Ashley Kelly

How to acquire confidence and become a better version of yourself.

Ashley Kelly

Sometimes, it can feel like everything around us has been constructed to make us feel not good enough. With every swipe and scroll comes another reminder of how we’re not successful enough, not hot enough, not smart enough, not rich enough, not cool enough, not whatever enough.

It’s easy to start drowning in the comparison game and start beating ourselves up.

I do think there is such a thing as a healthy dose of discomfort, but going too far down this path is just painful, not useful and definitely not conducive to building confidence.

I recently read The Magic of Thinking Big by David Schwartz and he stated in his book that:

All confidence is acquired, developed. No one is born with confidence.

This got me thinking.

So, what exactly is confidence?

The dictionary defines it as a feeling of self-assurance arising from an appreciation of one’s own abilities or qualities.

To me, this means to trust.

To trust yourself.

And in order to build trust whether, with yourself or with others, the key is action.

Action is how you acquire confidence and action is how you develop it.

"To think confidently, act confidently. Motions are the precursor to emotions." Dr. George Crane - Applied Psychology

I started thinking about the people in my life who radiate with true confidence. How do they behave? What do they do consistently?

And, I started reflecting on times in my life when I’ve radiated with confidence and the times in my life when I haven’t.

What was I doing during those times? How was I behaving during those times?

One particular story kept coming up in my thoughts.

I remember being nine years old. Our family moved to a new town and I was about to start 5th grade at a new school.

I was scared. I was dreading it.

I was sad to leave my old friends and have to embark on this journey of making new ones.

I remember telling myself on my first day of school that going home friendless was NOT an option. At recess, I was going to talk to everyone I could, share my snacks, invite myself to play games and be my silly self.

And that’s exactly what I did. I crushed it.

I made lots of new friends (some I still have today).

I also made a significant change to my beliefs that day. I believed that making new friends and meeting new people was fun and I’ve kept that belief with me throughout my life.  

Nine year old me trusted herself (at least on that day) and she took action even though she was terrified. It was a profound confidence building moment in my life. 

When I need to draw upon some inner self-confidence, I often think about that girl. She had that confidence in her then, which means, I still have it in me now.

We overthink confidence sometimes as this magical thing outside of ourselves. But it’s not really. It comes from within us and is developed by the actions we choose to take.

During my reflections, there were a few recurring themes. I’ve summarized them below into practical steps and ideas to help you acquire and develop your own confidence. 

Here they are:

1. Show up and stand up straight

My mom used to nag at me when I was growing up…

Don’t slouch” as she grabbed my shoulders and pulled them back while I was sitting at the breakfast table.

She’d ask me...“are you really going out like that?” As I scrambled out the door in my dirty track pants and bedhead.

I used to think, ugh mom what is your problem, as I rolled my eyes at her (to be fair to myself, I was a student at the time).

Turns out my mom had a point and there’s an actual theory behind this called embodied cognition. The concept is that not only do our minds influence our bodies, but our bodies also influence our minds.

You know, when you look good you feel good and when you feel good you look good.

Or how about when you smile you feel happier and you’re happier because you smile.

Sometimes, it can feel hard to change our thoughts. But, it's not that hard to change our posture, smile and make ourselves look a little nicer. 

So, clean up and put your good clothes on.  

Do your hair.

Don’t look like Gollum...seriously.

You can always start here. 

2. Make eye contact and smile at other humans

Okay, I don’t mean walking around with a perma-smile and staring at everyone all the time because that would be weird.

But I do mean when you catch someone’s eye on the train or walking down the street, the person at the store, your coworker, client, friend or whoever you’re interacting with, make eye contact.

In The Four Hour Work Week by Tim Ferris, he talks about a concept he learned called eye gazing where you practice maintaining eye contact with people until they break it. The idea is to purposely make yourself uncomfortable with the goal of overcoming that discomfort.

I used to have a long commute to work and I thought it would be fun to try this. It definitely felt strange at first. I’d practice on the train and then in the office and with anyone I was interacting with.

I’ve found this to be a great exercise in building my own confidence and leading interactions with people.

And along with eye contact, smiling helps too, even if the other person doesn’t smile back.

I notice in my own life when I make the effort to smile, I see more people smiling at me.

It keeps momentum positive and, it feels good.  

You’d be surprised how much of an impact this can have on your confidence and life.

3. Move. Your. Body.

Even just a little bit, like for 5 minutes (because you’ll be inclined to keep going - the hardest part is starting).

