The Art of Making Difficult Decisons

This is a topic I’ve wanted to write on for a while, as I feel it’s played an important role in my life in many different ways.  A huge inspiration of this topic came after reading the 4 hour work week, where Tim Ferris breaks down the likelihood of potential outcomes that could come from a difficult decision, with a series of questions:

• What is the absolute worst thing that could happen?
• What’s the likelihood of that scenario actually happening?
• What is the chance you could recover 100% from the decision if it wasn’t the right one?
• What is most likely to happen of all the outcomes that could happen?
• What is the best-case scenario if your decision was the right one?

I’ve used lessons from the book and have thrown in my own inferences from personal experiences and will break down some difficult decisions I made in my life.  My hope is that by sharing my experiences with you, you’ll take a look at some of the tough choices in your life and not be afraid to take a big leap of faith.

3 examples of difficult decisions I made:

Back in Nam we decided to buy motorcycles and drive 2000km up the coast… It was a dangerous decision, but we all survived. (This shot was taken shortly after I had rolled into a ditch)

1. Deciding to quit my full-time job to go travelling

After graduating University I knew I needed to get a decent job and begin applying the skills I learned.  Funny enough, my first job offering was to be a DJ at a bar in Vancouver, which had pretty much nothing to do with the psychology degree I had just spent 4 years acquiring.  Either way, I was stoked to be making money, and I went headfirst into the job, putting in my hours, seeing areas I could help and improve them with, and saw a lot of success.  My role grew into an Entertainment Manager, I was given more responsibility, and the company was expanding with more pubs, thus my job’s influence and role grew as well.  After 16 months, I was making a decent salary, had a huge amount of responsibility managing a yearly entertainment budget, and a massive roster of musicians, bands, dj’s, and other entertainers whom I managed and booked across 3 pubs.

Life was going smoothly but a decision was lurking in the back of my mind that would force me to make a difficult choice.  I wanted to travel the world, but I’d need to quit my job and let them fill my position.  This sucked because ideally, I wanted to come back home with the same amazing full-time salary job.  To make the decision, I ran through a few possible scenarios that could happen if I chose to quit my job and embark on a long adventure:

Worst Case Scenario: I come home and have an awful time finding a job, I go into debt and max out my credit cards, I have to borrow money from friends and family to pay rent which ruins relationships, It takes me a couple months to get back on my feet, I go through severe trauma from the whole experience and don’t come out as the same person.

Less Shitty Scenario: I come home and find a job after a few weeks, takes a while to get back on my feet financially, the job sucks, I hate my life, later I decide to quit it and try to find a new one, putting me right back at start.  I’m not making the same money as before and I’m not enjoying life like I used to be, but I’ll survive.

Alright Scenario: I come home and get a job similar to my previous one, I make decent money but still not like before, I have options and room to find something that suits me better, I’m relatively at peace and, for the most part, happy.

Best Case Scenario: I land some kind of dream job, make more money than I was before, I’m even given flexibility to go on another trip and keep the job.

Now after looking at these very different scenarios I ask myself, “What is the likelihood of each one happening?”.  The first two scenarios would suck so much if they happened, but I can already think of ways to ensure they don’t.  For example, I’d reach out to friends while I’m still travelling to line up potential work, I’d get ahead of the ball and know how much money I need in order to give me a month’s pillow of savings so I don’t go into debt. I put aside a few hours a week while travelling to try lining up another job/career for when I get home (strengthen my LinkedIn profile, reach out to potential businesses, ask friends what’s out there and who’s hiring, etc).  After this process I don’t feel so bad about the likelihood of the worst cases.

What ended up happening when I came home was somewhere between the Alright Scenario and Best Case Scenario. I started my own company with the High On Life guys and picked up a few side jobs DJing and doing marketing.  This gave me financial stability as well as mobility and freedom.  Boom – made a tough choice, came out alive and well… onto the next tough choice.

There are plenty of decisions I’ve made in the past that I’ve regretted… but those end up being the best stories to tell anyways.

2. Deciding to fly to Australia alone… with no money.

Through an awesome DJ gig I had booked while travelling with the guys in 2012, I landed a free flight back home to Vancouver, and a one-way ticket to Australia.  My departure date was only about 4/5 months after returning home from our big 7 month adventure, and this led me to an interesting predicament.  I had no money.  Even though I started working right away once I got back home, about 2 weeks before I was supposed to leave on the solo adventure, I had less than 1k in the bank.  So another great difficult decision came my way.  Do I head off to Australia alone on a one-way ticket with barely any money and resources over there, and try to fend for myself?  Or do I let the opportunity go and just focus on working back home.

I had always dreamt of making it to Australia, and that was the initial reason for wanting to start saving up for travel back in 2011, but the stakes were a bit different and not really in my favour, I thought.

