The Challenge of Doing Hard Challenges

Challenging yourself to difficult tasks and goals is a great way to develop your discipline, and challenge yourself. ShutterStock

This year, I’m doing a series of 40-day discomfort challenges, as a way to continue my training in falling in love with discomfort and uncertainty.

It’s a training I’ve been doing for 1 1/2 decades now, but I’ve been deepening into it even more in the last 5 years. And now I train others in it, in my Fearless Training Program — the uncertainty & discomfort of doing your meaningful work.

This year is going to be a further deepening into that training. I’m going to swim in the deep waters, out of love for life and those who I serve.

I’ll tell you more about my challenges, but first, let’s talk about what hard challenges can do for us.

The Benefits of Hard Challenges

Why do this at all? Someone asked me that on Twitter yesterday: “What are you trying to prove, and who are you trying to prove it to?” I love that question!

With these hard challenges, I’m trying to prove that difficulty, discomfort, uncertainty, resistance and fear are nothing to fear. That we don’t have to run from things because they are hard or scary, or because we feel resistance.

Even further, I’m trying to prove that we can fall in love with discomfort and challenge, bring play and curiosity in the middle of uncertainty and fear, find joy in the middle of chaos and groundlessness.

Who am I trying to prove it to? Myself. And all of you. In service of doing something meaningful in the world.

Imagine that you have some meaningful work you’d like to do — write a book, grow a community, give a voice to others, support those in need, inspire, teach, serve. But with meaningful work comes uncertainty and discomfort, and these can hold us back, because we run from them. Why not just enjoy life and forget about my meaningful work? You can do that, and it would be great, but you can also do your meaningful work, and it can be awesome as well.

In addition to that, hard challenges are incredible! They can:

• Teach us that we can adapt to discomfort
• Show us the beauty of uncertainty and not knowing
• Help us find growth in failure and loss
• Prove that we have the courage to do what we fear
• Give ourselves evidence of our resilience, grit, determination, commitment
• Help us to grow in new and unexpected ways
• Show us what our patterns are when we feel discomfort & uncertainty — if we don’t challenge ourselves to do hard things, it’s almost impossible to see what our patterns are, except of course the avoidance of doing hard things

Each of you has done something hard, maybe many hard things: run a marathon, given birth, raised kids, completed hard projects, dealt with relationship or health difficulties, and much more. These are some of the most meaningful things we can do, and they teach us so much!

Our growth and learning is greatest when the comfort zone ends, and it can also be the most meaningful and joyful parts of our lives as well.

My Year of Hard Challenges

So I’m going to prove all of that with a series of 40-day challenges where I face my own discomfort and fear.

The first challenge, which I started January 1, is jumping into a cold pool everyday with two of my sons. We do some Wim Hof-style breathing before we dive in, then count 3-2-1 and jump into the air! It has shown us that we can do hard things every day, and has been a meaningful bonding experience for us.

I’m still forming the other challenges (vote for what I should do in this quick survey) but here are some others I have in mind, 40 days each:

• Zen sewing (sew a rakusu)
• Write a book in 40 days (in public)
• Record a podcast a day for 40 days
• Meditation retreat in silence
• Learn a language (probably Chamoru)
• Launch something every day for 40 days
• Sleep outside
• Martial arts
• Fasting
• Ego eradicator (hold a difficult pose)
• Eat only lentils & kale
• No Internet except creation & calls
• Public speaking
• Navy SEAL-style physical training

I’m going to pick 8 of these to do after my cold swimming challenge — again, you can help me pick with this quick survey.

I’ll keep a log of how these go, and post about it periodically here on Zen Habits!

The Challenges of Hard Challenges

Of course, we have to acknowledge that these don’t come without a cost. All of the following challenges can be overcome — and I’ll be sharing how to do that — but there are difficulties that we should be aware of:

• We’ll come up with reasons not to do it
• Resistance is real, and can be hard to work with!
• The ego will get in the way — not wanting to look bad in public, for example, or not wanting to not know how to do something
• We can get tired and want to give up after a while
• We can white knuckle it and force our way through it, but not enjoy it
• Completing it can be about the ego as well, wanting to look good is a real danger
• On the other hand, the feeling of not being good enough can also be triggered
• When we get hit in the face by discomfort, we’ll get a strong urge to collapse
• We’ll find a lot of other activity to do instead
• Perfectionism can often come up and get in the way
• Our minds will complain a lot about it!
• We can also get to overwork, exhaustion, overdoing it

These are some of the main challenges. And they are real. And they are wonderful teachers.

An Invitation to You

This year, I invite you to do your own version of hard challenges. That can be whatever it means for you — training for a 5K or half marathon, meditating every day for 5 minutes, learning something, doing the meaningful work you’ve been avoiding.

Do these challenges in small doses — don’t try to overdo it. Give yourself compassion with whatever comes up. Get support, do it with others, and have fun with it.

I invite you also to encourage me along the way — I’ll post to my log regularly, and post updates here on Zen Habits. Follow me on Twitter or Facebook if you’d like to see photos or vids once in awhile.

And if you’d like to train in the uncertainty and discomfort of your meaningful work, join me more than 100 others in the Fearless Training Program!