Leaving your day job: the things you miss

There are few more liberating (and slightly terrifying) feelings than when you leave big business behind to head out on your own. Give it a while though, and you’ll be surprised that some of the processes you once loathed will become the things you realise had a place. Here's how to set up new processes to replace them, while still enjoying the benefits of working for yourself.

Having an official start and finish time

With the flexibility of self-employment comes the rapid ability for work to creep in to your downtime. Being able to start at nine and finish at five(ish) might end up seeming like a luxury. “You do miss the fact that when you work for a bigger company, you just work! You turn up, do your eight hours, go home and relax,” explains air conditioning specialist Dave Golding (David Golding Air Conditioning). “Working for myself, I am constantly thinking about work at home. I am also invoicing, quoting, looking at plans and chasing money from clients. It doesn’t stop.”

What to do:

  • Adding structure to your day will put some boundaries around work and home life.
  • This can be as simple as making a rule to put away tech devices during dinner time, or banning work-talk on the weekends.
  • Downtime is essential for managing your mental wellbeing. Make sure you take a lunch break and regularly take breaks to stretch and have a few deep breaths.
  • Take the time to enjoy and recognise the benefits of your flexibility. Whether it’s getting the kids from school or banning meetings on Monday mornings, defining what success looks like to you is important, as is celebrating it.

Getting advice and perspective from colleagues 

Asking colleagues quick questions, recommendations, for contacts or even 'been there, done that' anecdotes is an undervalued benefit of working in a larger workplace.

What to do:

  • Find out where others in your network connect. There are many support-based Facebook groups for businesses – everything from helping business women and mums to industry-specific groups.
  • Search on social or ask others who work in the same industry or share similar set ups – i.e they also regularly employ seasonal team members – what sites and groups they frequent. Chances are you don’t have to invent (or reinvent) the wheel, you just have to find out where conversations are already happening and join in.
  • Also check in with what events and seminars are being held near you via the Australian Government’s business website.
  • If you prefer face time to online, create a small business community of your own. Connect with other businesses around you and arrange a regular catch up or knowledge sharing sessions.

Having someone else handle the more complicated financial things

“Probably the single biggest thing I have missed the most is the complete lack of awareness and hands-on requirement for all things related to finances – from setting up management tools to sourcing accounting services, invoicing clients and juggling detailed project estimates,” shares Matt Sterne, partner of creative services duo Two Mad Cowboys.

“It’s a constant and relentless task and I have found myself straddling both worlds as a business owner and creative. I find I am having ever increasing conversations filled with an entirely new vocabulary I barely knew existed, such as 'reconciliation', 'franking credits' and 'dividends'."

What to do:

  • Don’t get overwhelmed – outsource.
  • Align yourself with a good accountant and ask questions when you don’t understand something.
  • You can also reconfigure your regular bill payments to align with incoming payments and 'pay' yourself a salary to maintain some form of structure.

Matt Sterne of creative duo Two Mad Cowboys


Having no one to delegate to

Your receptionist used to organise mail pick-ups and someone always stocked the tea and milk supplies – now it all rests on you. When you can’t work out why the printer isn’t working or how to install a program, you’ll really feel the sting of the loss of the IT department. Lack of infrastructure is a tough one.

“I miss is the all-important administrative and producer type functions,” explains Sterne. “[People who did] everything from research to documentation, processes and more. It’s a wonderful life working as an entrepreneur and business owner, but there sure are many circumstances where an entire team of people can move the world to make things happen. People working together and collaborating, when done right is a beautiful thing no matter if your setup is big or small.”

What to do:

  • Build your tribe! Outsource the things that you struggle with – whether that’s getting your computer tweaked or workplace furniture assembled.
  • Find other businesses that complement yours and talk about teaming up to share resources and extend your customer reach.
  • If you’re regularly sending or receiving parcels, streamline the process using a system like Mailman so it’s less time consuming and stress-free.

Having constant connections with others

You never thought you'd miss the interruptions to your productivity to hear about other people's problems, or even to vicariously keep up with entertainment news. But workplace chat can give you mini 'mental' breaks and a chance to socialise and simple quick snippets of feedback can reassure you that you’re on track and doing a good job.

“I honestly do miss the social aspect of working as I made such strong connections,” explains former childcare centre worker and now part-time nanny, Brooke Day-Herbert. “It was also nice to have a room leader to guide me and make comments on how I was doing. I thrive on positive feedback and constructive criticism as I am always doubting myself in my job practice.”

What to do:

  • Start with the small things that will add a boost to your day. Chat to your local barista about whipping up your preferred coffee at the same time each morning so you have that personal touch.
  • Carve out regular social media ‘check in’ times to have a ‘friend’ hit. Time it with your mid-morning coffee or afternoon snack – just don’t stay logged in and distracted all day!
  • When the end of the week hits, a shared glass of wine or beer is also a shared celebration of hard work and a chance to signal a break. Replacing the 'end of week' sign off is important if you want to create some structure around work and home life, and to remind yourself of what's been achieved that week, along with avoiding the 'Groundhog Day' feeling.
  • Rally a group of self-employed friends or contacts and use it as a networking and social event - catching up for a BYO drink at a local park beach, bar or pub.

5 quick things to consider before you start out

1. What boundaries will you set between work and life?

2. How long will your rainy day fund support you and your business?

3. Who is part of your support tribe?

4. What services (https://www.officeworks.com.au/services) can you outsource?

5. How can you connect with others in similar situations?