5 Ways Cutting Your Hair Can Help You Grow as an Entrepreneur

Olivia Lee
8 min readApr 16, 2021


My hair has always been super duper long, but last year, I chopped it all off. Can’t even tie it anymore. It was my first time having my hair this short. And let me tell you, I love it. So today I’m here to talk about five ways on how cutting your hair can help you grow as an entrepreneur.

First of all, cutting my hair this short has helped me so much with my productivity and time management. And I’m sure that’s pretty self explanatory, especially for someone like me who has a lot of hair. It took me so long to wash, dry, and style, but if I didn’t, my hair would end up looking so messy. My nickname used to be Korean Hermione because my hair was super long, and there was just so much of it that. It was just not a cute look.

Korean Hermione Granger

But short hair has helped me save so much of my time because I come out of a shower in less than five minutes. I’m saving the environment by using less products, less water, and less heat on my hair. Now, with a lot of my meetings online because of the pandemic, it’s so easy because all I need to do is dry it, put on a shirt and then just sit in front of the computer (maybe put on pants if I feel like it).

And second of all, having short hair is helping me stay better focused on what matters. Yes, you want to look presentable on camera because that’s one of the factors that catches people’s attention. You want to be clickable. You want people to see your content, but on the other hand, it just helps me focus on giving more value instead of focusing more on how I’m going to look on camera. It’s so liberating! When I had long hair, I was so worried about how I would look on camera, which is probably the reason why I didn’t make that many videos in the first place.

I was really self-conscious. I feel much more confident now. Short hair really helps me to embrace myself the way I am and focus on value driven content, more than looks.

Third of all, it’s very empowering. I’m giving myself the authority and power to make my own decisions. Despite followers telling me, “don’t do it! You’re going to look so weird!” If I’m true to myself, I like being a little rebellious. So when people tell me not to do something, I think, “who are you to tell me not to do something? I’m going to do it.” Even though I always wanted to, I’ve never cut my hair this short. And I am so proud of myself for making the decision to actually go through it. I hate the feeling of regret, so I would rather make a mistake than to regret that I’ve never done it before. The only way for me to know if I’m going to hate it or not is to actually try it and then see it for myself. And it really helps me to care less about what other people think and not letting other people define me based on my looks.

Photo by Adam Winger on Unsplash

It really shows the difference in the way people support you. When I announced I planned to chop off all my hair, my friends were excited for me, but a lot of my followers were very outspoken against it. “Don’t do it. You’re going to look like a little boy. I’m going to unfollow you, blah, blah, blah, blah” That really helped me realize, Hmm, were they just not listening to the value that I had to share, but were they only following me based on my looks? Having an online presence sometimes comes to a lot of people trying to talk over you and telling you what to do. People have a lot of opinions. People have a lot to say, but don’t let those people decide on your life. Even if it’s just a little decision, like cutting your hair, are you going to listen to what other people tell you to do in the future when growing a business or deciding who to date?

And number four, it can help you look more professional. Everyone is different. I have half curly, half straight hair. I have a lot of hair and my hair was super long. And every time I went to a meeting, my hair was a huge distraction. Not only for myself, but for my potential clients or my partners. There was one time when I was having a meeting, and that’s when my hair was like almost down to my belly button. And there were these little candles on the table. As I stood up to leave after the meeting was over, my hair caught on fire. I definitely made an impression that they’ll never forget as “the girl who caught her hair on fire.” That just showed me how messy hair can be a huge distraction. And when we’re eating food, I would find strands of hair on the table or stray strands finding a way into to my mouth. It became one of those awkward moments of are you going to get the hair out or are you just going to eat it to avoid awkward moments. Maybe that was a better idea, but instead I decided to pull it out. But in that moment I made eye contact with my client. So we were staring at each other as I was pulling hair out of my mouth. In conclusion, it definitely helps me stay focused on the meeting and adding that spark of professionalism because I no longer have to get the hair out of my way or flip my hair or be distracted, tying it or getting it out of my face or out of my mouth, et cetera. So that definitely helps. And personally, I think shorter hair makes me look more mature and more my age.

I always spent a lot of time getting ready, making sure my hair was done. I had enough makeup on to make myself look professional, but there was a lot of focus and time that was wasted into focusing on my looks, which doesn’t really matter. Because if you’re trying to do business, people don’t really care about your or they shouldn’t care about your looks day, should care more about the value and the outcome that you bring, which goes back to the second point that I had when I said it helps you focus more on value driven activities. To me, at least it becomes less about how I look and more about how I can help you and how I can actually bring the value and outcome that you’re looking for.

On to number five, and that is starting a fresh new look. I’m all about growing a personal brand through impactful content. And I am ready to embrace this new image and new look of me and tie it back to how to utilize the new look into growing a personal brand. So I highly recommend that you try cutting your hair and see if you’ll like it, or see if it represents who you are better. And it can even be a story or content in itself, like what I’m doing now, because of all these things that I learned just by cutting my hair. And for those of you who have always had short hair, I have a lot of respect for you. First of all, it might not be a big deal, but for someone who’s always had super long hair for years, to cut my hair, was revolutionary for me.

And that’s why I’m so excited to talk to you guys about this and share what I’ve went through with this haircutting journey. So take everything as a learning experience and ask yourself, what did I learn from this? How does it make me feel? I think those two are very important questions for all of us to get to know ourselves better and be more self aware. And as a bonus, I just wanted to share that by cutting your hair, you’re still the same person! It’s kind of like changing your clothes. You’re still the same person. It’s just a different look that you have on. Now, if you realize that you’re embarrassed after cutting your hair or don’t want to go outside, et cetera, don’t regret that decision, but rather ask yourself like, Hmm, why do I feel this way? Is it because I care too much about what other people think? Or is it because you just look better with long hair? That can be the case as well, which is my other second bonus point: having short hair can help you be more patient. It’s no magic. Your hair doesn’t grow overnight. It takes time to grow. I think it’s going to help me be more patient because even though I want it, even though I want my hair to be a little longer, I know it’s going to take time. Then I can focus on value driven activities that will grow my business. So, no excuses there, and your hair will look healthier and be healthier. I stopped dying my hair a while ago, but man, in the past, I was crazy about dying my hair, all kinds of colors. Like I dyed it blonde on platinum blonde, red, orange, my gosh, I look like those Kpop stars because my hair was super colorful, but it also felt like a broomstick having thick hair. I had to bleach my hair eight times. I know it’s unbelievable and very unhealthy. I had all kinds of split ins. My hair looked like a broomstick and felt like a broomstick. Cutting it all off is so liberating. And it’s a new start because I don’t have any split ends. This is a hundred percent my hair without any chemicals or products in it. And I love it. It feels so healthy and I’m loving it. And who knows, you might end up loving your new look.

Photo by Michael Dagonakis on Unsplash

So those are five ways and some bonuses on how cutting your hair can help to grow you as an entrepreneur. If you decide to cut your hair, make sure to take a photo and tag me on Instagram @livyounglee, I would love to see your new look and hear all about how it made you feel. And if you have any other ideas on how cutting your hair can help to grow your confidence or help to grow you mentally as an entrepreneur, make sure to comment so that other people can read and feel inspired by some of the things that you have to share.



Olivia Lee

Uplifting Introverts to Become Confident Leaders, Captivating Storytellers, and Charismatic Speakers without any previous Public Speaking Experience.