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How to handle the emotional rollercoaster ride of being an entrepreneur

Monday, 8 July 2013 | By Jonathan Weinstock

As an entrepreneur, sometimes it feels as if you are getting kicked in the guts from every angle!


As your journey progresses, the more issues you face, the more experience you gain and the better you start to handle situations – but then a whole bunch of new issues can arise. The rollercoaster continues.


The ability to keep the calm and the ship afloat sailing in the right direction is a key skill of a leader.


One of the positive comments I used to receive when I captained a cricket team was my ability to ‘keep the calm’ under pressure and make the team feel confident in their ability without a fear of failing.


If the leader panics, how do you think the followers feel! The best sport coaches and captains know how to handle pressure situations, and navigate through unfamiliar territory while keeping the troops in check, motivated and inspired to perform – even if they have to bluff their way through.


When the heat gets turned up, how do you react?


Here’s a depiction of the emotional rollercoaster of a newbie to entrepreneurship:




The ups and downs can be quite steep.


Sales can be ripped from right under your eyes when you think you’ve made a sale, and then all of a sudden, the hard work you’ve done has gone to dust!


What about when a star employee with whom your business is reliant on, walks in, resigns and then sets up in competition while breaching restraint of trade clauses?


What about the legal letters you receive for an ambit claim?


What about the frustration when your IT guy doesn’t respond and you have excessive down time and no one has email or internet access for long periods?


How do you feel when you fall behind on ATO payments or need to find cash for payroll next week?


What do you do when most of your customers decide to stop buying and don’t need your service anymore?


What do you do when you find you have been defrauded by someone you are paying over $100K salary to?


Take a deep breath and smile? Maybe a walk around the block, or punch out a session at the gym. Or do you pull out the bottle of whiskey! Everyone has a method, but I recommend the healthy lifestyle over a pack of smokes. Water, sleep, exercise, massage, meditation, breathing, self-help books, talking with peers, counsellors, professionals or mentors are my form of dealing with adversity and of course – smile!


These are real day-to-day scenarios that all of us have faced, or will face, at some stage of our entrepreneurial journey. It is bizarre when you come home and your spouse says, ‘How was your day honey?’ and you wonder whether to reply ‘just another day!’ Some people just can’t comprehend the level of stress and pressure an entrepreneur faces on a day-to-day basis.


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That’s why one of the greatest things I’ve done in my life is join The Entrepreneur’s Organisation six years ago and I have been a very active member and huge advocate since. Each member across the globe lives and breathes the same values and issues across business, family and life as a whole.


So, my philosophy on the rollercoaster ride is simple: The more often you get kicked in the guts, the stronger your guts become. A great entrepreneur is someone who has encountered much heartache and pain, equally as much as success, in my opinion.


Some are made with stronger guts than others based on their upbringing, although most people have a soft inside, which is why they don’t make the cut in business and 80% of businesses fail in the first five years.


Now here is how the rollercoaster ride looks once you’ve gained a few battle scars:




It’s a whole lot more mild.


You don’t feel the bumps as much. It’s, relatively, a walk in the park; although no day is ever a walk in the park! Nothing seems to surprise you. You come ready for battle. Your guts are now so much stronger that you feel you can handle more risk and even bigger surprises.


That’s where good mentors and leaders come in handy. They already have the battle scars. They’ve ridden the ups and the downs and can predict what lies ahead. They see patterns that inexperienced entrepreneurs don’t see and are often perceived as magicians! They can map out the course and know when the next bump is coming while knowing who to call when they stumble on an unforeseen bump.


They don’t teach this at university, but they should. I should start a subject for all business students called: “Expect the unexpected – handling the ups and downs in business.” People need to learn how it feels and then how to act, and this helps build resilience.


If someone says they have never failed, they are lying. While the great leaders and sportspeople may have achieved great success, their journey is full of bumps and scratches and their ability to overcome adversity and stay focused is what stands out.


This is the huge risk of putting someone with limited experience as a leader in a company or as captain of a sports team. I don’t like seeing 21-year-olds being made captain of an AFL club or a state cricket team. Sure they are great athletes, but as leaders with limited experience, I find it hard to believe they have ridden enough death-defying rollercoasters.


One of my young partners in a business came into my office the other day feeling stressed and I said, “I can tell which rollercoaster you are on.” He looked at me a bit funny, but then I explained what I’ve just written about. There’s no quick fix. It takes time and experience to smooth the bumps and I can appreciate and sympathise with the ride.