A Career Coach on the Transition from 9-to-5 to Working for Yourself


You're on your own time now.

Woman walking outdoors.

Ed’s note: This post was written by guest editor Jo Green of Jo Green Coaching.

Transitioning from 9-to-5 in an office to making my own hours was one of the toughest things about going solo. Like most people on the brink of business ownership, I’d read lots about the pleasures of living the freelance dream. Working in my slippers, knocking off at lunchtime on Fridays, and popping to the uncrowded supermarket during others’ peak work times definitely appealed.

One thing I discovered is that while there are a gazillion shiny stories about the joys of working out of your local ‘coffice’, the downside of the shift to solo operating gets much less air time. Advice on managing zero boundaries to working 24/7 hardly gets a mention. Nor does the lurking guilt that hits when your working day slips below eight hours (who made that rule, anyway?). Finally, there’s the sorry and under-reported fact that while your cat/dog/wall may talk back occasionally, they’re generally not up for a sustained conversation.

One of the first bits of advice I tried and failed to follow suggested writing down your ideal week. This was hugely confronting. I felt I had to pin down and schedule the perfect mix of everything in my life – relationships, health, business, learning, hobbies, etc. Figuring this out was just too daunting. So I gave up on that.

Since then, I’ve learned lots about how and when and where I work best. I’ve learned to balance the competing demands on my time and energy in (mostly) sane ways.

Here is what I suggest:

1. Find your daily rhythm

I work most productively in the mornings. I start my working day with marketing, administration and writing jobs that tend to go well first thing. If I left these often ‘less absorbing‘ tasks until later, my natural capacity for procrastination might set in. By the afternoon, I’ve got that satisfying feeling of accomplishment that comes with getting stuff done. This is a great time to be really present for clients.

Observe your energy levels throughout the day and work out your best times for focusing on different things. When is it best to exercise, do admin, see clients, be creative or take time off? Working to your natural rhythm most of the time makes you more efficient, settled and productive.

2. List three things to do

Some days, I seem to switch to ‘autopilot’. I work through one task after another getting things done, without prioritising what really needs doing. While I’m ‘knocking off’ routine jobs, somehow I’m not satisfied at the end the day.

To beat this feeling of automated underachieving, try starting your day with clear intentions. Write down three things that you will get done. Add some reciprocal accountability by exchanging ‘three to-do’ texts with a fellow freelancer or business-owing buddy. Sorting my three things makes me feeling great. Not only that, this deceptively simple bit of mindful planning has a bonus flow-on effect making me more productive and focused throughout my day.

3. Schedule social time

If you work from home or in a small office as I do, you can go a whole day without interacting socially with another human. Even for introverts like me, there’s a limit to how much quiet time alone I can healthily handle! This (literally) hysterical clip contains a warning about the potential pitfalls for all of us who work from home.

a) Hang out with other solo business owners

Social time is extremely important for prevention and cure of Entrepreneur Flu. Chatting honestly to like-minded solo workers really helps to normalise what you’re experiencing and halves the problem. It is also a chance to share business advice, grow your network or simply bounce ideas. Finally, it’s also the time to sing the praises of our flexible entrepreneur lifestyle – as a friend and I often do!

b) Be with your nearest and dearest

I work two evenings a week. Without our regularly scheduled ‘before work’ coffee dates, I could go days without a proper conversation with my husband.

One of the perks of working for yourself is the luxury of scheduling your own time. Take advantage of this to book lunch with a mate who works near where you’ve got an afternoon meeting. Make a catch-up call to a friend on their lunch break.

While coaching offers brilliant two-way learning, it’s also one-sided. I love hearing all about someone else and supporting them in what they are doing. They talk 90 per cent and I talk 10 per cent, so sometimes it leaves me needing to regroup and recalibrate by nattering away to a good mate. I aim for one personal human interaction per day – this might happen by design with my personal trainer or maybe by accident with my hairdresser. I also aim for at least two social chats during ‘normal working hours’ each week.

4. Schedule self-care

The risk, responsibility and downright loneliness of running your own show can be overwhelming. Sometimes you need to ditch that ‘to do’ list and take extra care of yourself. Day to day, I know that if I take time to care for me, I’m a much better coach. I work on finding self care that fits my ‘office hours’, including exercise, healthy cooking, walking by the water, cat cuddles and chatting with mates. Working in the evening means I also need to take a break in the day so I’m not doing marathon 12-hour stints.

5. Look backwards and forwards every Thursday

a) Fill your ‘Win Jar’ Review what you have achieved for the week and celebrate wins of all sizes. Write these gems on pieces of paper and put them in a jar. On a bad day, empty them out and remind yourself of how much you have done and how brilliant you really are!

b) Check your diary for the next week Is it totally jam-packed? If you feel you’ve crammed in too much, move some things about. Make sure you’ve scheduled in some self-care and social time.

6. Find your boundaries

Make the most of the autonomy that comes with running your own business. Most times you don’t have to be at others’ beck and call, so set your own sensible deadlines. I love to finish my day having done the things I set out to do. This beats working myself to the bone because I’ve taken on more than I can elegantly acquit in my available working hours.

Finally, a word on the potentially vexing matter of hours, who decreed we should work eight of them consecutively for five days a week? I suggest you find what works for you and stick with that.

Jo Green, career change coach

I know how it feels to be lost in your career. That’s why I coach, to create learnings, action and help others get stuff done. Changing your career can be lonely and confusing, so I’ll walk alongside you, be your cheerleader and help you figure out what meaningful work is for you.

Visit jogreencoaching.com

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