What I Learned From My 38-Year Struggle with Contentment


About 2 months ago, I added a tagline to HER Style Podcast: Buy Less, Shop Smarter, Build a Wardrobe You Love. I’d be lying if I said that came naturally to me. When I let myself go on autopilot, I want to buy all the things. I shop with abandon. And my wardrobe gets out of control.

I’ve confessed my former shopaholic ways. I used to believe more was more when it came to my closet. I wanted options and to have a wardrobe brimming with trendy pieces! I never wanted to be photographed or seen in the same thing twice. I depleted my bank account many times on the quest to have it all.

It’s taken years of not only discipline, but discernment about what really matters to me, where I want to invest my finances, and learning the hard way that material possessions never satisfy. After 38-years, I no longer define my worth by what I own. But it’s taken a long time to get to this place.

In today’s episode, following on the heels of what I shared about my parallel battle with perfectionism, I’m diving deep into what I’ve learned during my lifelong struggle with contentment. If you’ve ever felt like you need something —anything– outside of you in order to feel happy, confident, or just plain peaceful, then pull up a chair, my friend. We have much to discuss.

❶ Less, But Better

I used to live by the “more is more” philosophy. I guess I was a maximalist before that was a thing. I wanted more clothes and accessories and friends and stuff and everything under the sun! I wanted options, especially when it came to clothing (for obvious reasons) and friendships, because I was burned quite a few times in my past and felt scared to invest deeply in any singular friendships for a long time. But this approach to life led to a lot of stress and burnout.

So many things and people to care for! I was spread thin, I had too many options, and I was overwhelmed. This happens, right? We cram our closets full of stuff, we put off doing the closet audits over the years, and we don’t even know what we have anymore. We end up with too many things and yet, nothing of quality or certainty. We have a closet full of clothes and nothing to wear or a calendar of events and then feel so lonely at the end of the day.

Thankfully, I’ve learned this is NOT how I want to live my life. I’ve recognized the value in having less, but better. I’ve worked to upgrade the quality of my wardrobe, my relationships, and even my work. I’ve taken out a lot of the fluff that kept me busy but not productive (one of those being a focus on social media). In a sense, I’ve learned to prune my life. I’m slowly removing the things that don’t bring me joy, help me to grow, or align with what matters to me. 

This might sound deep, but that includes what’s in my closet! I still have a good amount of pieces and I don’t consider myself a minimalist. I’ve found what feels like a healthy middle ground. I have options and I have some pieces that still aren’t the most amazing quality, but I love and wear what’s in my closet. I don’t wear things once and toss them aside. I don’t feel like I need more just for the sake of having more. I put thought and intentionality into what I buy and getting dressed has never felt so easy or fun.

❷ My Worth Isn’t In What I Own

I used to measure my success and self-worth based on my accumulation of stuff. I had the goal of buying myself a Land Rover, because that was what the #1 salesperson at Saks Fifth Avenue drove. For years, I didn’t consider myself to be successful because I hadn’t attained that milestone.

Heading into my 39th birthday, I finally want to live MY life, not someone else’s.

Last week, I talked about how I can get caught up in social media and I mostly stay off Instagram these days. Because while I can be easily inspired, I also get distracted and depressed by what I see. It’s easy to want what other people have or to think they’re better than me because they have better clothes or a bigger budget or look perfect on the outside. They seem to have it all. And so I have to remember that their worth and mine is not in what I have or what I own or even how I look. It’s not in anything external. This has been a really hard lesson and one I still remind myself of daily. 

We don’t need to prove ourselves or accumulate more belongings in order to do so. I’ve never valued a friend because of what they had, I value them because of who they are. So these days, I strive to be a better and less self-centered human, caring less about what I have and more about what I have to give. 

❸ Stuff Never Satisfies

My husband and I hit a big financial milestone about 2 years ago. And do you know what? Nothing changed. We didn’t feel any different.

We put so much stock in hitting our goals or wanting “the thing”. But once we have it, what happens? We quickly move onto the next. We didn’t even take time to celebrate. 

You might’ve heard me talk a little bit about my faith as a Christian on the podcast before. No matter your religious beliefs, I think we can all agree that material things only bring us joy for a moment. 

In John 4:13-14, Jesus is talking to the woman at the well and he says, “Everyone who drinks from this water will get thirsty again. But whoever drinks from the water that I will give him will never get thirsty again. In fact, the water I will give him will become a well of water springing up in him for eternal life.” 

This is such a beautiful reminder that our belongings will never be enough to satisfy us.

❹ Contentment Is an Attitude

Just like confidence is a choice, contentment isn’t about what you have or don’t have; It’s all in how you’re thinking about and relating to what you have.

When we were going through our 6 year infertility struggle, I was miserable and depressed during a significant chunk of that time. I felt so much lack and envy for other women who seemed to be posting baby announcements left and right. I felt a huge void in my life. All I could think about was how great everything would be when that time finally came for us. 

And I can’t even remember now what shifted things for me, but over time, I started to surrender. I realized that life was too short to spend it waiting and wishing. I wanted to live now and be happy in my circumstances. So I started to be grateful for all that I had. I started practicing gratitude and my contentment shifted right into place. My circumstances hadn’t changed, but the way I was relating to them did. I slowly started to enjoy my life again.

Looking back, that time was amazing and I’m grateful now that we didn’t have our son until 2018, 10 years after we were married. It was a decade full of ups and downs, but I learned during that time that contentment is an attitude and it’s something I can feel no matter my circumstances. There is always something to be grateful for, especially looking back.

❺ Keep Your Priorities In Check

Growing up, I must have driven my poor parents crazy, because (like many kids) I asked for everything. There was always something I wanted. And I was generally convinced that life would be better, I’d be cooler, and all would be right in the world when I finally got THAT THING. Of course, if and when I ever got that thing, I’d move right onto the next.

Embarrassingly, or maybe relateably, I’ve been much the same way in my adult life. I’ve wasted a lot of money on the wrong clothes and a lot of time over the wrong priorities. It’s taken maturity, growth, and perspective to realize what’s most important to me. When I get to the end of my life, I won’t look back wishing I had bought that jacket or spent more time and money on my wardrobe. I know I’m going to reflect on all the relationships in my life, the people who impacted me and who, if I’m fortunate enough, was able to impact as well — my family, my friends, my clients, maybe even a blog reader or two, like you.

It won’t matter if I had a closet full of designer handbags or what I wore to this wedding or that one. Yes, I enjoy shopping and getting dressed. I believe clothing can be beautiful, enjoyed, and appreciated. But I want it to be in the backdrop of my life, not the main focus. 

I want us all to have wardrobes we love. The right clothing can help you feel more confident, project a more accurate story about who you are to the world, land you opportunities, and make your life a lot more fun! But I don’t want it to be everything to you. Please don’t get caught up in needing to have more or defining yourself by what you have. 

At the end of the day, your wardrobe matters, but it doesn’t matter most.


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