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Unleash Your Life: How To Achieve Big Goals With Trello

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This blog post is part of the Trello Day Replay series of talks given by members of the Trello team, Google, and Typeform about different ways they’re using Trello to be more effective in life and work. For more inspiration, check out the rest of the talks here.

There is a self-destructive force that prevents artists, entrepreneurs, and hustlers of every sort from doing their most important work. The bad news? Everyone experiences this force. The good news? It can be managed.  

Two-and-a-half years ago, this negative force hit me like a prize fighter. It tried to demoralize me. It tried to stunt my growth. If it had succeeded, it would have completely changed the trajectory of my personal development, and thwarted a sport that’s become an exciting, new part of my life.

Climbing Over Doubt

I’ve been an outdoorsman all my life, but as I’ve grown older, I’ve spent less and less time in nature. In April of 2016, a friend invited me to climb The Grand Teton, a classic alpine peak located in Wyoming with an elevation of 13,775 feet.

I enjoy hiking, but at that time I had barely climbed above 9,500 feet. This was going to be a big step outside of my comfort zone. However, I felt a life inside me that wanted to come out—a life that had been suppressed.

I accepted the invitation, created a Trello board, and started preparing for the August climb. I made a reservation with the guide service and paid a deposit. I started shopping for equipment and began training. All was going well until the initial excitement wore off, and pessimistic voices started stirring in my head. They sounded like this:

“You’re not a mountaineer.”

“This trip is too expensive.”

“You’re going to be a new dad soon. It’s too risky.”

At first, I ignored the voices, but they got stronger and stronger until one morning I acted on them. I picked up the phone and called the guide service, intent on cancelling my reservation and refunding my deposit.

As the phone rang, a part of me felt crushed. As it continued ringing, a part of me hoped no one would answer. No one did, so I hung up. The next morning, I dialed the phone again. A part of me felt crushed that I had resigned, but once again no one answered.

Why did I do this?

I was over the moon to accept my friend’s invitation, but then I fell back down to Earth where I preferred the known over the unknown, the comfortable over the uncomfortable, the couch over the trail. I didn’t know it then, but looking back on it, I was being attacked by Resistance, with a capital R.

In The Face Of Resistance

Resistance is the term used by Steven Pressfield in his book The War of Art to describe a self-destructive force that prevents people from doing their most important work.

At first, Pressfield thought the force only applied to him. Then he thought it only applied to writers. Finally, and with input from others, he learned it applies to everyone.

Maybe you’re an artist who doesn’t create art – like a writer who doesn’t write, or a painter who doesn’t paint, or an actor who doesn’t act.

Or maybe you’re an entrepreneur who never starts a venture.

Or a citizen who wants to run for public office but never sees your name on the ballot.

We all have our callings, our duties to become higher versions of ourselves. And unless I’m way off, there’s a small voice in your head piping-up to remind you of your calling the way it has a thousand times before. Chances are, you’re no closer to acting than you were yesterday, or will be tomorrow. This is how you can change that today.

“Your chances for success will increase dramatically when you search intently for reasons to go up instead of inventing reasons to go down.” – Steve House, Scott Johnston, Training for the New Alpinism

The Symptoms Of Doubt

Resistance is internal, so although it may seem to come from external sources like bosses, spouses, or children, it doesn’t: it comes from within you.

These symptoms of doubt include:

  • Unhappiness: You’re bored, you’re restless, you feel guilty but don’t know why.
  • Self-doubt: You question your desires,  and your abilities. Are you being authentic if you pursue them?
  • Criticism: You’re critical of yourself, and may even be critical of others.
  • Distraction: You’re consumed by meaningless content, clickable headlines, and binge-worthy television.
  • Shallowness: Your actions are empty or trivial.

All these symptoms are rooted in Fear, however, the granddaddy of all this negativity is Procrastination. And Procrastination has a voice. It’ll tell you anything to keep you from doing your work, and it’s really good at rationalizing. Procrastination sounds like this:

“I’ll do my work. But first I must check my email, or Facebook, and I have to clean my desk.”

It also sounds like this:

“I really shouldn’t work now because I have to go to my kid’s soccer game. What kind of parent am I if I miss it?”

After all, we don’t tell ourselves, “I’m never going to write my book.” We say, “I’m going to write my book; I’m just going to start tomorrow.”

Tame The Doubting Dragon

Now that you know a little bit about Resistance, how can you manage it?

There are four things you can do:

  1. Be conscious of it. If it helps, you can envision it as an adversary, or an enemy, or dragon that needs to be slayed.

  2. Learn to recognize the voice of Resistance inside you – so you can dismiss it.

  3. Navigate by Resistance. The more symptoms you feel about doing something, the more important the work.

  4. Make a start. This is the hardest thing to do because remember, you don’t tell yourself that you’ll never run a marathon; you say that you’ll start training tomorrow. 

Bestselling author Og Mandino encourages us to consider the lesson of the firefly who gives off its light only when in action. You can make a start. This is where Trello can help.

“Never put off until tomorrow what you can do the day after tomorrow.” — Mark Twain

Achieving Your Goals and GTD With Trello

During my Trello career I’ve had the privilege of speaking with hundreds of customers, many of whom use Trello with the Getting Things Done method. The GTD method emphasizes moving projects out of the mind, recording them somewhere externally, and breaking them into actionable tasks. There are four steps:

  1. Find a collection tool or a device that helps you capture ideas. Collection tools can be analog, like a journal, or they can be digital, like a Trello board.

