How I Prepared To Quit the Day Job

The author stands in a greenhouse reading a bookWhen I prepared to quit my day job five years ago, it seemed like a huge risk. Now I’ve been freelancing successfully for two years, I can’t understand why I didn’t make this move much earlier. Digital opportunities mean it’s much easier to work for yourself these days. The flexibility is also a massive bonus, especially as a parent.

I’d been employed in office jobs for over two decades when I first started to plan to leave the office. Although I enjoyed many aspects of company life, there came a point when I wanted to see how I would fare on my own.

Our family life had changed again as my little girl had started school and I was curious to see if I could earn a living from doing the things I enjoyed the most – digital marketing, social media, writing, photography and books.  With over twenty-five years left until retirement, it seemed a good idea to see if I could take time out to find a career that was more satisfying.

I’d already had a taste of freedom during my maternity leave but knew that working for myself would be completely different. For a start, there would be no statutory pay, regular coffee mornings or time to relax.  Our basic costs had to be covered plus we’d want occasional treats too. As for many people, the idea of going independent was just a distant dream, but I couldn’t shake the idea so we started to think about it seriously.

The journey from thought to action took around three years – with many wobbles during this time. Did I really want to give up a solid wage, pension and all the perks that came with my admin job? I liked my colleagues and my employer, but at the end of the day, multiple circumstances encouraged me to take that final step. Here’s how I prepared to quit the day job:

* Note this post includes affliate links (no cost to yourself but I will receive a small amount of commission if you sign up to or buy from them.

1) Asking friends and family about their experience of quitting work

Before I committed myself to serious planning, I found out as much as I could about the reality of quitting traditional work and chatted with a wide variety of contacts.  I was lucky that my husband had taken time out to run his own website business while I remained in the stable job ten years earlier so we already had some knowledge of what to expect. Saying that, our setup had changed hugely since that first break.  Back then we didn’t have a mortgage or a child and we lived in a city so there were significant differences.  There aren’t a wide variety of jobs in our local town so I was aware I couldn’t necessarily jump straight into a like-for-like role if things didn’t pan out.  Because of this I examined my position very carefully over a number of years and actively sought out ways to improve my situation – knowing that if I gave it up, my decision would be a thorough one.

Before seriously preparing to give up the day job, I made a particular point of speaking to those who had recently transferred from regular jobs – especially women with kids because their situation was similar to my own.

The biggest lesson I learned was that it would take time to get established.  For some it had taken at least two years to build to a decent wage and for others, it still hadn’t happened. Rather than take this as a negative though, I saw it as a motivator.  Knowing that I most likely wouldn’t achieve immediate success removed the pressure to perform and encouraged me to reduce my expectations so that they fit the real world. If I hadn’t found this out beforehand then I think I’d be feeling a lot more demoralised now especially when there’s so much hype about making lots of money from self-employment on social media.

I read tons of blog posts promising fast wins and five-figure sums while I was researching giving up my day job but now I realise that most were often designed to sell courses or e-books. I’m sure some of these offer real value (I’m happy to give it a go if someone wants to give me a free place!) but with a staggering choice out there, I felt it best to quiz people I knew instead.  During my conversations, I discovered that several people had returned to the traditional workplace after going it alone because they needed the company of others. This is undoubtedly a factor if you’re planning to work from home.  You need to be someone who’s happy with solitude as you may have to operate independently for long periods of time.  But money is obviously the biggest factor and the greatest obstacle for most. Here’s what we did to tackle this aspect:

2) Living on one wage while working

Unless you have savings or a partner who earns a salary that can support your household, money can be the biggest block to giving up traditional work.

When we began to commit to the prospect of me giving up work, the first thing we did was to review our finances.  I tried various methods but by far the most successful was You Need A Budget or YNAB.  This app allows you to track and catalogue all your expenditure against fixed budgets.  It involves a bit of effort as you have to log every single transaction, but the rewards are worth it. After a few months, we were able to pinpoint exactly where we were spending cash and make savings.  The YNAB software costs $83.99 a year but it’s highly likely that you’ll save much more than this if you use it properly.

Another resource that we consulted is Moneysavingexpert (UK only) which lists all the best tips for saving money via comparison tables, best buys, financial news etc. Again, it takes time and effort to achieve results but if you want to reduce your expenses then this website offers great advice.