Get your blood and endorphins flowing.

Do something good for yourself and remind yourself that you care enough to take care of the only body you get in this life.

And if you already exercise, try doing one more rep or go for one more minute than you normally would.


Just a little further.

Revel in the accomplishment.

Even if it’s tiny.

4. Compliment someone and consciously look for the positive

Tell a coworker that you really like the way they did something or tell your significant other something you appreciate about them.

Positivity has a ripple effect and it gets your mind thinking on a positive wavelength; looking for the good in others, in situations and in yourself.

It can also influence the recipient of your positive words to do the same. 

It’s easy to complain, especially when others around you are doing it. Complaints seem to roll off our tongues unconsciously about the weather, the traffic, our coworkers, our friends, our partners.

Looking for the good requires us to consciously shift our minds in a new direction. People want to be around those that make them feel good. 

When you catch yourself complaining and spiraling down in negativity, try countering your statements with the positive side. Say it out loud. Give your compliment to someone. 

Don’t add to the downers. We’ve got lots of those.

Be someone that lifts people up.

5. Take risks and have an open mind to failure...even if you’re scared

Seems counter-intuitive, I know. 

What if I fail?

Yeah, that’s exactly the point.

You might.

It might epically suck.

But you’ll find with an open mind, you will have learned something and you’re a little stronger than you were before.

This is where you start to discover what trusting yourself is all about.

I teach English online.

I have this one particular student, we’ll call him Tim, who I absolutely adore. Not just because he’s actually adorable, but because he never fails to inspire me.

He shows up every day with a contagiously positive attitude and a big smile.

He tries to spell and sound out new words. When he gets it wrong, he tries again. He doesn't let the fear of embarrassment stop him. And he has the best time doing it.

Laughing at himself, cracking jokes.

Every day, I’m like damn.

This kid!

He’s 6 and he’s my role model.

It’s not always about succeeding.

It’s about trusting yourself to try in the first place.

6. Get to know yourself a little more each day

Who even are you?

If confidence is trusting yourself, how can you have it if you don’t know yourself?

'Yourself' is a work in progress and always will be.

Dig deeper and do some self-assessment. Question your assumptions, biases, beliefs, opinions.

Reflect on what kind of person you were today.

Ask yourself who you are becoming?

Look inward, not outward. The more you learn about who you are, the more you can act with integrity and stay true to yourself.

I'm currently reading Ego is the Enemy by Ryan Holiday and this quote really resonated with me. 

“We can’t improve the world if we don’t understand it or ourselves. We can’t take or receive feedback if we are incapable of or uninterested in hearing from outside sources. We can’t recognize opportunities - or create them - if instead of seeing what is in front of us, we live inside our own fantasy. Without an accurate accounting of our own abilities compared to others, what we have is not confidence, but delusion. How are we supposed to reach, motivate, or lead other people if we can’t relate to their needs - because we’ve lost touch with our own?

7. Accomplish tiny goals and do what you say you will

Small things and tiny steps are my favourite.

They build momentum and lead you to bigger things.

They are the foundation of building trust and developing confidence within yourself.

If you said you were going to do something today, like go for a run, bring something to work for a coworker, be on time, start your project or whatever it is…


If you’ve fallen off the wagon, like I have many times, there’s no better day than today to get back on.

It's not always about the big things or the great things we do once.

Building confidence and trust happens in the mundanities of consistency in the small things. 

With each consistent action and tiny accomplishment, you build one more ounce of trust in yourself

Why I decided to quit my job and travel.

Ashley Kelly

I had a good job at a growing tech company.

I was making good money.

I had a fantastic partner (I’m still with that partner btw, just for the record).


A fun social life.

I finally got offered the promotion I was waiting for.

And then…

Not only did I turn it down…

I quit.

I know, the epic eat dirt story where I flipped off my boss would be cooler.

But it wasn’t like that.

Things were fine. Better than fine, good really.

I enjoyed the bubble of my comfort. It was pretty cushy.

I liked my job. I liked my life.

So, why would I leave that? Especially when things were good?

When my partner and I got together a couple of years ago, one of our first conversations was about how we both wanted to travel, live in different cities and explore different ways of living.

We were both on the same page.

We agreed one day, we’d leave home and our jobs and go do exactly that.

So when I finally got the promotion I was waiting for (and really wanted btw) the conversation about our lives and what we wanted the next chapter to look like came up.