I ran through the same worst case/best case scenario routine and figured even if the worst case scenario came true, it’d be one hell of a story to tell and in the end I’d still be alive and ok – so I went.  Upon landing I took a train that dropped me off in Queensland, and went straight to my Canadian friend’s place who was going to school there.  I slept on their futon for what started off as a few weeks while trying to find a job, and ended up turning into a few months.  My two Canadian friends that lived there helped me out and waited until I had a job before asking me to chip in for rent (this helped a lot).  In one week I landed my first DJing gig and 3 weeks later had found myself a full-time commission based sales and marketing job.

I had done it… arrived with no money, got on my feet, and another adventure had begun.  After a few months I had a bit of money saved up and I left Queensland on an epic road trip living in a caravan with 3 other friends I’d met while travelling South East Asia.  We spent the next 6 weeks driving down the East coast of Australia surfing, scuba diving, and exploring.  After my Australian bank account had nearly run dry, I bought my one-way flight home on my credit card and went back to my friends and family – broke.

The biggest lesson I learned from heading out halfway across the world (alone and with no money) had nothing to do about the trip itself, but was learned by the difficult decision I had to make when choosing to go.  I thought about all the things that could go wrong, but I never let those things dictate my decision, and I’m a stronger person because of it.  Sure, a lot of different scenarios could have panned out in the end, and I’m fortunate for my education and networking abilities to have been able to land a job so quickly, nevertheless I was extremely scared to go but I went either way without knowing what would happen. 

Don’t take life so seriously… you’ll never get out alive.

3. Deciding to drop almost everything in my life that cost me money and hop on a very intense savings train, in order to fulfill my dream of travelling.

Another example where I used these principals was when I dedicated 1 year of my life to save $10,000 (details of how I did it will be posted next).  Back in 2011, I had this goal of saving 10k, and to most it seemed a bit audacious, but to me it was a challenge.  When I made the pact to myself to save, I had consciously made several difficult decisions already.  For example, in a typical week, I’d be asked by friends to go out for drinks, go out for dinner, hit the local mountains for skiing, go go-karting, clubbing, wine-tasting, etc… my answer to these 90% of the time was “no, sorry can’t afford it”, “no thanks, I’m saving”, or “can’t, no money”.  Saying “no” became the easy part, but living with myself while always turning down fun activities and things that cost money sucked.  I had created a couple spreadsheets that tracked every dollar that I made and every dollar that I spent, this allowed me to hit my monthly savings goals and make sure I was on track to saving the 10 big ones.  One thing I did to alleviate the pain of always saying “No”, was I put aside a small monthly amount to spend on activities and entertainment, it wasn’t much but when I did decide to spend it on things, those things meant a lot more to me.

My difficult decision of saving for a full year turned into a big challenge for me, because I had to find different ways to still have fun and not spend any money.  I was faced with decisions everyday that were tough, but by ingraining the importance of my savings challenge into every single financial choice I made, I got through it.  I’d ask myself 2 simple questions when faced with a spending choice “will this help or hinder my goal?”, and “do I really need it?”

Start off by taking one small step…

The Take Away Points:

In all 3 of these examples, I went ahead and chose the tougher options, the ones that possessed the highest risk of ending up with awful results and leaving me to regret ever making the decision in the first place.  But in all 3 of these examples, the results were awesome and lead to huge growth and experience.

The hardest part in making a difficult decision is coming to terms with the risk.  But once you’ve looked at the likelihood of the different scenarios, the worst wouldn’t be that bad and the best could be a dream come true.  Once you’re moving forward with any kind of action, you’ll realize every thing’s going to be okay, and even if things don’t go as planned, your ability to regulate the situation and bounce back from your current state is easier than you think.

No action is the worst possible thing you can do.  If I didn’t decide to quit my job and go travelling, if I didn’t decide to leave for Australia broke, and if I never decided to drop my spending completely in order to save for my trip, I wouldn’t have this understanding of action, moving forward, and taking difficult decisions with tenacity and drive.  For me, every difficult decision I’ve ever made has rewarded me ten-fold with adventure, experience, and a big understanding that sometimes the hardest decisions in life will yield the biggest reward.  I dare you to try it for yourself.  Use the Difficult Decision Process to help push you to make a big hairy tough choice.

 The Difficult Decision Process:

1. Write down difficult decision.
2. From left to right, write the worst possible scenario to the best possible scenario that could happen if you were to take action.
3. Think about the likelihood of each scenario and write down the most probable outcomes.
4. Now, write down the many things you could do to fix and regulate your life if any of the worst outcomes happened.  How could you recover from the decision if it wasn’t the right one to make?
5. Take a look at the information in front of you and analyze what you’ve come up with on your own.  Hopefully you’ll realize the worst-case scenario is very unlikely, and the best-case scenario could be right around the corner.

Please note: The difficult decision process should only be applied to certain scenarios in life.  In other words, the decision of getting into a fist-fight may not apply here, nor would being unfaithful or stealing or other ridiculous negative scenarios.  Use this model for areas in life that scare you but would steer you in a positive direction.

Whats stopping you?