Once you’ve scythed your outgoings, you can really start to review how much you need to live on and unless you’ve already been keeping tabs on your finances for a while, I recommend giving it at least a year to chart your expenditure fully.  When you have a realistic picture, practice living on as close to one wage as possible. It depends on your personal circumstances, but I’d also recommend trying to save up at least three to six months of salary if you can. That way if things don’t work out, you can fund any shortfalls until you find paid employment.

A note here – paid sabbaticals are rare these days, but if your employer offers them then this is a great way to explore other options while having the security of a job at the end of the break.

3) Researching ways to earn money as a homeworker

If you have a clear business idea then start planning for this while you’re still employed.  It’s hard to find the time, especially if you have kids, but do all the research you can beforehand and think about your marketing well in advance. It takes time to build a consistent social media presence so the sooner you start the better. Likewise, if you want to re-train, can you do this while working? It can take longer than expected to earn money so try and fit in as much as possible around your nine to five.

I had a rough idea of what I wanted to do, but my aims weren’t totally clear so my back-stop was to look for an online job.  My husband had done this in the past so I knew that it was possible.  I work for Appen * on and off and have been very happy with the way they operate. The projects are short-term, based totally online and there’s no guarantee of continuation but in the seven months I’ve been employed by them I’ve been offered several interesting opportunities.  I love the flexibility of the roles and homeworking is a handy way to supplement your income.  Lionbridge offers similar positions. One word of caution though – it can take a while to qualify for these types of jobs and you’ll have to pass tricky tests so don’t expect to secure work immediately.  Sometimes people wait for months until they get the green light.

Another way forward is through earning money via surveys, mystery shopping and focus groups, but these really do pay peanuts.  You can find more information about them on the Moneysavingexpert Boost Your Income forum board.

Influencing on Instagram is a surprise method that has bought me a bit of pocket money since I first wrote this blog post. I don’t see this as a long term solution though as the algorithm is too prone to change.

I’m only talking about the methods I’ve tried in this section but the world is changing fast so homeworking possibilities are increasing all the time.  You can teach and offer administrative assistance remotely as well.  If you don’t want to work online then you could consider temping work or even part-time jobs to bridge the gap while you develop a new career.

*Note: If you decide to apply through the Appen link above I will receive a small commission.

4) Evaluating working time and space

If you’re going to earn money without the stability of a traditional job, you’ll need adequate time and space to do this.  Time management is one of the hardest elements to nail when you become self-employed so make sure you have enough hours to complete everything. I prided myself on my organisational skills when working in the office, but it’s been much harder than expected to balance the many changing demands of a portfolio career. For a start, things change frequently as new projects come and go, and I have a shorter day because I fit my main routine around the school day. Although I enjoy working late, being on the computer until 11pm at night isn’t beneficial in the long-term as tiredness makes me less productive. That’s just me though – everyone has their own limits – just be aware of your own and make sure you observe them. Here are some questions to consider while preparing to give up your day job:

  • Do you have a dedicated workspace? If not, can you carve out a corner of your living area so that you can establish a quiet zone?
  • How many ‘free’ hours do you realistically have in a day/week? Think about childcare, household tasks, travel etc.  If you give up a regular salary, can you pay for childcare?
  • Do you want to keep your weekends/nights free?
  • Are you good at time management? Be honest and prepare strategies/buffers if not.
  • Are you disciplined? (see above)
  • Do you have someone to support you?
  • Do you have all the equipment you need?

Asking these questions before you give up the day job will help to clarify your goals more effectively.  Be as honest with yourself as possible to save yourself stress and disappointment down the line.  Self-care is as important as hard graft and if you don’t think you can juggle everything then maybe you need more time to put supportive measures in place.

5) Setting modest goals

Last but not least – set those goals!

Without accountability or vision, you may find it hard to stay motivated so write them down and keep them close.

I set five big ones and hit four of them in the first two years – exceeding on two.  One was income-based, one was marketing-related and the others were to do with family and personal health.  I made them measurable and manageable because I didn’t exactly know which route I’d end up taking and wanted to allow room for experimentation. Also, I wanted to stay positive at the start of what I hoped would be a long and exciting journey.

Giving up the security of a day job is pretty scary so although you need to tackle a new life with intention, don’t beat yourself up if things don’t go as you’ve planned.  My year has been full of bonuses and disappointments but I’ve learnt from all of them and as my experience grows, I’ll establish more ambitious targets.

If you’ve reached the end of this post and still feel determined to quit your day job then good for you! Leaving the traditional workplace comes with risk, but if you plan well and take a decent amount of time to consider your future then you should be able to at least take a break from the rat race and hopefully forge a long-term career.

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