Ep. 2 | Freelance Cake Podcast
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Episode 2|

How Debt & Desperation Led to Value-Based Pricing & Selling Strategy

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In Episode #2, Austin L. Church reflects back on a difficult season in his career in the fall of 2015. During a trip to Florida, he discovered that he and his wife were spending more than he was earning. They were back in debt.

Austin had been binge-listening to Brennan Dunn’s Double Your Freelancing podcast, and several ideas Brennan shared became the next freelance experiments Austin tried. Instead of doing discovery sessions for free, he tried selling strategy as a standalone offer.

This one move put his business on a whole new trajectory. Sometimes, we need a breakdown to have a breakthrough.

Notable Quotes

"I haven’t had the Midas touch. And if we’re using mythical people, I have felt more like Sisyphus pushing a boulder up a hill."

“Go find your most valuable aptitudes, not just your most valuable skills.”

“Maybe why I really appreciate the people online who share all of the good, bad, and ugly in their stories is because my story has had some ugly too... I often find people’s failures more relatable than their successes.”

Perfect Start to Their Journey? Not My Story

Too often, we hear stories online that are carefully edited and polished. They’re kind of like Cinderella stories, except it’s all Ella and no cinder. The cruel stepmother and the awful stepsisters are missing along with the self-doubt, fear, anxiety, and all of the other stuff that makes stories interesting.

The same way Photoshop erases the wrinkles and blemishes from your headshot, the right personal branding framework and copywriting removes the dead-ends, detours, and discouragement from your story.

Your smile is now effortless and your teeth are blindingly white.

The last 6 years of your life are now an elegant and smooth story arc instead of the real tangled mess of circles and knots (that's what they would look like if you drew them on paper).

“I overslept and made another million dollars by accident. Oops!”

That is not my story. I haven’t had the Midas touch. And if we’re using mythical people, I have felt more like Sisyphus pushing a boulder up a hill.

“Is this it? Are things ever going to get any easier? Surely, there must be a better way to build a business?”

The Deflating Debt Discovery at the Beach

So, let me take you back to September 2015 when I found out that we were in debt (again).

I was driving down to Florida with my family. We were headed to the beach…

Now, before you get all judgy on me and think “Is this guy gonna talk about this crisis he had while at the beach?”... well yes, that’s exactly what I’m gonna tell you about.

The worst thing to do is be the grumpy guy at the beach. Everybody else is having a great time. Austin was sitting there preoccupied because he’d made a really unfortunate discovery.

I’d opened up my online banking and what did I find?

We had carried a balance. We did not have enough money in our checking account to cover our credit card balance. That meant we were back in debt, again.

That was really discouraging for several reasons. Number one, in August 2013, we had just finished paying off our debt.

It was a huge victory. It was a financial victory. It was a moral victory. It seemed to put us on this trajectory that we had never been on before. 

”Oh! We’re the people who are living debt-free. We’re the people who are making prudent financial decisions”, or however your grandad would say it. I’m sitting at the kitchen table in this house and I felt so deflated.

Because I had taken $25,000 out of my savings and invested in a startup I had co-founded called Closeup.fm. We had a really cool mission. We were going to help grow the middle class of musicians and artists.

However, even though I have no regrets, the startup was eating up all of my time. And it wasn’t paying any of our bills.

So I was working for free for the startup and trying to get my family’s bills paid by freelancing on the side.

Not Following Any of the Best Practices I Already Know About

I think I had taken my eye off the ball because I hadn’t raised my freelance rates in over two years.

I’d let my client base go stale.

Maybe you’ve had that experience yourself where you’re just running and gunning. You’re working on freelance projects. You barely lift your head up to take a look around and take stock of your surroundings.

And when you finally do, you see that there are some major problems in your business. Maybe I had to get on a vacation before I could really reflect.

Well, when I started to look around and reflect, I realized “Wow! I’m not following any of the best practices I already know about.”

