Charge more. Charge sooner. Charge often.

I charged $750 for four days. It was worth $3000.

I recently held a small mastermind in Cabo for a weekend called #CaboPress – and it was awesome. People loved it. Everyone had a great time. And I heard one piece of feedback over and over.

“You should have charged more.”

And you know why I didn’t? Because I was nervous.

1. What if people didn’t like the place I picked (which was a personal favorite)?

2. What if people didn’t like the food?

3. What if people didn’t get enough out of it?

4. What if I couldn’t pull together all the transportation?

There were 100 ways things could have gone wrong. And none of them did.

But my fear got in the way of evaluating value. And doesn’t that happen to all of us. It’s why pricing is so tough – especially when we don’t bring outsiders into the mix to help us.

Because our own fears, driven by our insecurities, pushes our pricing too low.

Next time, I will charge more.

I’ve delayed long enough.

While I was at CaboPress, I met with some folks who I appreciate – particularly because they can challenge me. I went with the intention to help others. I’m pretty sure I got the most help.

The feedback was pretty simple: I wasn’t monetizing most of the work I was doing.

Now, to be clear, they weren’t talking about this site. They weren’t talking about my WordPress posts, or anything like that.

But my strategy, management and product development coaching weren’t being effectively showcased anywhere (which, by the way, was on purpose). Nor was it easy to purchase.

I bet you can figure out why, right? Because I was insecure.

I had limited what I was doing, and who I was helping, because it game me confidence and security that it wouldn’t be overwhelming. It’s a consequence of the impostor syndrome. And as a result, I’d delayed monetization for a long time.

But that’s what we do, don’t we? We let our nervousness delay when we start charging.

In my product world, I know better. We start charging people even as we’re building products. In one of our startups we charged people to get early access. In another we charged people from the beginning, with no freemium plans.

But personally, I haven’t done the same.

I should have started charging much sooner.

Clarity.fm – one place where I got it right

In case you wondered if this post was all about all the ways I was #doingItWrong, there’s good news. One place where I have figured out what works is with my use of Clarity.fm.

It lets people request a call with me, and allows me to charge them per minute, for as long as they want to talk. This has done two things:

1. It stops the people who want everything for free from taking up my time. The charge changes their behavior.

2. It allows others to make multiple requests without stepping into a formal agreement.

And it works. It works very well. And it turns out – people do use it, and some even come back a second or third time.

It took me a while to put it in place – because…you guessed it… I had a hard time believing strangers would want my advice and pay for it. Insecurity – the thing that ruins pricing algorithms the world over!

But I tested it, leveraged it, and watched people use it. Multiple times.

So I can tell you with full assurance: charge often.