Monday morning I sat down and took out my trusty bullet journal. I was planning to write a post on investing followed by another post on student loans. I was ready to tackle that to-do list.

But when I opened the journal I accidentally flipped to a page near the beginning and found a journal entry that I’d written back in June 2017.

As I stared at the words I didn’t even recognize the person writing them. I started reading and began to remember the moment I wrote them. I wrote it while flying to California (from London) and should have been elated to spend 2 weeks visiting friends and family.

I wasn’t.

This journal entry was written by someone confused and frustrated by their direction. At the time I didn’t know what I wanted to do, what I was good at, and I was feeling profoundly unconfident. I had picked up journaling as a semi-regular habit to try and help me move past these feelings (I even wrote a post about how I had been feeling like a fraud and dealing with imposter syndrome).

Looking at that journal entry and feeling completely disconnected from the person I was then has made me reflect on how I’ve learned to become so much more confident. There wasn’t one singular even that increased my confidence or a secret “trick” that instantly worked, but there were a few conscious changes I made that created a big shift. Changes that I think we can all use to boost our confidence.  

Before this, I had always considered myself a reasonably confident person. In fact, that’s probably one of the things Jordan would say he liked most about me when we first met.

But a few years ago after we moved to London I ended up on a different path that I thought I would. I’d always worked for prestigious companies and I’d gotten my MBA from Duke, one of the best schools in the country.

Being in a country that no longer valued my degree or my work experience was surprising. Navigating a new path shook me. I could no longer say, “I am a (insert job title) for (insert big name company here)” and a part of my identity was gone. I don’t know if I realized how much it really affected my confidence.

As I ventured out on a less traditional career path, my struggles with confidence were magnified. Pitching and getting a lot of “no’s” is difficult. Setting the right price for your work when you’re nervous that you’re not the absolute best at your job is nearly impossible. And continuing to write and share your knowledge (and your flaws) can have you worried that people are judging you.

It was easy to see just how my waning confidence was not only going to hold me back from bigger things in life, but it was also going to affect my bank account.

While I don’t relate to that person who wrote that entry back in June 2017, I’m thankful to have that journal entry as a constant reminder as to how far I’ve come.

What I’ve changed:

The funny thing is that I didn’t set out to specifically boost my confidence. In all honesty, I don’t know if I would’ve considered myself unconfident at the time. So if I didn’t even realize what was wrong, how did I set out to change it?

I spent the last few days reflecting on the changes I’ve made since June, to really understand what has helped me to become more confident and identify less and less with the person who wrote that journal entry, in hopes that some of my changes can be useful to you.

There are three ways that I’ve made changes that have helped me to get to this place.



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1.Changing the internal talk track

We all have one of these. It’s that little voice that pops up all day long. And whether that voice pops up in a supportive fashion or with more degrading comments affects how you feel.

As someone who skews to the more extroverted end, working alone from home is challenging. When I’m alone I tend to ruminate, going over and over certain situations or actions I’ve taken, which invariably ends with me playing a completely negative talk track in my head.

I’ll think things like:

“I’m so far out of my comfort zone here. They regret hiring me already.”

“This article is so poorly written. Why am I even trying to pretend that I can write?”

“Why can’t I ever get through my to-do list? I’m so lazy.”

The things that can run through my head are so mean! I used to fixate on these thoughts and literally rob my days of joy.

I remember Jordan coming home one evening and I couldn’t stop talking about how I was over the moon elated about a pitch of mine being accepted. Five minutes later a different pitch I had written was rejected and the internal talk track popped up with, “what makes you think that people are actually going to want to publish what you write?

I’ve noticed over the past few months that rather than trying to ignore that negative talk track, I find myself challenging things.

If I find myself thinking:

“Why would anyone listen to me?”

I’ll flip it around and say:

“Why wouldn’t they listen to me?” (said with a sassy shoulder shrug, naturally).

If I find myself thinking:

“I’m never going to make enough money to have this whole self-employment thing work out.”

