The Big 3 Takeaways from My First $20

I can hardly recall what I had for lunch earlier today, but I will never forget the first time I earned $20.

Free work yielded a referral, and I got a call a few days later. He told me about what he wanted, his vision, and how long he had before he needed a design. Everything was smooth. Until….

“What do you charge?”

“Um. Well. Uh……”

A few more seconds of frazzle.

“I guess $20 an hour. It’s probably a four hour job,” I said shakenly.

Truth be told, I had no idea how long it would take. I did, looking back, a moderately good job. This small sale put me on a whole new journey, one that I’m still on today.

So let’s dive into some lessons learned while reflecting on the origin of it all.

I made a ton of mistakes selling my artwork and graphics, learning to coach (which is selling my product to parents and delivering to youth – a complex business scheme) and building a revenue tracking system for a large corporation.

I learned faster when I messed up, versus when I was successful. Mistakes force you to adapt NOW.

My first $20 taught me three things, the hard way:


  1. If I’m going to make money doing something, I have to take myself seriously and project that.
  2. Before I sell anything, I should know what it costs to do so, whether that be time or supplies.
  3. If I’m not ready to name a price and offer my services, I don’t have to. I can make the proposal in the way that I’m comfortable, where I can articulate my ideas well, but I have to approach it the right way.

That’s not to say that success isn’t awesome, either. I know that I would have killed for some input on a second income when I got started, just to know someone else was feeling the same way. With success comes a lot of things, and I remember these three awesome thoughts that I hope you have too:

“I can make money doing something I love”

“I got paid to do this, and I don’t have any education in it.”

“I am not even that good yet. Imagine if I could get 10x better what I could make.”


Let’s get straight to it:



  1. Be More than a Hobbyist

 If you’ve come here to side-stream, or to improve it, you need to make sure you are always using this word in conversation when you bring up your talent, work, passion, or job.


Professional: (n) – engaged in a specified activity as one’s main paid occupation rather than as a pastime.

I met two clients after starting just from putting my profession out there when they ask what I do. I am quick to distinguish what I’m doing for money (ex. presentations) from what I do for fun (ex. snowboarding).


Here’s an example:

Brian: “I’m a dog walker for big breeds in the Norfolk area.”

Frank: “I’m a professional dog walker for big breeds in the Norfolk area.”

At this point, Brian is saying “I’m a hobbyist.” There’s nothing wrong with that, unless he’s trying to earn money from this approach. I know absolutely nothing about dog walking, but I know Frank is making money doing it and that he’s got an area and a type that he serves.

Whether you are making $3 or $3MM, you are a professional– you do your work for an exchange of cash.

You want the fact that you do your craft, love or solution for money conveyed and yes, you say it even if you haven’t sold anything, yet. It is an important distinction.

As Side-Streamers, we should be projecting that we do this for money and we have a specialty. Put it out there.  People want your help, your expertise and your ideas.

Don’t just say that you’re a photographer. Tell them you’re a professional photographer and you do family shots at carnivals. I’m not a presentation guy; I’m a professional presentation designer that loves to spice up talks for persons of interest. Don’t make it up, but share it!

It’s awkward at first – work through it and continue to use it. The more you say it the better it will feel and the more it will resonate.

How many times have you heard someone say: “Maybe we should hire a professional,” or something to that effect. You want to be in that group, so assign yourself that title.

Bottom Line: Use the word professional and mention your specialty.


  1. Know Your Costs

When I got asked my hourly rate, I was on the spot and nervous. I didn’t know, so I sold my time for $20/hr. That one worked out. But only because my service didn’t involve costs at that point.

Fast forward a year, to where I was doing some digital paintings on the side. I posted a shot on Facebook, and got a request from a friend for a copy. I was so excited. $30 I screamed!

Turns out printing was $20, and shipping was $8.

Print, Pick Up, Pack, Ship, Cash Check = $2 Profit. Wow.


I don’t like focusing on what I’ll get out of a client initially, after all, that’s what makes me a good Side-Streamer. I want to be obsessed with knocking my service out of the park!

