The Day I Lost $5,000 is the Day My Success Finally Began…

Jul 29, 2019

With six children to feed… and not income… and the only hope of income resting on the only proposal I’d sent out earlier in the week… I was a nervous wreck. 


It was November 2005 and I’d been trying to find clients since August. So far… zip, nada, donuts. 

We lived up the canyon, just outside of Helena, MT. Our rent was $950 a month and we didn’t have a car payment. We lived pretty fugal. But the reality was, the electric company, WalMart, comcast, and other service providers wanted money to use their services and eat their food. 

I needed that contract. 

I remember exactly where I was standing the day the phone rang. “Joshua, we’d like to put you on retainer for $5,000 a month. Do you think you can write one promotion for us each month?” 

$5,000????!!!! I just about passed out. It was more than I hoped for… more than enough to keep us going. 

“Yes, I think I can do that.” I said as calmly as I could. 

Six weeks later, I wasn’t so calm. They assigned me to do a long-copy promo. I was now on draft three. They hated every word of it…. again. 

Sitting at my computer, I was in a panic. I HAD to get this right. 

I started at the beginning on draft four and reworked the whole thing. 

Two days later the phone rang again, “Ummm, Joshua, we really appreciate what you’re trying to do, but we just don’t think your approach and style will work for us. You can keep the first retainer payment we gave you, but we need to terminate the contract. Thanks for trying.” 

Just like that, it was over. I was back to no income, 6 children to feed and $200,000 of debt to face every morning. 

It felt like the worst day of my life. I felt ashamed. I felt like a failure. 

I went into a tailspin for another six weeks. 

Finally, Margie sat down with me. 

“Joshua, why are you so depressed? You’ve got to pull out of this.” 

“I just don’t think I can do this writing thing. I tried my very best on those promos and they hated it… hated every word of it. I don’t have a college degree. Flippin’ burgers at McDonald’s won’t cover our expenses. I’ve got no qualifications so no one would hire me even if I could stomach a real job. I failed you. I’m so sorry.” 

“Joshua, will you do something for me? Will you spend some time researching how many technology companies there are in the United States? Then tell me what you find? OK?” 

In my misery I agreed. 

I spent a day digging around, reading, and researching. 

What I found and what Margie said to me changed my life forever. 

“What did you find out about tech companies today, honey?”

“Margie, you’re not going to believe this, but last year, there were 285,000 tech firms in the US. And that doesn’t include hardware companies. That’s just mostly software! All told, there are close to a million different tech companies.” 

I never imagined there were so many. It was exciting to me, since that was my niche. 

“Now, Joshua, even if you’re the worst writer in the world… and you’re not, you just weren’t a good fit for those other guys… but even if you were, don’t you think that out of almost a million companies, someone, somewhere would hire you? 

And, even if they only pay you half your fee and you learn more about what you’re doing wrong, eventually you’ll get better and you’ll make some money along the way. So, isn’t it time to contact some of them? ” 

She was right. I felt it deep in bones. She was right (always is! LOL). 

I realized that day that there was virtually an unlimited number of companies that I could approach. Eventually I’d figure it out. 

And I did. 

I got back to work and went after my dreams of living the writer’s life. 

That was January of 2006. 

By April of 2006, I was writing for Sony, Corel, Google, Toshiba, and Verizon. Before the end of the month, I’d put more than $90,000 in the bank in writing fees. 

I have seen this pattern over and over again as I have worked with thousands of writers. 

It has taught me that our greatest opportunities lie in rejection. Success is a fierce taskmaster. She ruthlessly guards her gates and only allows the truly committed and determined inside her walls. 

You will face rejection. Maybe you’re facing rejection right now. Maybe you’re like I was and still licking your wounds. 

No matter where you’re at, you can do three specific things about rejection.

First, embrace the pain, fear and frustration. 

Rejection hurts. It is embarrassing. It leaves wounds and costs you money. 

Pretending that it doesn’t is lame. You’re human. Go ahead and sit with the pain and fear and disappointment and everything else that comes up. 

You can’t really move on until you do, so get it over with. 

Second, face the facts. 

You were rejected for a reason. Get comfortable dealing with reality. Most likely you didn’t do something you should have done. You dropped the ball. You weren’t totally qualified. 

Whatever it is, it is not a judgement… it is feedback. It’s the schoolmaster of life teaching you. You can pout about it… or learn from it. 

Take the feedback and use it to fuel your improvements. 

In my case, my copy really did stink and I was being pig-headed about doing it my way vs their way. They gave me samples and told me to replicate them, but with new “big ideas” and stories. 

I was sure I could do a better job and continued to force my way on them. It wasn’t a better job and they didn’t like the approach. 

Lesson learned… polish my writing skills and cater to the guy paying you. 

Another aspect of facing the facts: I had to realize – and Margie helped me do this – that this was just one client, one opinion, out of close to a million potential clients. 

As long I was determined to not give up, eventually I would make it. That was a fact. In my depression I failed to see it. 

Researching the reality of the situation is what opened my eyes. 

Finally, get back in the saddle… Success is imminent. 

When you’re working outside in the garden and get a few blisters, the body responds by growing tougher skin. Calluses are tougher than regular skin and allows us to work harder, longer, and more effective than before. 

Rejection can, if you let it, make you stronger. But the only way to let that happen is to jump right back in. 

Lost a contract? Had a proposal rejected? Failed to hit a goal? 

It’s part of life. Jump right back in. 

It is in the ashes of our defeats that we find the greatest victories.


Joshua T. Boswell

Founder & CEO of Copywriter Marketer

He’s been the personal copywriter and business trainer for startup founders, authors, 
public speakers, entrepreneurs and over 5,000 clients around the world. His techniques have been show to dramatically improve career success, work quality, copywriting tactics, marketing skills, income and even overall life and relationships! Now Joshua Boswell can be YOUR virtual coach!

How To Launch A Money-Making Freelance Writing Business in 30 Days or Less!

Discover the secrets about making money with freelance writing…. without major risk or any writing background!

Register now for this special training. I show you exactly how to launch your freelance writing business.

Don’t reinvent the wheel.

Start here.


Expert Strategies

Join thousands of subscribers! Get 4 new breakthroughs every week on how to write better copy, market your services, develop a winning mindset and live the writer’s life!

Help & Support

Questions, comments or concerns? Our team is here for you no matter what.

Review our FAQ's and documentation for instant support or send us a message.

Share This