How to Use Small Wins to Be More Confident

By Jane Mountain | February 23, 2016

be more confident with small wins

So you want to be more confident? Who doesn’t?

But it’s pretty tough to be more confident when your dreams seem totally unreachable and you don’t feel like you’re getting any closer to them, isn’t it?

If you are an adventurer – someone who takes risks in life – you probably ride a roller coaster of confidence. One minute, you’re feeling great, climbing towards your ever-nearing goals and the next…

Confidence freefall! Fuuuuuuuuck.

How do I know this? Because it happens to me. Constantly.

There are nights I wake up in a cold sweat, convinced that none of the things I’ve set out to do will ever happen. In those moments, I am convinced we will end up broke and on the street, without a penny to our names. Like Oliver Twist, we’ll have to learn to pick a pocket or two just to survive.

(Yes, the middle-of-the-night me is a total drama queen!)

I know I’m not alone in this struggle to be more confident, and to be more consistently confident.

Want another way to be more confident? Try our 7-Day Meditation Kick Start →

The Struggle of the Unconventional

One of the great things about travel is that we get to catch up friends who have scattered across the globe in pursuit of their goals. When we chat with adventurous friends about their lives, we hear the same refrain over and over again.

They’re not sure if they’re good enough to ever “make it”.

The demon they all face – and that Stephen and I face with them – is a lack of confidence. Or if not a total lack of confidence, a fluctuation of confidence.

None of us is rich and famous. None of us has a Grammy Award or a Pulitzer Prize. No one is banging down our doors with demands for our talents. Instead, we struggle to book the next gig, we struggle to get more students, or fans, or readers.

In our hearts, we know what our path is. We have created a vision and we are all following through. However, that kind of action is not readily supported by our culture.

The world rewards conformity. To choose an unconventional life is to struggle.

Or, as this article in Men’s Health puts it:

If you’re taking chances in life, here’s an uncomfortable truth: Your confidence will take a hit from time to time, and certainly more than the average person.

One Little Confidence Boost After Another

There is something you can do on a day-to-day basis to help you be more confident. It will help you feel better about your progress, keep you motivated, and keep you on the track to success.

It’s a small change that can have powerful consequences.

To be more confident, you need to start noticing and appreciating daily small wins.

Want another way to be more confident? Try our 7-Day Meditation Kick Start →

In a study, Teresa Amabile, Director of Research at Harvard Business School (fancy!), found that:

Of all the things that can boost emotions, motivation, and perceptions during a workday, the single most important is making progress in meaningful work. And the more frequently people experience that sense of progress, the more likely they are to be creatively productive in the long run.

Think about that.

It’s not a big pay cheque or a customer service award or a promotion that keeps people happy and engaged at work. “The single most important” factor is “making progress in meaningful work”. The level of productivity is connected to the frequency of that sense of progress.

And how can we experience this frequent sense of progress? By tracking small wins.

So you want to be more confident? Who the hell doesn't?  But how can you be more confident when your dreams seem totally unreachable and you aren't getting any closer to them? Click to find out.

So How Do I Use Small Wins to Be More Confident?

It’s simple to put in practice, but can be a powerful way to keep you headed in the right direction and keep you building your confidence.

Every time you experience a small win:

  1. Stop and recognize it. Take a moment to appreciate every little thing that goes well on your journey, whether it’s just sending one important email or making one student smile in yoga class.
  2. Write it down. From today forward, I am going to keep a small wins list – and I challenge you to keep one too.

    Every time you accomplish a tiny step towards your goal, write it down. Every time someone praises you or your work, write it down. Every time you tick another to-do off your list, write it down.

    Soon your list of small wins will be big. Every item on this big list of small wins will be another notch on your confidence bed post. (How’s that for a metaphor?)

  3. Focus on progress, not perfection. Every step is a step forward, even if you trip a little, even if you go in the wrong direction for a while. You can learn and grow from every step, false or true, and isn’t learning and growing exactly what you want out of your adventurous life?

What If I Never Get Any Small Wins?

You do. I know you do. You just have to look for them and start acknowledging them when they come your way.