You know, that question…

If not now, when?

Yeah, that.

I knew that if I said yes to the promotion, that would mean at least another year, most likely more, that I’d be putting in at the company.

Because, when I say yes to something, I go all in.

Don’t get me wrong, part of me really wanted to say yes. Part of me wanted to push off my dreams to someday.

And there it was.

The trap of the proverbial golden handcuffs stood before me welcoming me in with all the luxuries that comfort can buy.

It was tempting.

But the little voice in my head was saying:

And then one year becomes two, two becomes five, five becomes ten.

And before you know it, it’s 30 years later and I’m telling my kids that I wish I travelled and explored life when I was young.

As much as I wanted to say yes to the promotion, it would have been safe. It would have been comfortable.

And if I said yes, I wouldn’t have been saying yes to just a promotion.

I would have been saying yes to mediocrity.

And that’s why we ‘quit’ (my partner and I worked for the same company…so we both quit).

“Mediocrity doesn’t always mean underperforming — it’s a sliding scale and a state of mind. It means settling in and succumbing to stasis. Mediocrity comes from the Latin words medius, meaning middle, and ocris, meaning rugged mountain. Literally translated, it means to settle halfway to the summit of a difficult mountain. It’s a compromise of abilities and potential; a negotiation between the drive to excel and the biological urge to settle for the most comfortable option.” Die Empty, Todd Henry.

That’s what we were saying no to. That’s what we were leaving.

It’s easy not to push yourself. It’s easy to stay complacent.

It’s not so easy to shake up your comfort in exchange for continued growth. To choose to keep climbing to the summit knowing you’ll face uncertainty with each step.

That’s the path we decided to take when we quit.

We left good behind so we could fulfil a dream.

And now, we’re living that dream.

Isn’t that the great escape?

This post was originally published on Medium

How your procrastination might be helping you.

Ashley Kelly

You’re sitting at your desk ready.

You’ve told yourself that you’re going to do stuff now - write, design, make, paint, fix your resume, work on a project.

You’ve got your tea, your colored markers, your notebook, a scented candle lit and you’re all set.

It’s go time!

And then, the deterring happens.

You stare emptily at the computer screen.

Sip your tea.


See if your markers work (hmmmm, that’s a nice color you think to yourself).

You grab a blanket because you’re kinda cold.

Ok, ready.

Sip tea again.


Look for a snack because, maybe you’re hungry. Except you’re not really...but just in case.

Ok, for real.

Now you’re ready.

You start Googling “how to _____.”

Oh, that looks interesting. You start reading “477 ways to ____.” You see another article that’s obviously super important “738 ways to not ____.”

You think to yourself, holy, I totally need to be doing that. Why am I not doing that? Ugh.

Make a note that you’ll never read again.

Ok, now you’re starting to feel a little discouraged.

You make your way over to the never-land of social media.

You start scrolling hoping to stumble on the magic thing that’s going to propel you to start.

You read inspirational "be amazing." (eye roll)

You scroll through memes, watch cute dog videos and look at random pictures of people you don’t even know.

You lose track of the time.

It’s 5 hours later.

Chip crumbs have invaded your shirt.

Netflix is seeming tempting...oh so tempting.

You close your laptop.

Accomplishment on the project you set out to do = 0.000.

To be continued...

I hate admitting it, but I’ve definitely had more than one of these nights.

Sometimes, it’s the resistance, simple as that. And you have to buckle down and just do the work.

Other times, I think we either haven’t broken the thing down into small enough pieces or perhaps, it’s not really that important to us. So we stall.

But, what if sometimes that procrastination is something else.  

What if it’s instinct trying to come through.

But because we’re so quick to accept external pressures, we dismiss it and simply chalk it up to us being lazy procrastinators.

For me personally, if I want something, I’ll go get it. I’ll do it. Get that job, start the project, whatever it is.

So if my procrastination is lasting longer than it should be, I know now that my inner wisdom is like “yo ashley, I need you to take a deeper look at this.”

What if your procrastination is nudging you to dig and ask different questions.

Maybe questions that might reveal that you don’t really want to move down this path or you have other desires that haven’t made themselves clear yet.

Or maybe, it’s just wrong timing and hesitation is the only way your ‘inner wisdom’ knows how to communicate that to you.

If you’re stuck in a procrastination rut, stop asking yourself what’s wrong with you.

That question won’t produce a good answer.

Ask yourself if your thing is important to you, really important to you, and why?

