The Biggest Lesson I’ve Learned As An Entrepreneur

I recently did a Q&A over on Instagram and someone asked me what is the biggest lesson I have learned being an entrepreneur. I have so many things that I’ve learned, but the answer I gave was “just try it.” This is something that has been a philosophy of mine forever. Just try it out, see if you like it, see if it works, and if it doesn’t, at least you tried. You’ll never know until you try.

So I wanted to kind of expand upon that and share with you guys how I’ve done this throughout almost my entire life.

It all started with my love of writing. Bear with me here.

I’ve wanted to be a writer for as long as I can remember. Since I was a kid, I loved reading and writing. I would write short stories, books, scripts for pretend soap operas with my cousins and stuff like that. And so I always thought that when I grew up, I would be a writer.

But it was very hard to break into the writing industry back in the day. I would buy Writer’s Market and look up publications I wanted to write for and write query letters pitching my ideas. There were so many barriers.

Then the internet was born and I learned about blogging. I thought to myself, Why not just try it, get my writing out there in some way? So I started a blog in 2003 called You, Me & Five Bucks. Even though it never really popped off, I had a tiny little following, and it just felt good to get my writing out there.

And then something interesting happened.

When I was designing my blogs, I had to learn a little bit of coding. There were blog templates available, but I wanted to change it to a setup that I liked. So I taught myself basic coding. And people started asking me if I could make a website for them.

So I kind of accidentally got into web design. People were willing to pay me for simple web design, why not just try it? So I actually did web design for awhile. I also did some graphic design, like making logos, because I taught myself Photoshop and I was pretty good at that too. And so I had this whole web design / graphic design business for a while.

And then another interesting thing happened.

One day, in 2014 or 2015, I stumbled upon the planner community. I’ve been using a planner since I was preteen. My first planner was huge and teal and I loved it. After that planner, I moved on to Day Runner, then graduated to Franklin Covey, which was the rage back in the day. At one point I went more simple and I started using a Moleskine journal.

I remember I was looking for stamps to make planning easier because I was drawing my layouts every month. So I was looking for stamps to make it easier and I stumbled upon the planner community on Instagram. And then that’s where my life changed.

This was 2015, and I just really dove into the planner community. I bought all the Target page flags. I spent too much on Kikki K planners on eBay. I mean, I was all in, and then I remember that I was looking for inserts and I couldn’t find anything out there that fit my exact needs, so I just started making my own.

And then as I was posting pictures of those inserts on Instagram, people kept asking, where did you get those inserts? Can I buy some? And so I accidentally started an Etsy shop in 2016.

And then my sister-in-law bought a Silhouette Cameo and I thought it was so cool. I wanted to buy one to make stickers for myself because, again, I wanted to make my own designs to fit my exact personality, aesthetic and planning style. So I bought my first Cameo and I made my first stickers and, again, people wanted to buy what I was making. They saw it on Instagram. They asked how they can buy it. So I started selling stickers on Etsy.

I just decided to try it and if it failed, I would pivot and try something new. My writing wasn’t taking off, so I went into web design and graphic design. Then that kind of led me down the path to designing inserts and stickers.

Even after I got a certain level of success with The Planner Spot, I kept trying new things.

Like creating a YouTube channel. I’m super camera shy and would never be one to make videos. But I was watching all these plan with me videos and it seemed so fun and I wanted to share my planner stuff too. So one day I just decided I was going to try to make a planner video. My first one was super short. I didn’t talk on it. I didn’t show my face. I just showed myself planning.

I would’ve never known that I can do that. I would’ve never known that I could build a YouTube channel with a pretty decent amount of subscribers unless I tried it out. I figured that if it didn’t work out, then I could just stop.

I also tried out a membership platform which had some success and a podcast which is still in its development stage. But I would’ve never known if I would like it, if it would be successful, unless I tried it.

So that’s the super long version of my answer to the question: what is the biggest lesson I have learned as an entrepreneur? And I feel like if I didn’t have this philosophy of just try it no matter what, no matter how scared I am, no matter what people think, if I didn’t have this philosophy, I would 1000% not be where I’m at today.

And it’s not that I’m not scared of failure. Of course, I don’t want to fail, but what really hits me more is, but what if it doesn’t fail? What if it turns out to be great and awesome and life changing?

And the amazing thing about this journey is when I look back now, all of that experimenting, all of the trying things out, led me to where I am today. Nothing was a failure. Even the blog that didn’t really take off. Even this podcast that didn’t really go anywhere for a while. Everything that I’ve tried, all the things I learned along the way, I use in my business today.

So none of it was a failure. None of it was a waste of time. I use all those lessons in my business today, which I think is so cool. Like, wow, all this was leading me, the journey, all the steps, all the experiments were leading me to where I am today. And I just think that’s so amazing, and it’s all because I just tried it out.

I listen to a podcast from Cara Alwill called Style Your Mind. She had an episode one time where she said, “date your passions.” So you might have a bunch of different passions. I have a lot of passions: writing, design, organizing, and even content creating. Cara says date your passions, meaning try everything, try it all out, take it out on dates.

You can date all these different passions before you fully commit and you see what really works for you, what really clicks, where the chemistry is. And I feel like that’s really the essence of what I’ve been doing all these years. Dating my passions, trying it out, seeing if there’s really something there.

I really hope this reflection might help somebody out there that’s scared to try stuff, that doesn’t know if they can do it, that feels like who am I to do something like that? Trust me, all along the way I’m like, who am I to make inserts and stickers and sell them to people? I don’t know what I’m doing. Who am I to start a YouTube channel? Who wants to listen to me plan my stuff? Who wants to join a membership and support me as a creator?

All along the way I’ve had that imposter syndrome thinking who do I think I am. But the stronger push, the stronger motivation is, what if this can be great? What if this is what I’m meant to do? What if this is going to be life changing? And I think that’s even stronger than the imposter syndrome.

So I just encourage you guys just to go out and try it, just do it in small ways and don’t overthink it. Don’t wait to get the perfect equipment. Just try it out, do trial and error, pivot where you need to pivot, tweak and change until you perfect it, but just start. Just try it.

xo,
sam

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