I had become dependent upon one or two big anchor clients to supply most of the freelance income I needed. When one of those clients left or maybe the work just started to taper off or dry up, now you have a month where you don’t hit your income target, and then another month…

And suddenly, it’s not just one bad month. Suddenly, you have this downward trend.

And it’s not suddenly – it’s like I’ve had months to notice this but it all kind of crowded in on me in September of 2015.

I wasn’t making nearly enough money for my family. We were back in debt. And on top of all that, where was the time gonna come from? As soon as I start taking a little bit of time away from the startup, well now I have divided loyalties.

I’m supposed to be a good sport. I’m supposed to be happy. I’m supposed to put on that smile at the beach. My mind is spinning because like I’m not even supposed to be working right now. I’m not supposed to be problem-solving.

From $30K Months to Living Paycheck to Paycheck

If I’m gonna be really, really transparent, I felt like a failure. I was the primary breadwinner for my family but I had fallen asleep at the wheel. My earnings had gone down. I’d barely noticed it and now we were back in debt.

To put it in context, I had had several $20,000 and $30,000 months. I don’t say that to give myself a big pat on the back as much as to say “My! How the mighty have fallen.”

So now, we are more or less broke, living month to month, in debt. And that was embarrassing to me.

You should know that some of my freelance work at the time was marketing and growth coaching / consulting / training for clients.

It’s really hard to show up and be a confident consultant when you know that you’ve got all this debt. How am I supposed to sell my expertise to another person if I can’t solve my own problems?

My confidence had taken a huge hit.  I just felt like as a provider and as a husband, I was not scoring high marks.

So, my takeaway was:

  • I need to make more money.
  • We have kids so our financial needs are going to keep growing. They’re not going to get smaller anytime soon.
  • Because my time is so limited with all of my responsibilities with the startup, I really needed to make more money in less time.

In the past, when I had plenty of time on my hands, it didn’t seem like too big of a loss to do marathon discovery sessions with the client.

You want to meet me at a coffee shop and unpack every business problem that you’ve ever had and maybe eventually, I can find something in there and wrap a proposal around it?

Sure, what time?

I didn’t have that kind of time anymore. I could literally not afford to do long discovery sessions for free.

Being spread too thin and being short on time, I needed a better way to onboard clients and put together proposals that had a reasonable shot of getting a yes.

The Road Trip That Led Me to the Idea of Getting Better Leverage in My Freelance Business

What I didn’t mention was that earlier, when we had been driving down to Florida, I had put in my headphones and started binge-listening to a podcast called the Double Your Freelancing podcast. The host was a brilliant guy named Brennan Dunn.

Brennan is a software engineer and he started talking about this thing that he did with his potential software clients called roadmapping.

Essentially, he’d sit down with them and use Socratic questioning which I’d learned about in high school. He would ask them questions, consult with them, and do what I now call Uncover the Buried Dartboard.

Often, a client will get in touch with an initial request. If you ask good questions and keep peeling back and uncovering the full scope of the problem, need, or opportunity, what the project ends up being is very different than that initial request.

So maybe I was looking at a solution to my first problem which was “I am over these marathon discovery sessions where the client just talks on and on and I have to keep them on track.”

What if we just turned that into a paid engagement? What if helping a client get clarity around what the project even is - well, that’s the first project, it’s project strategy!

You’re helping the client figure out the group of decisions that the client needs to make to get from where they are to where they want to be.

This dovetailed nicely into something else I had been wanting to try which is value-based pricing.

As a freelancer, you have the creative skillset that gets you into freelancing. That skillset might involve writing, graphic design, coding, illustration, photography, or filmmaking.

But what about value-based pricing? How do you charge based on what the project is worth to the client and not charge based on what everybody else in your industry charges?

Perhaps paid discovery or project roadmapping could be that bridge. If I positioned myself well, if I priced the engagement well, I could decouple time and money. I could charge based on the value of the clarity and confidence and actionable plan.

