Feel like you are getting NO better at this biz thing? 3 Questions to ask!

Today was a week of starting at the bottom.

I am a skillshare addict. There are so many classes to take and I am taking one in particular that is really challenging. LETTERING. BAH!

Now let me start off by saying that I am not a fan of being bad at things. I am all about putting yourself out there and trying but there is no way around feeling like you suck at something you really want to be good at.

Let me present to you, my very first lettering sketch.


NOT GOOD, right? NOT GOOD. I am in a class full of people who don’t actually NEED the lettering class. People who are really good and are mostly just showing off their skills.

To be honest, I’ve been a little shy to post. SUPER shy to get feedback and help. And I practice. I practice a LOT and I don’t feel like I am getting better.

I hear a lot of stories like this with my clients and friends.

“I am trying and it’s NOT getting better.”

“Everyone is better at this (busniess) and I can’t seem to get it right.”

“Shouldn’t something be happening by now?”

“I am not one of the IT bloggers.”


When I was in school, I used to take art and design classes and I wasn’t good. At least, not in the traditional way. I am not a “artist” in the traditional sense. I can’t draw. Or paint. And it used to drive me CRAZY.

BUT! I had a style. It was my style. I loved stories. And I loved typography. I would create little narrative stories and digital works that allowed me to play to my strengths. I loved to bring the real world online.

So I got better, but in MY own way.

When I first started my lettering class, I was trying to be like everyone else when what I SHOULD be doing is trying to find my own style and approach to lettering. That is what I am focusing on now.

Now, back to business. If you are trying and trying and not getting anywhere, check in with yourself. Are you trying to be like someone else and failing at that? Because if so, getting better at being like someone else will ALWAYS be hard. How about doing things your own way? What should “getting good” and “rising to the top” look like for you?

I remember when I was trying to “build my list.” It just WASN’T working. And then I asked myself a simple question:

What if I DIDN'T build my list? What if I just got to know more of the people on my list?

What if I tried to make my newsletter the BEST it could be every week?

And my list grew, my business got better and it was all in MY own way.

I am not saying that lettering will not still be hard for me but when you are in the zone and feeling authentic to yourself, you see progress everywhere. You FEEL like you are getting better. And it doesn't hurt so badly.

Here are some questions to ask yourself if your business just isn't working!

1. Could I do this better if I did it my way?

2. What does “getting good” really look like for me and my life? What do I really want?

This is so important. In my lettering class, a lot of my classmates are creating super curly and feminine type. That's not even my STYLE. Why am I even trying to do that?

3. What if I stopped pushing where I was getting the most resistance and focused on what I do best?

Are you desperately trying to build your list or sell one of your products? What if you leaned in somewhere else instead? What are you really rocking at right now?

4. Is this what you REALLY want? 

One of the hard truths of entrepreneurship is that a lot of people like the idea of working for themselves and don't really want the lifestyle that comes with it. It's the hard truth, yo. So check in with yourself. Do you want more of whatever you are doing right now? If not, ask yourself what else you could want. DOWNER. But totally true.


So, what do you think? Have you ever found yourself at the bottom and feeling crappy about it? Do you have any tips for people like me (haha) starting at the bottom and trying to keep the faith while trying to get better?


OH SNAP. Have you heard? It's IDEA TO INCOME time, yo! I have run this class 3 times and I LOVE IT! We even have a special new payment plan! You can sign up now for $95 dollars! AH! CRAZINESS!