if you’re looking to purchase a house or go on expensive holidays within the first couple of years of your self employment then you probably shouldn’t quit your day job. Most mortgages require 3 years worth of books to prove your income. And holidays? You’re gonna be working WAY too hard for that ;)
  • Start changing your lifestyle, sure, we all love meals out & trips to the cinema, but it’s a good idea to start thinking of how your lifestyle would change if you quit your day job and didn’t get the big-ticket clients you were hoping for. Having a steady income is incredibly comfortable, something that doesn’t always exist in your first few months/years of working for yourself.

Day One of working for yourself should not be about getting your business ready, it should be about diving in head first with your new projects.

What’s your back up plan?

What would happen if you made no money within the first month? first 3 months? Would you starve? Have to move in with your parents?

  • I gave myself 6 months to turn a decent salary, I can’t remember the exact figure I aimed at but it was my plan to look for part time work if I hadn’t met the aim. There is nothing wrong with supporting yourself financially with a bunch of jobs on the side. It’s not failure, it’s being downright sensible and setting a good foundation for your business and life. Your new venture would absolutely fail if you didn’t have the means to support yourself.
  •  Stay on good terms with your previous place of employment, chances are they’d snap you right back up again if needs be!
  • Remember, it’s really difficult for small businesses to make any decent money within the first year or two, so don’t feel deflated if you’re not making much money to start, just keep swimmin’.
  • Think about multiple income streams – man, I love them so much! How else could you make money? Having multiple income streams means that you’re not completely tied to one branch of your business, so if work dries up a little, you’re still making money from other things. I do this by being both a web designer AND jewellery designer (and, soon, other things).
  • Always have a back-up plan, and keep changing that back-up plan as your business grows.

Now you can think about it…

Now that you’ve been thoroughly scared shitless about quitting your day job… you can start thinking about quitting your day job. It’s not for the faint-hearted, and you need to be really sensible about it if you want to succeed.

Leave a Comment

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

  • ‘quit your day job! live your dream! make loads of money!’

    HAH. I seem to have missed the boat on that one, my motto is more of a “quit your day job! live your dream! do something meaningful so you won’t mind that you’re poor for the rest of your life!” ;)

    Great advice here! :)


  • I’m right there with you. I get emailed a lot from folks who want to quit their job, become a travel blogger and see the world. They’re always shocked when I caution them about that and tell them I worked a corporate job and traveled for years first. It’s not impossible, but it’s not as easy as some make it seem, especially when you have no plan and haven’t thought it through.

    PS Found you through B-School and really bummed you don’t have earlier availability. I’m looking to redesign my site now.

  • I quit my day job after 3 years of being self employed and working a part time job at the same time so I already had a good client base, websites, networks and all the tax stuff in place and I knew I could make enough to live on already but it was still a bit of a culture shock.

    This is great advice, seriously DO look before leaping, test the waters first and, yeah, if you want holidays wave em goodbye for a couple of years!

  • Great post and so refreshing! There is so much madness out there along “if you only believe it, you can achieve it!” lines…

    Having always been extremely cautious & conventional I felt like I was taking a crazy leap when I quite my job in February this year. I guess I probably fall somewhere in between totally underprepared and completely ready… I didn’t have a lot of the things on your list (hello building my own website from scratch in my first week of self employment) BUT I did have some solid regular client work that I knew would pay the bills while I networked and filled my client schedule.

    I think there’s a real balance to be found between not rushing into anything, and equally not waiting until everything is perfectly prepared (which could be for ever). I know for me the tipping point was realizing that I was turning down freelance clients because of the time I had to spent in my day job AND that sticking with a day job I wasn’t into was doing no good at all for my procrastination and general miserableness.

    It’s been just over a month since I took the leap and I’m gradually starting to trust that things will work out and the people I want to help will find me. I also find it helpful now and again to remind myself that my skills (and employability) have grown exponentially since setting up on my own. So if I needed to, I could always go back to full or part time employment in future. (obviously crossing everything that I never have to!)

    Thanks Kim :)

  • I took voluntary redundancy (with an enhanced package!) in November last year.

    My choice was simple; move work location with my old job and give up my business of 8 years as I wouldn’t have time to run it (I was already working 14-16hrs days 7 days a week to stay on top of commitments)…or leave.

    The business was stagnating, there simply weren’t any more hours in the day for me to spend on expanding and I was permanantly reacting rather than being proactive. So as they were paying me to go, I figured it was an opportunity I would be a fool to walk away from, it definitely wasn’t going to be a an option with the next swathe of streamlining.

    Cue a meeting with my accountant for some independant realism and advice, and another meeting with my parents (despite being more than old enough to make my own mistakes!) to get their blessing. I would have done it without that, but it made it a lot easier to know they were behind me in my decision.

    So, am I making more money in the business than before- sort of. I now pay myself an increasing monthly chunk. I have had the time to sort out all the low priority, but necessary jobs to set me up for the long term. I have been planning a huge project for next month which (with any luck- and graft!) will see me in local, regional and industry press…and if I can get on the telly, I surely will! I have the flexibility to do more events, approach more stockists…and subsequently make stock for all these too.

    I have given myself a deadline of September to test this period of my life. I will have enough from my redundancy to last me until the end of the year, but if things dont work out, I will ask to increase my hours at my part-time job (in an offy- 10% discount helps with the bills ;oP) and start looking for better paid part-time work, or a ‘proper’ job again.

    As for holidays…I never had them before so I don’t really miss them! ;o)


  • Great advice! I did something similar – tried out the freelance world for a few years to see how I felt about it, considered my own offerings, saved up a three month buffer, waited until I secured a longer-term contract, and launched my website all before taking the plunge. Doing things this way helped ease a lot of unnecessary anxiety. Although there are still anxious moments as I navigate the world of inconsistent pay cheques, there’s a lot less knowing I waited a bit longer.

  • This is really good advice. I think so many people want to see the benefits before they actually realise how much work it can take to get there.