Getting Paid for Offering Strategy for the First Time

When I got home from the trip full of discouragement, I had just enough gumption to think “I have got to start trying this.”

So, that’s what I did. I started trying. And I did not sell successfully my first paid discovery session until April 2016. But I’m going to tell you right now it was a before-and-after moment for my freelance business.

It put my business on a whole new trajectory because I got one yes from a client. And that one yes from a client proved that people will pay for other aptitudes.

They’re not just interested in my hands. They’re interested in my head.

They’re not just interested in my creative skills, they’re interested in my thinking, in my problem-solving ability, in my ability to research and sympathize, and connect new dots for them.

They’re interested in my point of view: I bring outside perspective so things that seem so obvious to them… I can come in and say:

  • “I really think that you should get rid of that obstacle”, or
  • “I really think that this is the wrong project”, or
  • "I really think that you should fire your business partner”

Getting better results with less effort in the form of project roadmapping and value-based pricing totally transformed my freelance business and opened my eyes to other possibilities for better leverage.

You might say that my whole journey with better leverage began with that crisis at the beach and trying to sell strategy as a standalone offer more as an act of desperation than anything else.

Maybe why I really appreciate the people online who share all of the good, bad, and ugly in their stories is because my story has had some ugly too. I often find people’s failures more relatable than their successes.

That’s one of the reasons why with this Freelance Cake podcast, it’s really important for me to share my failures, fumbles, mistakes, and embarrassments with you too.

Most of you probably can relate to sitting down at a kitchen table, kneading your face, pulling your hair, and thinking “How on earth are we gonna pay our bills?”

“Go Find Your Most Valuable Aptitudes, Not Just Your Most Valuable Skills”

I hope this story has woken you up to the possibilities not only of what the future may hold, even if you feel a little bit desperate right now, a little discouraged, or a little deflated; hopefully, this story brings some encouragement.

And hopefully, you’re waking up to the possibilities that some of your better leverage will come not from the creative skills that you’ve got but from your other aptitudes.

Writers sell writing then use those aptitudes I’ve mentioned to deliver it. Consultants sell those aptitudes then use writing to deliver them.

You already have the same aptitudes that many of the highest-paid consultants in the world have, you just haven’t learned how to sell those aptitudes yet.

So if I have motivated you today to do nothing else, at least let me motivate you to do this:

Go find your most valuable aptitudes, not just your most valuable skills.

You can sell strategy as a standalone offer.

The future may be way brighter than you realized but if you keep going and take a look at your aptitudes and make an inventory of them, we often get better leverage from repackaging aptitudes rather than trying to find a new way to sell creative skills.

Do You Want Help Getting Better Leverage in Your Business?

Be sure to check out the Freelance Cake coaching program. We have group sessions, a private community, and on-demand trainings.

Each week, you focus on implementing a specific lever such as your positioning cheat code, juicy offers, or morning marketing habit.

The same or better income with more free time, fun, and creative challenges - that’s the point, right?

Links and Resources from this Episode

freelancecake.com/coaching

Episode Transcript

[00:00:00] Welcome to the Freelance Cake Podcast. I'm your host, Austin L. Church. The goal of this show is to help full-time, committed freelancers get better leverage.

[00:00:13] As the sworn enemy of busyness and burnout, I have no desire to see you work harder. Instead, I reveal the specific beliefs, principles, and practices you can use right away to make the freelance game more profitable and enjoyable. So chill out and listen in, because the best is yet to come.

[00:00:37] Before we go too much further with this idea of getting better leverage in your freelance business, I want to give you some backstory.

[00:00:45] Too often online, we hear stories that are carefully edited and polished. They’re kind of like Cinderella stories, except it’s all Ella and no cinder. The cruel stepmother and the awful stepsisters are missing along with the self-doubt and the fear and the anxiety and all of the other stuff that makes stories interesting.