  2. Clarify what you want. The challenge is to do this in one sentence. Albert Einstein said, “if you can’t explain it simply, you don’t understand it well enough.”

  3. Decide the next steps that you need to take.

  4. Set reminders that you can regularly review.

Implementing GTD 

Ultimately, I climbed The Grand Teton, which lead to a second invitation from my friend, this time to climb Denali, the highest peak in North America with an elevation of 20,310 feet. I accepted the invitation but soon thereafter the familiar voices started:

“You’re not a mountaineer.”

“This climb is way more expensive than the last one.”

“You should spend time with your wife and daughter instead of pursuing your own selfish interests.”

But this time around, I was prepared. Let’s explore how I fought the resistance with my Trello workflow and GTD, or Get Things Done, methodology for my Grand Teton to Denali success.

1. Find A Collection Tool

Trello is my collection tool, so I create a Trello board.


Pro Tip: There’s power in visualization, so pick a board background that helps you visualize your calling.

2. Clarify What You Want In One Sentence

I create a list and call it “Motivation and Resources.” In the list I create a card – I call it my “Why?” card – and here I write my sentence.

This sentence changed several times during my Denali preparation as I considered why I wanted to climb the mountain. This is the most important card on the board, so it’s worthy of further explanation.


Just like the power of visualization, there also is power contemplating why you want to do something. Simon Sinek wrote about this in his bestselling book Start With Why.

Most of us start with the “What”. In my example, I want to climb a mountain. But what really drives success is the “Why.” Because the “Why” elicits emotion – and emotion is more powerful than reason. When you make a decision based on a strong “Why” you’re sold, not on your idea but on the cause of your idea. And you go above and beyond to support the idea with your time and resources.

Pro Tip: The Read-Me Power-Up is a pop-up that appears when you open a Trello board. Here you can write a welcome message or instructions for how to use a board. You can adjust the pop-up so that it loads whenever you open a board, or only when opening a board for the first time. This is a great place to post your “Why” sentence.


3. Decide Next Steps

I create two more lists: “To Do” and “Done”the idea here is to move completed cards from one list to the other.

Pro Tips: 

  • One thing that makes Trello such a great collection tool is its mobile and offline capability. You can create “To Do” cards whenever you’re inspired and wherever you roam.
  • When making “To Do” cards, don’t make them too general. For example, if you’re writing a screenplay, don’t create a “To Do” card that says, “Finish Screen Play.” Instead break-down the tasks necessary in order to complete the project. Create “To Do” cards for the inciting incident, the ending, the theme, the subplot, etc.

4. Set Reminders


Have you ever had a flashlight with dead batteries? When does your brain remind you that you need new ones? When you try to use the flashlight and notice the dead ones!

This is why we set reminders.

When you create a “To Do” card, ask yourself, “When do I need to see this card again?” and add a due date to it. If you don’t put a reminder in place, your mind will keep pressuring you about the open task, which will add to your stress.

A Quick Recap To Managing Resistance

Let’s recap the four steps to manage Resistance:

  1. Be conscious of Resistance and know that it exists—if it helps, think of it as an adversary, or an enemy, or a dragon that needs to be slayed.

  2. Learn to recognize the voice of Resistance inside you so you can dismiss it.

  3. Remember that you can navigate by Resistance. The more symptoms you feel about doing something, the more important the work.

  4. Make a start. This is the hardest thing to do but it’s also where Trello can help:
    1. Find a collection tool that you’re comfortable with.
    2. Clarify what you want in one sentence.
    3. Decide the next steps that you need to take to get the ball rolling.
    4. Set reminders that you can regularly review.


Setting The Right Expectations

So, what can you expect when you do all of this?

Frankly, you’re not much closer to your desired outcome, whether it’s writing a book, or starting a business, or climbing a mountain. However:

  • You switch from a consumption mindset to a creative mindset.
  • You switch from a fixed mindset to a growth mindset.
  • You gain clarity on what the project really is about and the associated next steps.
  • You build trust in a system for collecting ideas, projects, and tasks.
  • You free your mind from To Dos, which reduces stress and helps you think more productively and creatively.

There’s something else you can expect, something that Scottish mountaineer W. H. Murray describes as follows:

“Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred.”

Providence moved me in the spring of 2016, when I placed two phone calls that thankfully went unanswered, and as a result, set me on a new and exciting path.

So where will a divine intervention move you?

At this very moment…

  • There are countless artists who are updating Facebook instead of writing prose, or stirring paint, or memorizing lines.
  • There are endless entrepreneurs who are posting business articles on LinkedIn, rather than getting to work.
  • There are hordes of citizens who are arguing about politics, rather than getting involved.

Which Mountain Will Your Climb?

When you reflect on this post will it have been a waste of time, or a catalyst to move toward your most important work?

You’re on the precipice of an amazing opportunity right now. Congratulations!

Why we choose the comfortable over the uncomfortable—how to slay the dragon of doubt step-by-step to achieve big goals using @Trello. #TrelloDayReplay

I wish you nothing but success. And I I hope you slay the Dragon – and Unleash Your Unlived Life!


Want even more inspiration from Trello users and team members? This blog post is part of the Trello Day Replay series. Check out more talks here.

Good or bad, we'd love to hear your thoughts. Find us on Twitter (@trello) or write in to support@trello.com

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