Two questions that will wreck your day
(in the best way possible)


By Tim Schuster

Can I ask you two questions that have absolutely wrecked my life in the best way possible?

These two questions are at the heart of deciding what you want to do with your life – and discerning whether founding a non-profit is for you. (Actually, these questions are about discerning the undertaking of anything worthwhile, creative, adaptive, new, missional, or innovative).

Not only are these two questions vital to our well-being, what I’ve come to observe is that if we don’t wrestle with these questions we are at risk of wasting our time and energy going down a path that could hurt the people in our lives.

Not being clear on these questions can result in unmet expectations, which always leads to anger. You may feel taken advantage of – bitter even. We can avoid despair with these two questions. You may feel like you didn’t get what you signed up for. The anger will – like anger does – spill over into the key relationships in your life.

In other words, it’s only a little bit about you: Wrestling with these questions is about you, but it’s far more about the people in your life and the people you want to serve.

(Also, these questions are about money, vocation, calling, power, technology, time, energy, health, community, energy, and careers.)  

The two questions are this, asked in this order: What do you want most? And what are you willing to sacrifice to get it?

QUESTION #1: What do you want most?

When you put your finger right on it, what do you want most? What is your calling? What lifestyle do you imagine? Who are the people you want to change? What do you want to put your hands on and your mind to? What systemic change are you working for? What industry are you disrupting? What identity, position, title, or story of success are you telling yourself?  

I like this question. It invites me to think big about what exactly I’m doing in this world – and how I want to use my limited time.  

That is the first question. Consider this an invitation to be clear on your goals. But there is another question. And now you'll see why it's asked after the first:

QUESTION #2: What are you willing to sacrifice to get it?

What are you willing to give up? What cost do you deem to be worth it? When you think about what you want most, what are the things that are definitely non-negotiable? What values are not for sale? What relationships will you fight for?

These two questions – asked in this order – are so vital to a life of balance, healthy expectations, and clarity of personal calling. In essence, in so many cases, we can have whatever we want – but in many cases we can’t have it all.  

I want to build a successful business, but not at the cost of my health or my family.

I want to start a non-profit, but I’m not willing to sell my house.

I want success, but not at the expense of family and friends. 

I want to plant a church, but I refuse to lose my joy.

I'd like to overcome an addiction, and I'm willing to find new friends. 

I want to start a photography side-gig, but Sunday afternoons are off-limits.

I want to travel, but credit card debt is a BIG NO.

Healthy Tension

When we put these two questions into a healthy tension, we begin to see a new perspective emerge. New boundaries take root. Priorities come out of the woodwork. Our full humanity – in our limitations and our possibilities – emerge. We start to realize that we need others along for the journey and that it’s okay to not be the hero all the time. And, mostly, we create healthy expectations and live according to our deeper values.

And, of course, we’re never done wrestling with these questions. Very rarely do we arrive at a perfect balance, which was never the goal. But rest in the fact that it’s the right kind of healthy and vibrant tension. So, what do YOU want most and what are you willing to GIVE UP to get it? 

Tim Schuster is the Founder of Popup Think Tank. It's what he wants to do most in this life, but there is a lot he isn't willing to sacrifice. By the way, what's your dream?