The $0-$1K/Day Case Study: Day 18

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What I did today

So today was really crappy. It was quite shit actually.

On the other hand, today was a great day.

Here’s what I mean.

If you look at the earnings down below, today was by far the best day I’ve had. I made more than $1,500 today, which is on pace to make more than $500K in a year.

But, today was actually one of the saddest days I’ve had in a long time. Here’s why:

  • I woke up at 7:30am after 3 hours of sleep and was absolutely gassed
  • I woke up to a note from my biggest clients, who pointed out that there was a big error in a deliverable I made for them
  • I had three coffees (larges from Starbucks) before 12noon
  • It’s now 9pm and I have ~4–5 hours of work left today that I haven’t even gotten to yet, part of which includes fixing some of the errors in my prior clients
  • I still have a ton of debt
  • I am at the mercy of my reviews, which very well could be crap based on how projects are going
  • I’m stressed and can feel an ulcer coming on

So, in other words, today was an extremely successful day but all I want is for it to stop. I don’t want to keep doing this. My amazing girlfriend called me out on this today, and she was right.

I think today has been a great instruction in a Warren Buffett quote that I absolutely love: “If you don’t find a way to make money while you sleep, you will work until you die.”

I love that quote. It’s on a list of quotes I read every morning. I read it every as a reminder of what I should be doing and where I should be going.

But my take away from today is, even though I’m making progress, I’m not practicing what I preach.

I need to generate money in a way that is repeatable, scalable, and doesn’t kill me. I also need to get out of debt.

So, here’s my new plan:

  • I don’t take any job that is less than $1,000
  • I only work on ~2–3 projects at a time
  • I need to start building “passive income”

Regarding passive income, I have a couple things in motion on that front. However, I need to start building out more.

I’d love to live in a world where I have ~25 affiliate websites, each generating substantial revenue. I’d do some writing, but most of that would be outsourced to fantastic writers. I’d have a team that works for me that does keyword research and finds the topics to write on. I’d have webmasters that do SEO outreach for me and get me backlinks.

That feels like a fricken blast! In fact, that feels like the kind of business I can’t wait to be a part of. I’d use that income to buy real estate.

I’m working on getting there. In fact, I’ll be there before long.

But until I am there, I need to keep pushing!

What I made today

Job: $128

UpWork: $122.50

KDP: $0

Catalant: $1,250

Interview Coaching: $0

Medium: $2.00

Total: $1,502.50

Today’s pro-rated amount of monthly expenses

Expenses: $212

Today’s Income

Made: $1290.50

This is a new record, but man it doesn’t feel like it

My plan for tomorrow

Tomorrow should, as I said yesterday, hopefully be easier. However, I really do hope it ends up being an easier day! I was wrong yesterday about today.

But, I don’t have any crazy meetings scheduled and that helps a lot. I have some catch up work for some low-ticket customers (<$1,000) that I can’t wait to be done with and never hear from again!

In the interim, I’m going to continue pushing along with some of the bigger projects I have.

Past Pieces

Day 1

Day 2:

Day 3:

Day 4:

Day 5

Day 6

Day 7

Day 8

Day 9

Day 10

Day 11

Day 12

Day 13

Day 14

Day 15

Day 16

About the Author & The $0-$1K/Day Case Study

Dean’s goal is to create $1,000/day in passive income through entrepreneurship. Too many people write “success porn” that skates over the struggles many face in entrepreneurship

The reason he writes brief posts here every day on Medium is to share his progress and his struggles. You get the unvarnished truth: what worked, what didn’t, and how much farther is there to go.

The hope is that this series of posts will inspire someone else out there to make their entrepreneurship dreams happen.

Dean Woods is currently a VC-backed startup executive by day and a bootstrapped micro-startup CEO by night. Prior to working in startups, Dean was at Boston Consulting Group. Dean graduated with honors from The Wharton School.

What I did yesterday to make $10K a day at 30

The current phase of the plan

Wake up & sleep:


Stress levels


My Day Job

Investment real estate

My Actual Business

Side Consulting

$10K/day website


Rescue Time Daily Screenshot

Today’s pro-rated amount of monthly & yearly expenses

Today’s Income (pre-tax)

My plan for tomorrow

Dean Woods

Dean Woods

Dean’s goal is to create $10,000/day in passive income through entrepreneurship. Too many people write “success porn” that skates over the struggles many face in entrepreneurship. His goal is to create something real that highlights the lack of sleep, disappointment from family, and setbacks you really face in entrepreneurship. The hope is that $10K a day swill inspire someone else out there to make their entrepreneurship dreams happen. Dean Woods is side hustling and working a full time job to kickstart his entrepreneurial path. Prior to this life, Dean was a management consultant. Dean graduated with honors from The Wharton School.

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