THE BLOG
01/08/2016 04:20 pm ET Updated Jan 08, 2017

Too Closed for Comfort

Do you secretly dread downtime? How can entrepreneurs, whose work is largely their identity, cope with taking a holiday?

A few years ago, the idea of heading on holiday would have sent me into a complete panic. My mind would wander to wondering what on earth I would do outside of the pumping, heart-racing, hard-but-totally-awesome, 100-per-cent-satisfying place that is called my office.

I'm sure I'm not the only entrepreneur who has ever felt this way.

We love the concept of a holiday and dream of hours by the pool, of running away to a villa in Spain, escaping to the Tasmanian wilderness sans phone reception or cruising the Greek Islands and getting lost in the Aegean sunset. BUT when it comes to actually doing it, we often... can't. It's really not that we are so busy we can't get away, instead we're secretly afraid to.

If your identity is largely wrapped up in your work, then the prospect of spending a chunk of time away from your desk can conjure up the most incredible (and sometimes unexpected) emotions - like fear (you could miss a big deal or opportunity while you aren't there), guilt (you could be off loafing around when some of your staff might be working), stress (how would you even approach the backlog of emails on your return?), anxiety (just imagine the size of your to-do list on the first day back), wonder (at what exactly you'd do on holiday to keep your mind inspired) or deeper thoughts of uncertainty (who are you, really, when you're not working?) or avoidance (you don't want to face the reality that you don't really have a life outside of your work).

We can be a complicated lot at times, and quickly sink into this abyss that's often mistaken for hard work, when really it means so much more.

But last year as the question of Christmas closure rolled around, it was different. Profoundly different. I didn't feel a surge of panic; instead I felt a burst of excitement. Would I cruise up the coast to my second home of Bangalow and pick avocados with my mum and collect shells with my niece? Or would I take that friend up on their suggestion of travelling to Cuba for New Year's?

It's a dramatic shift in mindset for someone who has been a workaholic in days gone by, even with the best of intentions (my grandfather instilled in me a very stoic, hardworking attitude and I have always believed in whatever I was doing wholeheartedly).

This change hasn't been accidental but, like most things in life, I had to action strategies to make it happen. Firstly, I got very honest with myself about it (I had that frank self-sabotage talk and the subsequent, "You've let yourself wander off track" talk), then I looked at my motivations (asking myself why I worked so darn hard and if it was really necessary) before pinpointing areas of weakness (like going back to the office to work after speaking gigs, instead of just picking up my dog, Benny, and heading home).

Then I began to intentionally fill up my life with non-work things. It's that last point I want to expand on here. If you're an entrepreneur or anyone from any profession who secretly dreads downtime, then try these. They have helped shift my approach and energy around being off-duty immeasurably.

1. Have an open door policy...
At home I currently have someone's cossie hanging from the shower rail in my ensuite bathroom. I don't know whose it is and that makes me smile, because it's exactly the kind of random, spontaneous, magnetic environment I want to create at home. But it hasn't always been this way. Four months after moving into my new house this year, I had a realisation - the building I slept in was nothing more than a shell. Despite the fact I constantly talk about having an open-door policy in my office, when it came to my home I hadn't created a warm, inviting, energetic environment at all. I realised that, for me, a house is not a home unless it has a flow of people passing through it, filling the rooms with chatter, laughter and positivity. I started to invite friends for last-minute dinners. I asked girlfriends over for sleepovers, I told surfer mates they could leave their boards on my balcony. I offered my spare car spaces to beach dwellers. I let some team members house-sit when I was travelling.

2. Don't glorify isolation
I think it's very easy for entrepreneurs to start to accept that a sense of isolation is just a side-effect of our profession, along with sleep deprivation and 'iPhone elbow' from checking emails in bed (how many times this week have you dropped your phone on your face?). When we are 'on' we're so busy constantly talking, connecting and brainstorming that by the end of the day, we just want to zone out in front of the TV and hide ourselves away. Don't get me wrong - I value alone time and think it's vital to avoid burnout, but I also don't necessarily think it's healthy to put yourself in a bubble night after night.

If your work calendar is full, you might need to be intentional about your personal one. It could be as simple as searching meetup.com for one event per month in your area that interests you. Think about starting your own book club, walking group, handstand gang, whatever! I doubt that the activity you enjoy is so obscure that no one else in your area enjoys it too. It just takes a bit of courage to reach out and connect with people and they probably feel as isolated as you do.

3. Set work-(un)related challenges

If you have two weeks off work, it's the perfect time to set yourself a personal challenge. But don't worry, it doesn't need to be a muscle-aching, back-breaking CrossFit-style endurance test! It could be a personal project that helps you embrace a new hobby, reconnect with an old friend or just get better at a craft. If you need inspiration, watch the TED talk by Google engineer Matt Cutts entitled "Try Something New for 30 days". Back in 2009, Matt felt he was stuck in a rut so he vowed to walk 10,000 steps every day for one month.

Other 30-day challenges he attempted included following a vegan diet, learning to play the ukulele and doing something nice for his wife every day. For motivation, check out 30dayschallenges.net, an online forum where people share their personal missions. It might not directly boost your business, but it may boost your joy.

4. Say yes
One of the best shifts that has come into my life of late is making 'yes' my default instead of 'no'. So when I'm asked to go to the beach, to the park, on a holiday, out for lunch or over to someone's place for late-night pizza and a soppy movie, I force myself to question why I shouldn't do it, before I say no. I'm not advocating burnout or getting yourself so busy socially that you are exhausted and even more stressed at work because you have limited capacity. What I am suggesting is that you simply stop yourself and say, "Why not?" before you say anything else... and just see what happens. Not only does your entire mindset shift, but you'll open yourself up to a host of fun, incredible things that can slowly shift your gaze towards life outside of the office.

5. Get some help
If you are really struggling at work, look at the numbers and see if you can get some extra help for yourself. Entrepreneurs always put themselves last (case in point: we always pay ourselves last and only if there is any money left!) but it might be time to put yourself first for once, which can help take the practical pressure away so you feel you can have some time off and that life won't be hell on your return. My tip: hire someone with a strong, but nurturing personality so they can not only help you diarise your appointments but are discerning enough to buy you milk when you need it or book a holiday when they can see you unravelling. Or, if you don't feel you have the tools to help yourself and a PA isn't enough, don't be afraid to get a professional or two in your camp to help untangle the mess, so you can free yourself and enjoy the sunshine again.