How to Finish What You Start: A Practical Guide to Taking On a 30 Day Challenge

I don’t watch TV.

I meditate before going to bed.

I work out four times a week.

I read 2-3 books a week.

80% of the time, I don’t touch gluten, dairy, sugar, and caffeine, and I can easily go a month without any of those things.

I have a network of systems that keep my digital life secure, organized, and automated.

I sound awful, don’t I?

Don’t you worry, I have more vices and insecurities than I care to admit, but in the past year and a half, I’ve come a long way.


When I set off on this project of random monthly challenges (and yes, I know how random they are), my goal was to find different ways to change my behavior while learning about the things that interested me. I wanted what we all want – to be healthier, more energetic and productive.

I also hoped to build discipline, creativity, and resilience, among other things, so that I could eventually do what I’ve always wanted to do – build something, or, as I’ve been saying for months – write something. Experience and research has taught me that to create something successful, whether it be a business or a YouTube channel or a novel, I need to cultivate this toolbox of qualities.

And I’m doing it. Slowly but surely (more slow that sure), I’m learning all of these things.

30 day challenges

Suffice to say that I’ve become quite good at taking action. I can figure out a way to get from point A to point B pretty quickly, and today I’m going to walk you through the step by step process I rely on for tackling these 30 day challenges.

Below I’ve outlined 10 things that I think about as I head into each new month. Not all of these ideas apply to every single challenge, but they serve as an excellent framework for people looking to take on something new.

1.One thing at a time

When I started brainstorming this blog and all of the things I wanted to attempt, I had four years worth of experiments written down. That scared me. 

But when I focused solely on the challenge in front of me, everything changed. 

You have to focus on just one thing. Even better if it’s small. Like if you want to floss on a regular basis, just floss one tooth type of small. It sounds stupid, but it works because your willpower isn’t pulled in twelve different directions.

You’re a hair outside of your comfort zone with enough energy and willpower to get you through the change, which is exactly where you need to be to succeed.

2. Decide why you want it

Be honest about your motivations because change of any kind is impossible without self awareness.

A health issue is a great motivator because when health fails, you can’t deny reality any longer. You have to face the fact that change needs to happen.

But not every change has to stem from a wakeup call. Here are some examples of my own why’s:

the why

3. Make the commitment and make it specific

All short term goals should be specific, time bound, and written down (it helps formalize the commitment).

Write down exactly what you are going to do (zumba class at 24 hour fitness), for how long (on Mondays and Thursdays for the month of August), and hang it up somewhere you can see and be reminded of it every day.

4. Make it public

I’m lucky in that I have this blog to keep me accountable. Public commitment makes it harder to slack off, so share your goal on Facebook, talk about it with supportive friends or even with an online community like or StickK.

5. Work Backwards

Specific goals work because they allow you to break the challenge down into bite sized chunks. I call it “reverse engineering”, where I ask:

  • What books do I need to read?
  • What tools or equipment do to I need to use?
  • What steps do I need to take?
  • What skills do I need to learn?
  • What’s going to make or break this challenge?

For example, for the 15 minute plank challenge, I started with a baseline plank time (6 minutes) and then determined that I needed to:

  1. Work with my trainer to physically prepare my arms, shoulders and core
  2. Study the mental preparation of endurance athletes
  3. Show up every day to train

15 Minute Plank Training Program

6. Get Help & Support

I rarely have a challenge that I take on entirely on my own. I need to rely on people, books and resources that can help in areas where my skills are lacking. I’ve hired teachers, purchased online courses, hired freelancers on and, borrowed stuff from friends, asked for their help and combed YouTube for any hidden tips and tricks.

I also turn to people I trust and respect who can provide me with support and encouragement when things get difficult.

7. Design your environment

This one is particularly important if you’re taking on a challenge that requires a healthy dose of willpower (i.e. diet and nutrition). Visual cues, inspirational quotes, blocking off time on your calendar, and hacking your space are all excellent tools for make quitting more difficult.

Here are some more examples of environmental hacks I turned to:

  • Food challenge: rid my house of all gluten, dairy, sugar and general junk food items; stocked my pantry with an abundance of healthy options 
  • Sleep challenge: unplugged all lights to sleep in complete darkness, slept in cooler temperatures, removed devices from the bedroom
  • Short story challenge: blocked off time each morning to write; printed out a fake book cover to place next to me whenever I wrote to keep the inspiration alive

Screen Shot 2015-02-26 at 11.21.47 AM

8. Anticipate roadblocks and decide how to overcome them

Think about potential situations or circumstances that might cause you to make a bad decision, and then decide how you’re going to deal with them. 

When I went on my elimination diet, I declined many social invitations because I knew I didn’t have the willpower to say no to bread or wine or dessert. I also made detailed daily menus so I knew in advance what I was going to eat for breakfast, lunch, dinner and snack.

When I felt lazy to write, I set five minutes on a timer and gave myself permission to quit working after those five minutes. Most of the time, I kept going.

9. Finished is better than perfect

This is a motto I live by specifically for any creative challenge, like this current YouTube project (you can watch a video here!).

As much as I’d like to fine tune every single detail to perfection, I have to be selective about where I invest my energy. I have a long list of to do’s (planning, shooting, editing, graphics, promoting, music, special effects) to complete in a short amount of time. While it’s tempting to edit and tweak each video, logo, intro jingle and channel art 137 different times, I don’t. It’s not realistic.

Instead, I get to a place where the work is finished, but by no means perfect.


10. Just because you screw up doesn’t mean you should quit

Just because you fail doesn’t make you a failure. It happens to the best of us. If you do mess up, don’t internalize the setback by telling yourself that you’re a loser who’s not capable enough or smart enough. Learn from the mistake. Figure out what triggered the lapse and find a way to deal with it next time.


A few final thoughts on creating habits that stick

So many people underestimate how much they can accomplish in a short amount of time. It’s actually quite easy to give up alcohol or sugar, meditate, or create a YouTube show in 30 days. It’s a short enough time frame where you can see the light at the end of the tunnel and hustle your way through it.

The hard part is sustaining the habit it over time.

It’s so easy to fall back into old ways. That’s why it often takes months, even years to make a habit really stick, to the point where the behavior becomes effortless.

I struggle with this every day.

I still chow down on pizza and birthday cake. Not often, but it happens.

I haven’t sewn a stitch or played the guitar or taken a cold shower in months.

I’ll go weeks without meditating only to have to fight my way back to a regular practice.

Even though I spent all of January clearing out the clutter from my house, I’ve allowed the “stuff” to accumulate… and then some.

And worst of all, I don’t write every day.


But I do know how to focus when I need to sit down and do the work. I have the discipline to write or sew or practice when the challenge calls for it. And I have the mindset to take on uncomfortable and even painful things because I’ve done hard things before.

That’s why I’m such a believer in the power of the 30 day challenge as a way to jumpstart the process of change. I believe in small wins because progress builds confidence, confidence drives motivation, and motivation inspires action.

It ultimately teaches us that we have more influence over our behavior than we give ourselves credit for.

And that makes all the difference.

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