If that’s a yes, have you broken your project down into small enough pieces?

If that's a yes, chances are it's a matter of pushing through that resistance.

But if there's any hint of a 'no' or an 'I'm not sure' in there, explore it. 

Ask yourself what's really going on here?

What are you really waiting for? 

Before you write-off procrastination completely, give it a chance.

Poke it a little bit and see where it takes you.

It might actually be trying to help.  


What are you putting into your upgrade?

Ashley Kelly

In the past, I’ve made resolutions and set goals at the beginning of a new year. I’d write them down and then leave them in my journal.

I didn’t measure or look at them after that until the year was over.

The year would fly by and at the end, I’d reflect on the things I did and accomplished. I only reviewed the bigger things since the smaller wins and losses got lost in the everyday minutiae.

Some things stuck and I achieved things I’m proud of like:

- Writing daily
- Making a career change
- Ending a relationship
- Starting a new relationship
- Making more money
- Saving enough money to travel for a year

Funny enough, I seemed to pleasantly surprise myself with some of my accomplishments. Has that ever happened to you? You look back and realize that you achieved something you had written down but totally forgot about? 

I’m not saying that writing goals down once at the beginning of the year and never looking at them again is the most effective strategy (actually, it's probably the worst lol), however, there’s something powerful in the simple act of writing it down, I must admit.

For me though, I always felt like my accomplishments were never enough. Like, something was missing.

I’d end the year feeling like I should have accomplished more. Like my life should be fuller.

But then, I’d do the same thing again next year.

While I have been able to reach goals I’ve set, I felt like I was living to cross tasks off my daily to-do list. Living pointlessly efficient and efficiently pointless.

Looking back, I believe that the feeling of disappointment comes from not fully understanding or clearly defining what a meaningful accomplishment is. And, not celebrating and appreciating the smaller wins and losses that take place in our lives often enough.

This got me thinking.

The tools we use have scheduled updates for upgrades to ensure the next version is better than the last. You know, Version 1.0 becomes Version 2.0 and so on.

Sometimes, the next version isn’t that much better, the upgrades were almost unnoticeable, or maybe, the upgrade triggered another bug that needs fixing.

And sometimes, the next version turns out epic.

At the end of the day, an upgrade happened. A change took place - for better, or for worse.

As humans, I think scheduling our own updates can help us ensure that the next version of ourselves is being upgraded with the ‘right stuff’ to keep us on track to living a meaningful life.

As our lives happen, our values might change, our beliefs might shift, and what we once wanted we may no longer.

How can we be sure that we’re moving in the right direction if we don’t take the time to check in with ourselves and update?  

This year, I decided to schedule two major updates. One on my 31st birthday (Version 31.0) and then the next 6 months later (Version 31.5).

I decided that I would set value-themed goals and then intentionally choose actions that are aligned with those goals instead of just setting outcome goals. At the 6 month mark, I would review my progress and update my values and goals if necessary.

I said that for me, 2018 would be a year of:

- Pushing out of my comfort zone - so that I can expand and grow beyond my own bubble
- Learning new things - so I have more in my toolbox to draw upon
- Writing and reading more - so that I can keep continuously improving
- Doing things that scare me - so that I can learn to be more comfortable in my vulnerability
- Deeper self-reflection and personal development - because I spend 24/7/365 with myself so, getting to know myself better can’t hurt, right?  

These seem vague, I know, but I prefer it because it leaves room for adjustment. These are meant to be guides.

And any outcome goals I make need to fall within one of the above categories. 

Over the last six months, Version 31.0 of myself has:

- Quit my full-time job
- Began a year journey of world travel with my partner
- Reduced all my belongings into one bag. For real, all my stuff fits in one bag. Because do I really need that?
- Started learning Spanish
- Have read 20 books and counting
- Began exercising more regularly again
- Officially published my writing online which has always been something I’ve wanted to do
- Started teaching online

I have accomplished more in the last six months than I have in any other six month period of my life while moving the direction of my life toward things like risk, discomfort, vulnerability, exploration, creativity, and reflection.  

I recently read a fantastic book, Die Empty by Todd Henry. He summed up why this concept is so important:

“Even small amounts of success can be the harbinger of complacency - or worse, paralysis - because every milestone you reach ushers in new uncertainty. Where to now? What are the next logical steps? Does this work still matter, or is it time to change course? Because we are biologically hardwired to form habits around rewarding activity, when we accomplish a goal or taste the sweet fruit of success it’s tempting to keep pushing the same levers over and over again. However, this approach is often a fast track to mediocrity. The key to long-term success is a willingness to disrupt your own comfort for the sake of continued growth.”