[00:01:11] The same way Photoshop erases the wrinkles and blemishes from your headshot, the right personal branding framework and copywriting removes the dead-ends, detours, and discouragement from your story. Your smile is now effortless and your teeth are blindingly white.

[00:01:30] The last 6 years of your life are now an elegant and smooth story arc instead of the real tangled mess of circles and knots (that's what they would look like if you drew them on paper).

[00:01:43] “I overslept and made another million dollars by accident. Oops!” That is not my story. I haven’t had the Midas touch. And if we’re using mythical people, I have felt more like Sisyphus pushing a boulder up a hill.

[00:02:05] “Is this it? Are things ever going to get any easier? Surely, there must be a better way to build a business?”

[00:02:13] So, let me take you back to September 2016 when I found out that we were in debt, again. So I want to take you back to September 2016 when I was driving down to Florida with my family. We were headed to the beach - now, before you get all judgy on me and think “Is this guy gonna talk about this crisis he had while at the beach?”, well yes, that’s exactly what I’m gonna tell you about.

[00:02:43] The worst thing to do is be the grumpy guy at the beach. Everybody else is having a great time. Austin was sitting there preoccupied because I’d made a really unfortunate discovery.

[00:02:59] I’d opened up my online banking, I’d opened up my credit card and what did I find? We had carried a balance. We did not have enough money in our checking account to cover our credit card balance. That meant we were back in debt, again.

[00:03:18] That was really discouraging for several reasons. Number one, we had just finished in August 2013 - I say “just”, it wasn’t yesterday - but a couple of years before, we had finished paying off our debt. It was a huge victory. It was a financial victory. It was a moral victory. It seemed to put us on this trajectory that we had never been on before.

[00:03:43] ”Oh! We’re the people who are living debt-free. We’re the people who are making prudent financial decisions” or however your grandad would say it.

[00:03:53] Anyway, I’m sitting at the kitchen table in this house and I make this discovery and I felt so deflated. Because number one, I had taken $25,000 out of savings and invested in a startup I had co-founded.

[00:04:13] The startup was called Closeup.fm. A really cool mission. We were going to help grow the middle class of musicians and artists. And even though I have no regrets - had no regrets then - the startup was eating up all of my time. And it wasn’t paying any of our bills so I was working for free for the startup trying to get my family’s bills paid by freelancing on the side.

[00:04:40] And I think I had taken my eye off the ball because number two, I hadn’t raised my freelance rates in over two years. I’d let my client base go stale. And maybe you’ve had that experience yourself where you’re just running and gunning. You’re working on freelance projects. You barely, you know, lift your head up to take a look around and take stock of your surroundings. And when you finally do, you see that there are some major problems in your business.

[00:05:16] So when I lifted my head up and looked around, maybe I had to get to a vacation before I could really reflect. Well, when I started to look around and reflect, I realized “Wow! I’m not following any of the best practices I already know about.”

[00:05:34] I had become dependent upon one or two big anchor clients to supply most of the freelance income I needed. When one of those clients left or I forget which, maybe the work just started to taper off or dry up, regardless, you have that month where you don’t hit your income target and another month.

[00:05:56] And suddenly, it’s not just one bad month. Suddenly, you have this downward trend. And it’s not suddenly. It’s like you’ve had months to notice this but it all kind of crowded in on me in September of 2016.

[00:06:11] You know, I wasn’t making nearly enough money for my family. And we were back in debt. And on top of all that, where was the time gonna come from?

[00:06:21] As soon as I start taking a little bit of time away from the startup, well now I have divided loyalties. So, I’m supposed to be a good sport. I’m supposed to be happy. I’m supposed to put on that smile at the beach. And my mind is spinning because like I’m not even supposed to be working right now. I’m not supposed to be problem-solving.

[00:06:45] So, you know, if I’m gonna be really, really transparent, I felt like a failure. I was the primary breadwinner for my family. I had fallen asleep at the wheel. My earnings had gone down. I’d barely noticed it and now we were back in debt.