The thing with people like us – the adventurers, the risk takers, the unconventional – is that we tend to be big thinkers. We have all dreamed a big dream and leapt off the cliff, hoping like hell that our parachutes will open.

It’s this big thinking that can lead to our downfall. Big thinkers tend to ignore the small (good) stuff that happens to us.

Sure, maybe an editor praised your work, or you sold a print of your art. Maybe you just pitched your first story or taught your first yoga class.

As big thinkers, we tend to downplay these little wins. The editor is “not important enough”, the art buyer “doesn’t know anything about art”. Our pitch will “probably be rejected” or that first yoga class “only had two students”.

By focussing on the big, we negate the impact of small wins. They don’t build our confidence, they don’t encourage us, and they don’t help us to move forward.

But with a little effort, we can turn these small wins into daily boosts that motivate us, build our confidence, and increase our productivity.

Got your vision and your action plan?

Small wins are a lot easier to come by if you’ve laid the foundation. For those of you who haven’t been adoringly hanging on our every word for the last two months, let me lay it our for you, step by step.

First, start with creating your vision for your life.

Second, make sure you cast yourself as the hero of your life.

Third, break your vision down into manageable steps that you can work on every single day.

If you only focus on the big picture, you will always feel like a failure (until you win the Nobel Prize. Maybe even if you win the Nobel Prize). But you’ll never win that prize if you quit before you’re even 100th of the way there. Without the confidence to keep moving forward when every sign-post is pointing in the wrong direction and every road is riddled with roadblocks, you’ll never go anywhere.

So start today and see how taking notice of your small wins can give you a big boost in confidence.

Happy adventures, Jane & Stephen


  1. Pingback: Could You Handle Being a Nomad? We Answer Your Travellife Questions! | My Five Acres. Travel. Adventure. Yoga.

  2. Comment by Dermot Barry

    Dermot Barry February 24, 2016 at 2:46 pm

    I try to cram in as many small wins as I can before work. Even if it’s just waking early, doing a little exercise or stretching, getting a short walk in, anything that takes a little effort but enriches me in some way. There is no better feeling than starting a work day knowing that you’ve already achieved a lot! Great idea about writing the wins down!

    • Comment by Jane

      Jane February 25, 2016 at 3:22 am

      Very cool idea Dermot. Starting your day winning sounds brilliant and it’s something I try to do too, even if I often end up starting my day by waking up later than I meant to, skipping my meditation, wasting time on Facebook, and drinking too many cups of tea!

  3. Comment by Diane Wade

    Diane Wade February 24, 2016 at 2:04 pm

    What a great idea! I’m making a “Small Wins” display in my office right now!

    • Comment by Jane

      Jane February 25, 2016 at 3:23 am

      Love it! I keep mine online because I only have a virtual office, but I would definitely have it on the wall if I could.

  4. Comment by Terry Green

    Terry Green February 24, 2016 at 11:24 am

    A win is a win no matter how small it is. We need to stop listening to the people out there who tell us if we aren’t afraid of something it’s not a big enough challenge. Or if it didn’t make us sweat it wasn’t a big win. Sometimes just getting up in the morning and starting over is a big enough win to keep us going. Remember that a lot of small wins are as good as one big win ;)

    • Comment by Jane

      Jane February 25, 2016 at 3:25 am

      Absolutely. The “no pain no gain” mentality is such a force in our culture. Combine that with the “if you don’t have at least 100,000 followers on Instagram you don’t exist” mentality and it’s easy to see why so many people give up on themselves. Thanks for giving me the small win of another great comment on this post Terry!

  5. Comment by Murielle Marie

    Murielle Marie February 24, 2016 at 8:44 am

    I really love the idea of a list of small wins. As a life and business coach I have my clients keep track of them on a monthly basis, because it’s so easy to forget all our little accomplishments, especially when choosing a life of non-conformity (which I know very well too!). I loved reading this post and I wish you all the best in your travels and adventures.

    • Comment by Jane

      Jane February 25, 2016 at 3:27 am

      Thanks so much Murielle. This is a huge mind-shift for me, so I’m glad to hear that I’m not alone and that your clients benefit from it too!

Comments are closed.

Go top