If you are reading this, I would like you to pause and think about an obstacle in your life that you are currently facing. Maybe it’s that unfinished book in front of you that you are writing. Maybe it’s a horrible boss at work. Or you are trying to breakthrough in your career but find that you have stagnated in both your direction and growth.

I’ve been there just like you. I have a book that I have been ‘writing’ for over a year now that I have not got around to completing. I have had long days, weeks, even weekends at work where I wondered why I was putting in so much time to do something where I was not sure what the reward or outcome would be. I am all talk about wanting to start a business but have never actually put in the work or taken that first step towards the life of an entrepreneur.

After one of my good friends snagged a copy of this book at a recent book sale and started gushing about the book, I thought that it was time to re-read this book and to learn some of the strategies and tactics to get through the obstacles in my life. Will it work? I’m not sure but I’m certainly going to try to use these strategies in my life.

First, a bit about this book. Ryan Holiday is a former apprentice to Robert Greene who wrote the 48 laws of power and other timeless best sellers – and a lot of how Robert Greene writes his books is inside this book as well. Ryan takes stories and anecdotes from well-known figures in war, politics, history and entertainment and uses these stories as way to showcase how specific obstacle busting strategies were used. Ryan has his own style though – whereas Robert has story after story, Ryan decides to cut this down into something more easily digestible (though that’s not to say that Robert or Ryan is a better writer or has better books). I do love this idea of using the stories of others to emphasize your message or key points in your book though and it makes it real, practical and infinitely useful.

So how do you conquer those obstacles in your life? It involves three keys:

  1. Perception
  2. Action
  3. Will

And what is involved in each of these three key concepts (or at least what are some of the things that I learned)?


Recognize what you can control and what you cannot

Ryan shares the story of Hurricane Carter, a boxer who was wrongly incarcerated for a triple homicide. While he spent time in prison, he was never a prisoner. He would not let others treat him as a prisoner – he did not wear prisoner garbs, he did not eat prison food and he would not do any of the things that other prisoners did. Was this unfair? It absolutely was. But Hurricane Carter recognized his power and controlled what he could in the situation – which was his own perception of things.

A similar story: back when I was working at UBC over the summer as an orientations coordinator, I was working with four other orientation coordinators. I remember multiple times where we were asked by our managers to do certain things that made no sense. While the other orientation coordinators tried to argue their way out of the situation, I put my head down to get to work. Later on, when the performance evaluations came at the end of the short term gig, my managers complimented me on this work ethic – I had recognized that there was nothing I could do about things being ‘unfair’ and the best way to tackle these situations sometimes was to just grin and bear it.

Steady your nerves

One of the worst things to do in a situation is to panic. My favourite sci-fi author, Douglas Adams, wrote in The Hitchhiker’s Guide to the Galaxy to “don’t panic”. This is probably the best advice that anyone can get in a bad situation. When you panic, you can do really crazy things that you will regret later. Maybe you’ll e-mail everyone in the office with a scathing message. Or you will shout obscenities at your partner. Don’t do it! Don’t panic.

I like Ryan’s advice here which is to try Marcus Aurelius’ question whenever you are in a bad situation:

“Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?”

I’m guessing that the answer in most cases will be no. And then you have to act accordingly.

Practice objectivity

Sometimes you have to take a step back on things to make sure that your perspective is correct. Did you get fired from your job because of the economy or was it because you were the worst performer and they were trying to be ‘nice’? A lot of the times when you are faced with an obstacle, take a step back. Look at things objectively. Sometimes it helps to talk to someone that you know and trust and explain the situation to them to get their perspective. With them not being in the thick of things, it might bring a level of objectivity that you need to parse the situation correctly.