[00:07:05] To put it in context, I had had several $20,000 and $30,000 months. I don’t say that to give myself a big pat on the back as much as to say “My! How the mighty have fallen”, right?

[00:07:19] So now, we are more or less broke, living month to month, in debt. And that was embarrassing to me. You should know that some of my freelance work at the time was marketing and growth coaching slash consulting slash training for clients.

[00:07:38] And it’s really hard to show up and be a confident consultant when you know that you’ve got all this debt. How am I supposed to sell my expertise to another person if I can’t solve my own problems?

[00:07:55] And I know it’s never that binary, right? People who have problems - even problems in the area around where they consult - can still give meaningful and valuable advice. But my confidence had taken a huge hit.

[00:08:10] And yeah, like I said, I just felt like as a provider and as a husband, I was not scoring high marks. So, my takeaway was I need to make more money. We have kids. Our financial needs are going to keep growing. They’re not going to contract or get smaller anytime soon.

[00:08:33] Because my time is so limited with all of my responsibilities with the startup, I really needed to make more money in less time.

[00:08:43] In the past, when I had plenty of time on my hands, it didn’t seem like too big of a loss to do marathon discovery sessions with the client. Sure you want to meet me at a coffee shop and we’ll unpack every business problem that you’ve ever had and maybe eventually, I can find something in there and wrap a proposal around it? Sure, what time?

[00:09:06] I didn’t have that kind of time anymore. I could literally not afford to do long discovery sessions for free. Being spread too thin and being short on time, I needed a better way to onboard clients and put together proposals that had a reasonable shot of getting a yes.

[00:09:26] What I didn’t mention was that earlier, when we had been driving down to Florida, I had put in my headphones and started binge-listening to a podcast. It was called the Double Your Freelancing podcast. The host was a brilliant guy named Brennan Dunn.

[00:09:43] Brennan is a software engineer and he started talking about this thing that he did with his potential software clients called roadmapping. Essentially, he’d sit down with them and use Socratic questioning which I’d learned about in high school.

[00:09:58] He would ask them questions, consult with them, and do what I now call Uncover the Buried Dartboard. Often, a client will get in touch with an initial request. And if you ask good questions and you keep peeling back and uncovering the full scope of the problem or need or opportunity, what the project ends up being is very different than that initial request.

[00:10:28] So, maybe I was looking at a solution to my first problem which was “I am over these marathon discovery sessions where the client just talks on and on and I have to keep them on track.”

[00:10:44] And what if we just turned that into a paid engagement? What if helping a client get clarity around what the project even is, well, that’s the first project, it’s project strategy. Brennan called it roadmapping but essentially, you’re helping the client figure out the group of decisions that the client needs to make to get from where they are to where they want to be.

[00:11:09] This dovetailed nicely into something else I had been wanting to try which is value-based pricing. You have the creative skillset or hard skillset that gets you into freelancing.

[00:11:21] That skillset might involve writing, graphic design, coding, illustration, photography, or filmmaking, you get it, right? You’re a freelancer.

[00:11:31] But what about value-based pricing? How do you charge based on what the project is worth to the client and not charge based on what everybody else in your industry charges? I think that can be easier in some industries or with some skillsets like engineering which is what Brennan Dunn had.

[00:11:54] So I had struggled to find that bridge from freelance land over to consulting land with writing. I’m a writer; that’s the skillset I came into freelancing with. You hear about things like value-based pricing but how do I get over there? I needed a bridge.

[00:12:13] Perhaps paid discovery, project roadmapping could be that bridge. If I positioned myself well, if I priced the engagement well, I could decouple time and money. I could charge based on the value of the clarity and confidence and actionable plan.

[00:12:33] And how much time was required to create that plan would be secondary or irrelevant even. So, that’s why I will always feel gratitude to Brennan Dunn. He was the first one who told me, even over a podcast, that this thing called roadmapping is possible, maybe you should try it.