I try to change it to:

“I’m so lucky I have the ability to make as much money as I need to.”

While it doesn’t always instantly change things, I have noticed that on the whole, my internal talk track has been much more positive. The things I used to say to myself are no longer part of that internal dialogue and are no longer taking a heavy toll on my confidence.

2. Identify overthinking

I don’t usually identify as someone who is indecisive. But when my confidence was low I was continually second guessing everything. I couldn’t make a decision without questioning it the very next day. I’d often find myself avoiding making decisions by asking overwhelming questions (with no quick and easy answer).

If I was stuck trying to make any sort of career decision, I’d find myself asking, “what do I want to do with my life?” That big question threw me into an indecisive tailspin because, how do you even answer that?

I didn’t even realize how often I was asking that question until Jordan had to not-so-gently point out that he was tired of me responding with that question when all he had done was ask me how my work day went.

(To be clear, I’d also throw myself down dramatically on the couch in frustration while asking, “what am I going to do with my life?” It was fair for him to suggest I get a new response.)

I realized that a lot of my indecisiveness was stemming from emotional responses getting in the way of what should be rational decisions.

Rather than getting stuck on a problem and working it out rationally, I’d find myself spiraling down an emotional drain overthinking everything. Rather than taking action, this spiraling would leave me stuck. Then cue the internal talk track about being lazy and not getting enough done. What a cycle.

To figure out if I was overthinking and being indecisive because of an emotional response or a rational reason, I began asking myself “why?” As in, “why am I asking this?”, “why is this taking so long”, or “why am I struggling to make this decision?” 

Simply asking “why?” and getting to the root of the problem, helped me to break my chain of indecisiveness.

3. Simplify

After being thoroughly exhausted by 2017, I knew I wanted to make life easier in 2018. (side note: I’m sure in a few months I’ll laugh about how I’m aiming to make life easier with a baby on the way. I’ve heard babies do not make things simple.)

I spent much of December being thoughtful about my 2018 goals and how I wanted to live my day to day life. The overwhelm and exhaustion that was eroding my confidence earlier in the year was in part caused by too much stuff. Too much mental stuff, too much disorganization, too many ways for me to be indecisive.

Rather than going home for the holidays, Jordan and I spent our time decluttering everything: our closets, our goals, and our money.

I shared this last week, but decluttering all of our accounts in 2017 made such a huge difference in my confidence in decision making. While Jordan was always organized, I had to pull myself together in this area. Using Personal Capital* and the method that I break down in this post was truly a game changer for simplifying money.

Going through this exercise and taking time to simplify our life was an unexpected boost for my confidence. I see things more clearly, I’m more focused on what I want, and I know I have the tools at my fingertips to help me determine how to get there. Life is less messy – for now.

The results I’ve seen

The fact that I didn’t even recognize the person who wrote that journal entry in June, is the biggest result I could have asked for.

Aside from this, I have realized my general ability to get more stuff done. While I’m still a procrastinator (old habits die hard), I’m not indecisive. I’m not asking myself what to do next and taking months to figure out my direction. I now have a mile long to-do list full of things I’m excited and ready to do.

I’ve started making smarter decisions for my money as well. Rather than pricing my services just a little too low, I’ve started bumping up my fees. Instead of putting off a major money decision or conversation, I’ve been better at approaching them head-on, unemotionally.

My next steps

“Confidence is like a muscle. The more you use it, the stronger it gets.”

I firmly believe that your confidence will ebb and flow depending on how much you use it. While I know there will be days in my future where a negative internal talk track takes over, where I overthink simple decisions, or where my life feels like a mess, my confidence doesn’t need to take a hit. My goal is to continue focusing on small things each day to boost my confidence, so I don’t find myself relating to that horrible journal entry again.

Have you found something that works to boost your confidence? I’d love to hear.

*note: that is an affiliate link, but it’s a free tool I use and love and really wanted to share. For more information on affiliate links, see this disclaimer.

Photo by Imani Clovis on Unsplash


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