The $0-$1K/Day Case Study: Day 15

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What I did today

Today was really not a good day in the freelancing consulting world. In fact, it was a really bad day.

I woke up to messages from a client who is super unhappy with the work I did for her. It’s an $800 contract, with three deliverables. She has approved the first two deliverables and paid me for them.

However, she decided that she is “unhappy with the progress for the money that’s been paid.”

This is frustrating because she’s had multiple opportunities in phone calls and messages we’ve exchanged to say that she doesn’t like the direction we’re headed in. She waited until after most of the work has been completed to ask for it to be redone.

So, now I’m in an interesting position: I can refuse to redo the work, but then she’ll leave a quite poor review. Or, I can redo the work and maybe still get a poor review, but I’ll also have to invest time into this and I don’t really have that time to invest.

I think I’m going to redo it, but I’m not very happy about it. I thought I had screened my clients well and that she wouldn’t be a bad client, but I think I need do a better job screening.

The other client is my big client that’s at $700/day. I had a deliverable due for them, and I think it was decent, but they want some changes. I need to make updates and turn in a fantastic deliverable to ensure that they continue to be happy with me. I strongly hope this project with them turns into many more projects!

So today is going to be about redoing work for client number one and making edits for client number two. Let’s hope we can move these into a better direction.

What I made today

Job: $128

UpWork: $0

KDP: $0

Catalant: $700

Interview Coaching: $0

Medium: $1.00

Total: $829

Today’s pro-rated amount of monthly expenses

Expenses: $212

Today’s Income

Made: $617

My plan for tomorrow

Tomorrow is also going to be a pretty busy day. I have a project for a client to help build out a pitch deck for them. The pitch deck is a $1,000 project so important that I get that one done and going in the right direction as well.

A past client of mine also reached out to me and introduced me to a friend of his that is looking for help with their pitch deck. My expectation is that would probably be another $1,000+ project so that would be super helpful as well.

I also have another project underway that is a lot of work for only $150, but it’s recurring $150 every week so I’m a big fan of it!

There’s another project where I think I have a decent chance of winning that is $2,750 total.

All in, I have ~$4,000 of projects in the hopper or I think are >75% chance of selling. We’ll see what happens, but I think the odds are decent over here!

If that turns out to be true, I can start putting some money towards paying down some debt!

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

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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