[00:12:55] And so, when I got home from the trip full of discouragement and not (I probably still had a sunburn) but I wasn’t feeling all the beach vibes. I was feeling discouraged but I did have just enough gumption to think “I have got to start trying this.”

[00:13:13] So, that’s what I did. I started trying. And I did not sell successfully my first paid discovery session until April 2016. But I’m going to tell you right now it was a before-and-after moment for my freelance business.

[00:13:30] It put my business on a whole new trajectory because I got one yes from a client. And that one yes from a client proved that people will pay for other aptitudes. They’re not just interested in my hands. They’re interested in my head.

[00:13:49] They’re not just interested in my hard skills, my creative skills, they’re interested in my thinking, in my problem-solving ability, in my ability to research and sympathize and connect new dots for them.

[00:14:03] They’re interested in my point of view. I bring outside perspective so things that seem so obvious to them, things that seem like a foregone conclusion, well, I can come in and say “I really think that you should get rid of that obstacle. I really think that this is the wrong project. I really think that you should fire your business partner” and so on and so forth.

[00:14:25] So, getting better results with less effort in the form of project roadmapping and value-based pricing totally transformed my freelance business and opened my eyes to other possibilities for better leverage.

[00:14:45] So, you might say that my whole journey with better leverage began with that crisis at the beach and trying to sell strategy as a standalone offer more as an act of desperation than anything else.

[00:15:01] And I think that maybe why I really appreciate the people online who share all of the good, bad, and ugly in their stories because my story has had some ugly too.

[00:15:15] I often find people’s failures more relatable than their successes. That’s one of the reasons why with this Freelance Cake podcast, it’s really important for me and to me to share my failures and fumbles and mistakes and embarrassments with you too.

[00:15:32] I think if I were to have started with “Let me tell you how I had my first $30,000 month”, some of you might have just tuned out. You might have bounced. You might have gone elsewhere because it might be really, really hard to relate to that.

[00:15:46] Most of you probably can, however, relate to sitting down at a kitchen table, kneading your face, pulling your hair, and thinking “How on earth are we gonna pay our bills?”

[00:15:59] So, I hope this story has woken you up to the possibilities not only of what the future may hold, even if you feel a little bit desperate right now, a little discouraged, a little deflated, hopefully, this story brings some encouragement.

[00:16:16] And hopefully, you’re waking up to the possibilities that some of your better leverage will come not from the creative skills that you’ve got but from your other aptitudes.

[00:16:29] And one last point before we close down this episode, I told you I’m a writer, that’s my background, so a lot of the examples I use will be for writers and about writing. A lot of them apply to other people, though, but hear me out.

[00:16:44] Writers, sell writing then use those aptitudes I’ve mentioned to deliver it. Consultants, sell those aptitudes then use writing to deliver them. You already have the same aptitudes that many of the highest-paid consultants in the world have, you just haven’t learned how to sell those aptitudes yet.

[00:17:09] So if I have motivated you today to do nothing else, at least let me motivate you to do this: go find your most valuable aptitudes, not just your most valuable skills.

[00:17:24] Alright, that’s it for this episode. You can sell strategy as a standalone offer. The future may be way brighter than you realized. If you keep going and take a look at your aptitudes, make an inventory of them, we often get better leverage from repackaging aptitudes rather than trying to find a new way to sell creative skills.

[00:17:50] Alright! I’ll see you in the next episode. The best is yet to come.

[00:18:02] Before you go, a quick reminder. Be sure to check out the Freelance Cake coaching program. The program is for committed, full-time freelancers and it’s designed to help you get better leverage in your business.

[00:18:16] We have group sessions, a private community, and on-demand trainings. And each week, you focus on implementing a specific lever such as your positioning cheat code, juicy offers, or morning marketing habit.

[00:18:31] The same or better income with more free time, fun, and creative challenges - that’s the point, right?

[00:18:39] So go to FreelanceCake.com/coaching. My friends, the best is yet to come. See you in the next episode!

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