Why I Stopped Setting Goals and Started Challenging Myself

Updated September 2026 with a simple framework for pairing daily challenges with real goals, plus answers to common questions.

Have you ever set a goal? Probably.

How about a New Year’s Resolution?

I have set goals and resolutions many times, and guess what? I never meet my goal and I never feel resolved!

This year I decided to do something different. I decided to challenge myself. You should challenge yourself too! But why?

Goals: the object of a person’s ambition or effort; an aim or desired result.
synonyms: objective, aim, end, target, design, intention, intent, plan, purpose

Challenge: a call to take part in a contest or competition, especially a duel.
synonyms: dare, provocation

Goals sound lofty–they seem distant and not something I can do today. Challenges sound more competitive and daring and I love the word “dare”.

So here are a few of the things I’m challenging myself with.

Health

1. Eat more whole grains daily.
2. Eat more greens daily.
3. Floss and mouthwash daily.
4. Don’t drink soda.
5. Workout 3 times a week.

Challenges instead of goals. Challenges are things to beat daily.

Hustle

1. Blog weekly.
2. Avidly read about copywriting, content marketing, and blogging.
3. Grow and engage my Twitter following.
4. Replace my iPhone/Facebook with my Kindle when I’m bored or have down time. Read 5 pages of a book everyday.

Practical Application

Right now, sit down and jot down 5 things you want to do EVERYDAY. Start with something small like flossing. I found that was the easiest place to start. Now start doing it! The first step to winning your challenge is by doing it everyday.

Want some accountability on your challenges? Hit me up on Twitter, I’d love to be your challenge partner.

What are some things you’re working on? What do you think about challenges instead of goals?

What I’d tell you today

I still love the word “dare.” Daily challenges work because they’re small enough to do today, and you can see whether you did them or not.

But if I were writing this post today, I’d add one thing. It isn’t really challenges instead of goals. It’s challenges that serve a goal. The goal is the direction. The challenge is the daily step that gets you there. Without a direction, you can floss faithfully for a year and still feel stuck on the thing you actually care about. Without a daily step, the goal just sits on a sticky note.

A simple framework: Direction, Daily, Check-in

Here’s a simple way to put the two together. You can do it in fifteen minutes.

1. Pick a direction. Choose one area of life and write down where you want to be in 90 days. Make it specific and measurable. “Get healthier” is a wish. “Walk 30 minutes without stopping by June” is a direction.
2. Turn it into a daily (or weekly) challenge. Ask, “What’s the smallest thing I can do today that moves me that way?” Then shrink it again.
3. Schedule it. Put it on your calendar at a real time. What gets scheduled gets done.
4. Track it. A check mark on a paper calendar works just as well as an app. Seeing the streak is half the fun.
5. Check in weekly. Take ten minutes at the end of the week. What worked? What didn’t? What will you change next week?

Let’s walk one example all the way through. Say you borrow “Workout 3 times a week” from my list above.

• Direction: In 90 days, you want to walk or jog for 30 minutes without stopping.
• Challenge: Walk for 20 minutes on Monday, Wednesday, and Friday.
• Schedule: 6:30 a.m. on those three days, shoes by the door the night before.
• Track: A check mark on the calendar on the fridge.
• Check-in: Every Friday, add a few minutes or a short jog if this week felt easy.

See the difference? The challenge is still small enough to do today, but now it’s pointed somewhere.

Start with fewer challenges than you think

In the original post I suggested writing down five things to do every day. If five feels like a lot, start with one to three. You can always add more once the first ones feel automatic.

And when you miss a day (you will), give yourself some grace. One missed day doesn’t erase the streak you built. Just don’t let one missed day turn into a missed month. Get back to it tomorrow.

One more update: Twitter is now called X. If you want an accountability partner, the best way to keep up with me these days is my email list.

You don’t have to overhaul your whole life this week. Pick one direction, one small dare, and do it today. Then do it again tomorrow.

Frequently asked questions