top of page

Where Entrepreneurs Go To Let Down Their Hair

Climate change is making you nervous, but let’s face it, the globe hasn’t warmed enough to make winter in Toronto completely bearable. You want a vacation; but how can you possibly get away from your business without chaos erupting in your wake? And where would you even go, a sensory deprivation gulag where you won’t be tempted to check work messages every 5 minutes?

First of all, know that ‘entrepreneur’ and ‘vacation’ are separated by more than 16 alphabet letters; holidays are just wishful thinking to many small and mid-size business owners. If you have put your heart and soul into your startup, you may feel that no one could possibly fill your shoes, and that problems would pile up so high in your absence that you’d never catch up. Well, let’s hope that’s ego talking! Because if it’s true, then you’ve boxed yourself into the kind of slavery you were trying to avoid when you struck out on your own in the first place.

The fact is that time off is essential, not just for your own physical/mental/emotional/spiritual health, which you probably neglect in favour of spreadsheets all the time; having some leisure time will actually make you a more effective spreadsheet-analyzer. You won’t be stressed, sick, burned out and unhappy, which are all things that overworked entrepreneurs experience even when things are going well.

How connected you want to be to your business during your vacation is really up to you, though we do have some helpful tips to make sure the business runs smoothly in your absence. Whether you decide to slip away for a long weekend or cancel all your prospecting for the next month, here are our top 5 vacations for the deserving entrepreneur (hint: all entrepreneurs deserve a vacation!)

  1. Palm Springs. With stunning mountains, canyons and trails, this warm-weather destination is a lot sleepier than the rest of the Top 10 US travel destinations for 2015, but sleepy is good, and so is nature, especially for those of us who spend most of our lives staring at a smart phone while breathing humid exhaust in The 6.

  2. Rome, Italy. One of the birthplaces of modern Western civilization, thought, and yes, commerce, the Italians know how to get things done, they just do it differently than we do…a fact you can contemplate while drinking a slow glass of red wine in a sidewalk café while you gaze at breathtaking architecture.

  3. Cancun, Mexico. This inexpensive resort heaven is perfect for families – and after all, you probably spend more late nights at the office than you do with your family, so now’s the time to make it up to them. Bonus: you can stick the kids in a Kids Club while you enjoy a lobster dinner with your long-suffering partner.

  4. Andhra Pradesh, India. Who-what-now? If you’ve never heard of this state, it might surprise you to know it boasted 200 million tourist visitors in 2012, drawn to its incredibly rich temples and pilgrim centres, ancient caves, spectacular golden beaches and stunning architectural monuments. On the less spiritual side, India is also a huge commercial centre, which might give you some opportunities to go global with your products and services.

  5. Montreal, Canada. Sure, you took that middle school field trip (all you remember is pulling maple syrup candy) and a couple of drink-a-thons at the pubs with your Carleton U friends, but you’re all grown up now…and Montreal has wonderful gastronomie, plenty of diversions and sights to occupy your down time, an expanding economy if you’re looking to grow your business – and best of all, you don’t even need a passport.

A final word on vacations for entrepreneurs: Don’t just lock the door and walk away, leave somebody you trust to be accountable while you are away. Remember, giving your staff or business partner an opportunity to step up their game is a good thing. Away from your watchful eye, they will probably relax - and as a result, they will emerge stronger, more confident, and better able to help you with the day-to-day running of the business.

Photo credit: Wee Vacation

bottom of page