Still, you need to know, roughly, what things will cost when you take on a project. Remember, information is EVERYWHERE. What supplies do you need? What software are you using? What about travel time? Sometimes it’s not that easy, but I urge you to take time to write it all out. (If you’re on the spot, see takeaway number 3!)

Am I telling you to have a figure down to the cents of it – no. But if someone says, I’d like you to build a presentation for my 5-minute talk, I know it will take me a few hours of image editing for that length of time in a presentation, and even more the arrange the images in a logical display. I can’t quote him a $100 pricetag. I won’t do well on an 8-hour project.

Bottom Line: Get familiar with your costs to produce. Maybe it’s zero, $40 per transaction, $15 in shipping per sale, or a flat space rental of $50/hr. You can’t earn until you know what the cost is!



  1. Carrot & Stick Technique: Displace Estimate & Beat Competition

If you don’t know the guy that rambles and quizzes you about a project and 30 seconds later says, “What will it cost?” then count yourself lucky.

Many numbers people will try to intimidate you to do complex math like you’re Stephen Hawking.

See, I won’t forget this guy. I had quoted him $20/hr for four hours. It took 10. I wanted the job, but I lost my balance back from that overly type-A question right in my face. I wasn’t prepared.

The Carrot-and-Stick Technique relies on you having good communication, and it’s a two-part process.


The CARROT… (at the meeting/phone call/etc.)

I think better about my work not standing in front of someone, so I make sure I’m give myself the chance to do that. If I’m asked for an immediate quote, I say something like:



“Before I give you a price I’d like to ask you some questions,

get a feel for what you’re asking for exactly, and then map out my idea and what

it could cost. You’ll have a full idea of what I would do and an accurate estimate of the cost.

I’ll get your email and I will send you a full description and proposed price later today/tomorrow/reasonable deadline.

How’s that sound?

Notice, I made this entire thing about him. I didn’t say – “I need to calculate my potential earning at home.” It’s about me giving him a fair rate and great service. [Bonus Point if you work professional into this kind of statement]

As a Side-Streamer it’s important we make EVERYTHING about our client. (Join the email list and learn ALL about this in the Guide to Price Your Side-Stream)

Simple fact of business – if someone is paying me, it doesn’t matter if I love it, it matters that they do. You have the tools to nail it right here:  Read the Boomerang Technique to prevent missing what they want from your service

A few here and there will demand a price on the spot. I manage to give them a fair range, but ask for a moment to think, go to the bathroom, or pop out a cell phone and do some math. “I can give you a best guess range, and then follow up with more details later.” I tend to overinflate these numbers if they are pushy, just because they are being difficult.


The STICK…(the communication before the pitch)

There’s no easier way to beat competition than by great communication. Send an email when you get home to thank them for meeting with you, like this:


“Hey ____________.

 Thanks for meeting with me yesterday. I’ll be working on your estimate today

and will get it to you as promised by [deadline you gave].  If you have any questions

in the meantime, feel free to ask them!”

It’s an easy a business gesture shows you listened. You want a happy customer experience from the meeting to the quote to the estimate.

As you lay groundwork for a good relationship of service to your client, build your pitch around what you already know about him or her.

Next, you’ll send him your estimate, and don’t think you have to have a perfect excel file emailed to him – do what makes you comfortable. If you’re better with numbers, use numbers. If words suit you, do it! When you email someone your price, you’re sending them a pitch or proposal. If all you do is write a dollar amount, you’re missing a HUGE opportunity.

Don’t be afraid to really put time into your pitch. They will notice. For high conversions on a proposal, read my guide here.

Bottom Line: If you’re pressured, put the game back on your terms by effectively communicating with your client.




In essence, I learned that:

– There are people that want me to do free work, but I dispel them quickly; I’m a professional.

– Making money requires spending money. If you know what you would spend, you’re set to earn.

– Communication and a two-step approach are identified with high-value service.



What did you learn from your first Side-Stream money?

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