Find the opportunity

One of the best things that I learned during my work at UBC was a concept called ‘reframing’. My friend demonstrated this well when giving a tour to potential students at UBC. One potential student, on the tour, saw that there was a lot of construction going on at UBC – roads were being rebuilt and buildings were being built or renovated – this construction caused a lot of disruption to students, not just from the noise but also from detours and closed off walking paths. The student then asked my friend about all the construction that was going on. And a bit of background before I post my friend’s response, UBC students who have been there for a while often joke about how much construction was going on. My friend, without missing a beat, responded with “UBC is constantly improving their roads and buildings”. I have to say, I’m not sure if I would have come up with the same response in that situation but what a way to look at things.

Now I ask you, that obstacle in your life, is there a silver lining? Did that editor turn down your book? Great, now you have an opportunity to write a better one. Did you get turned down for that promotion? Awesome, you have more time to become even better prepared for the next step.


Get moving

Ryan shared a very interesting story about Amelia Earhart. Amelia wanted to be a great aviator but during her time period, people thought women were frail and weak. One day, the phone rang and the man on the line had an offensive proposition, along the lines of:

We have someone willing to fund the first female transatlantic flight. Our first choice has already backed out. You won’t get to actually fly the plane, and we’re going to send two men along as chaperones and guess what, we’ll pay them a lot of money and you won’t get anything. Oh, and you very well might die while doing it.

Guess what she said to the offer? Yes.

Was it the ideal situation for Amelia? Most likely no. But was it something that she could act and build on? Yes absolutely. Imagine if she had declined, she might not have been, in less than five years later, be the first woman to fly solo nonstop across the Atlantic.

Great people act. Great people start. Even if it’s not the ideal situation that they want to be in because let’s face it, we cannot all have perfect situations pop up for us all the time.

Follow the process

This is the same tactic for approaching large or complex problems, and that is to tackle it one small piece at a time. If one of your goals is to write a book, you wouldn’t set your goal as ‘write a book’ for an afternoon. No, if you were smart about it, you would break it down into manageable chunks – coming up with an idea, researching and writing down notes, writing an outline, writing one page, etc.

Here, the advice is to focus on one small step at a time. Maybe your obstacle is to complete 100 pushups – don’t focus on the end goal, focus on doing one pushup at a time. When you focus on one step at a time, you’ll find that it’s much more manageable than trying to tackle everything at once.

Prepare for none of it to work

There are some obstacles that we may face that may be impossible to overcome. Sometimes, no amount of planning or thinking can overcome an obstacle and that is okay! You did your best but think about some of the other strategies here – is there an opportunity here that you may be overlooking? If we face obstacles and challenges all the time then inevitably, there will be some challenges that seem impossible. You are not expected to do the impossible, only your best.


Think negatively

Now, I’m generally a positive person but in some cases, it pays to think negatively. An interesting concept here is that before the start of a project or a complex endeavour, gather the team around and conduct a pre-mortem. You probably already know what a post-mortem is – it’s something conducted to find the cause of death in a person. A pre-mortem is where you assume that the project has failed and you are now identifying all the things that could have gone wrong. When you do this, you will discover many risks that you may not have realized and be able to mitigate these risks ahead of time.

Love everything that happens

Again, being a positive person, this tactic resonated with me – when life manages to beat you down, sometimes all you can do is smile and laugh. And when your enemies see you smiling, grinning and bearing it, you will wear them down. How can someone take things with such positivity? But that’s exactly what you can do in bad situations. In fact, it’s these challenges and obstacles that fuel your positivity.

Something bigger than yourself

In a way, this is slightly about perspective but it is realizing that the challenges are not just about you but it is about something bigger than you. Sure, you might be putting in a ton of hours at work but your project team is probably doing so as well. Some things to think about when you go through challenges:

  • Are you the first one to have gone through this challenge? Probably not – think about others that have been through this
  • Are you the only one affected? Or can you look to a bigger ideal?
  • Can you be strong, not just for yourself but for others?

Thinking about the overall theme of the book, I think we should all be lucky to face challenges and obstacles because in those times that we are challenged, we expand, improve and grow. Just like how a muscle does not grow with ever greater resistance, we do not grow unless we face bigger challenges. And when we face those obstacles, well we know how to deal with them.

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