Although our hardware gets older each year, our software can continue to get better, wiser, and stronger if we keep upgrading deliberately and push ourselves out of the confines of our comfort.

What are you putting into your upgrade to ensure that your next version is going to be even better than the last?

What journey are you on? 

What is a meaningful accomplishment for you?

Whatever that might be today might be something different in the future.

Keep checking in with yourself.

Schedule your updates.

And, never stop upgrading.

Write a letter, gain some clarity...and a tip for finding your writing voice.

Ashley Kelly

I started journaling back in 2012 because I wanted to get to know myself better and understand my emotions. 

When I look through my journals, some of the things I’ve written make me cringe when I read them back.

I literally think, ew.

And some things are insightful, funny, deep, and I think, wow you awesome human, you.

In my experience, I’ve found the best way to gain clarity about something is to write it out. Maybe it’s an emotion, an idea, or something you want to say to someone.

For me, I've found writing a letter to the thing really helpful - especially if I'm stumped in the moment and don't know where to start. There's something about writing the words "Dear (thing)" that opens a door in my head and enables me to start writing.  

I think it has something to do with writing to it and not about it that allows the words to flow. 

I've written letters to myself, to my emotions, to my ideas, to people, to my dog, to strangers, to the universe, and random things.

I try to be specific and focus on one thing at a time.

One idea.

One expression of gratitude.

One emotion, one person or thing.

Sometimes brain dumping is necessary, but for the most part, I like to stick to this premise because it keeps things concentrated.

It allows you to deal with one issue at hand.

It also allows you to see if there are patterns.

Maybe one thing keeps coming up over and over.

Maybe, you need to dig deeper?

Seek closure?


Let go?

Say goodbye?

This method of journal writing opened my eyes to what kind of relationship I had with anger, sadness, love, patience, my partner at the time, to name a few. 

I’ve also found that this has helped me become a better verbal communicator.

I consider myself gregarious and extroverted, but I’m also a private person so I find talking through my feelings difficult at times.

When we talk, I find that we limit what we say sometimes for various reasons; to protect ourselves, to protect the other person, to limit our vulnerability, to avoid the truth.

Sometimes, we can’t get it out because we’re overwhelmed with emotion.

But I find with writing it down, you can be real and get it all out.

Obviously, you can't be like, "oh hold on one sec while I write out my thoughts first" before every interaction. It's simply not possible and would just be weird. 

But taking some time to reflect and write helps to clear your head, solidify ideas, and work out things you’d like to say out loud.

Writing has helped me work through difficult decisions in my life and career more than anything else.

It also serves me as a well of insight and inspiration to write more stuff, communicate better, and be an overall better human.

Which brings me to this “writing voice” everyone talks about.

Being a writer has always been something I wanted to do.

When I began thinking about publishing my work and taking my writing to the next level, I could feel myself resisting. My mind was racing with all the things I needed to do in order to become a writer. One of those things was, finding my writing voice.

But after some thought, I was like, wait a minute.

I write stuff.

I’ve been doing it for years.

I already am a writer.

My writing voice is the voice I already have.

It’s me.

How I talk.

How I would speak to a friend.

And my writing voice will continue to develop and evolve as I continue to develop and evolve as a human.

So the voice will change as I change.

And for me, that works.

If you’re struggling to find your writing voice, try reading through your journal entries. You might pleasantly surprise yourself with the writing voice you already have.

If you don’t have journal entries to flip through, start writing one now.

Don’t filter it, just write.

Try writing a letter to someone or something if you don't know where to start.

It can be just for you and your journal if you like. Maybe you send it to someone, or not.

Maybe you burn it.

Or, maybe you create an epic piece of content to share with the world.

It’s also pretty fun, just sayin’.

You could try starting with one of these:

Dear (insert family member/friend/lover’s name here)...

Dear Max (That’s my dog. Love letters only please)...

Dear stress…

Dear fear...

Dear time...

Dear cute guy/girl on the train...

Dear guilt...

Dear inspiration...

Dear rejection...

Dear business idea that won’t leave me alone...

Dear ego...

Dear Dumbledore (kidding...but not)...

Dear 16 year old me...

Dear 100 year old me...

Happy writing.