I’ve been fired three times. Each time, I had to rebuild from zero. The last time—July 2020, mid-pandemic—I was determined to do it differently. No more scrambling for another cubicle. No more begging for permission to work remotely.
I gave myself 90 days to hit $10,000/month in remote income. I missed the deadline by 11 days. On day 101, I deposited my first $10,847.
That was 2020. It’s 2026 now, and the playbook has changed. AI isn’t coming for your job—it’s coming for your excuses. The people who figure out how to work with AI instead of against it are replacing six-figure salaries in months, not years.
This is the exact 90-day roadmap I would use if I started from zero today. No courses to buy. No gurus to follow. Just the specific steps, tools, and daily actions that actually work in 2026.
The 2026 Reality Check
Let’s address the elephant in the room: AI has changed everything.
In 2020, I spent 40 hours a week writing blog posts, managing spreadsheets, and sending cold emails. In 2026, I do the same work in 10-15 hours because I have an AI assistant running on my Mac Mini handling the repetitive tasks.
I use Claude for deep research, writing, and analysis. I use OpenClaw (an open-source AI agent I run locally) to automate my email, manage my calendar, draft proposals, and handle client follow-ups. Together, they’re like having a $100,000/year employee who works 24/7 and never calls in sick.
This isn’t about replacing humans. It’s about replacing the 80% of your work that’s administrative, repetitive, and drains your energy—so you can focus on the 20% that actually makes money.
Here’s how to do it in 90 days.
Days 1-30: Foundation & First Dollars
Week 1: Inventory Your Skills (Days 1-7)
Before you can sell anything, you need to know what you’re selling. Most people skip this step and wonder why they’re flailing.
Action: Create a “Skills Inventory” document. List every job you’ve had, every task you’ve performed, every tool you’ve used. Don’t filter. Include:
- Hard skills (Excel, writing, coding, design, project management)
- Soft skills (communication, negotiation, problem-solving)
- Industry knowledge (healthcare, finance, SaaS, e-commerce)
- Tools you’ve mastered (Salesforce, HubSpot, Photoshop, Notion)
AI Accelerant: Feed your resume and job descriptions into Claude. Ask: “Based on this experience, what 5 services could I sell remotely for $75-150/hour?” The answers will surprise you. I discovered I could charge $100/hour for something I thought was “just part of my job.”
Week 2: Pick Your First Offer (Days 8-14)
You don’t need ten income streams. You need one that works. The goal this month isn’t diversification—it’s validation.
The 2026 Sweet Spots:
- AI Implementation Consultant — Help small businesses integrate AI into their workflows. Every company wants this; almost none know how to do it. You don’t need to be an engineer. You need to be the translator between AI tools and business outcomes.
- Content Systems Operator — Businesses need content (blogs, social, email). You build the system: AI-assisted research, writing, scheduling, and analytics. You become the person who “just handles it.”
- Remote Operations Manager — Virtual assistants are commodity. Operations managers who can build systems, hire contractors, and optimize processes command $5,000-10,000/month retainers.
- Specialized Freelance Writer — Not generic blog posts. Technical writing, case studies, white papers, or industry-specific content. AI can draft; you provide strategy, interviews, and polish.
Action: Pick ONE. Create a one-page service description. What do you do? Who is it for? What result do they get? What’s the price?
My first offer was simple: “I write email sequences for SaaS companies. $2,500 per sequence. 2-week turnaround.” That’s it. No website, no portfolio, no LLC.
Week 3: Build Your Minimum Viable Portfolio (Days 15-21)
You need proof you can deliver. But here’s the secret: you don’t need paid work to create proof.
The Portfolio Shortcut:
- Pick 3 dream clients in your target market (real companies you want to work with)
- Create a sample project for each—as if they hired you
- Document your process with screenshots, AI prompts, and deliverables
Example: If you’re offering AI implementation consulting, pick a local dentist, a real estate agency, and an e-commerce store. Create a proposal showing exactly how you’d save them 10 hours/week using AI tools. Do the research. Build the demo. Show your work.
AI Accelerant: Use Claude to research each industry, draft the proposals, and create the sample deliverables. What used to take 20 hours takes 4.
Week 4: Land Your First 3 Clients (Days 22-30)
This is where most people fail. They build. They plan. They perfect. They never sell.
The 2026 Outreach Method:
Forget Upwork. Forget cold email blasts. The method that works in 2026 is warm personalized video outreach.
The Process:
- Find 50 businesses that fit your ideal client profile (LinkedIn Sales Navigator, Apollo.io, or just Google)
- Research each one for 5 minutes: What do they do? What’s their recent news? Where’s the pain point you can solve?
- Record a 60-second personalized video using Loom or Vidyard
- Send it via LinkedIn DM or email with a specific, low-friction offer
The Script:
“Hi [Name], I was looking at [Company]’s [specific thing] and noticed [specific opportunity or problem]. I help [type of company] [specific result] using [your method]. I made a 2-minute video showing exactly how I’d approach this for you. Worth a quick look?”
Send 10 per day. That’s 300 outreach attempts in 30 days. With a 5% response rate (conservative), that’s 15 conversations. Close 3 at $1,000-2,000 each. Month one: $3,000-6,000.
AI Accelerant: I use OpenClaw to research prospects, draft personalized opening lines, and schedule follow-ups. What used to take 2 hours per day takes 30 minutes.
Days 31-60: Scale to $5K/Month
Week 5-6: Systematize Your Delivery (Days 31-42)
You have clients. Now the real work begins: delivering excellent results without working 80-hour weeks.
The AI-First Workflow:
For every project, I build a system:
- Research Phase: Claude summarizes industry reports, competitor analysis, and client materials in minutes, not hours
- Creation Phase: AI generates first drafts, outlines, and prototypes. I edit, refine, and add strategic insight
- Review Phase: AI checks for errors, suggests improvements, and ensures consistency
- Delivery Phase: Automated client updates, file organization, and follow-up scheduling via OpenClaw
This isn’t cutting corners. It’s leveraging tools to deliver better results faster. My clients don’t care if AI helped draft the report. They care that the report is excellent and delivered on time.
Week 7: Raise Your Prices (Days 43-49)
Here’s a secret: pricing is arbitrary until you prove value. Most freelancers undercharge for years because they’re scared.
The Pricing Ladder:
- First 3 clients: Charge enough to get yeses ($500-1,500/project)
- Next 3 clients: Raise 50% ($750-2,250/project)
- Clients 7+: Raise to market rate ($2,000-5,000/project)
If you’re not getting pushback on price, you’re too cheap. I knew I was priced right when 30% of prospects said “that’s more than we budgeted.” The other 70% paid without blinking.
Week 8: Add Predictable Revenue (Days 50-60)
Project work is feast or famine. You need recurring revenue to hit $10K consistently.
The Retainer Transition:
Take your best project client and propose a monthly retainer:
“Instead of $2,500 per email sequence, what if I handled all your email marketing for $3,500/month? That’s 2 sequences plus ongoing optimization, A/B testing, and monthly reporting. You get consistent output and predictable costs. I get to go deeper on strategy. Win-win.”
Target: 2-3 retainer clients at $2,500-4,000/month by day 60.
Days 61-90: Hit $10K and Build Systems
Week 9-10: Productize Your Service (Days 61-74)
You’ve proven demand. Now make it scalable.
Productized Service = Specific Result + Fixed Price + Defined Timeline
Instead of “I do email marketing,” it’s:
“The Email Engine: A complete email automation system for SaaS companies. 6 automated sequences, 24 emails, set up in 14 days. $5,000 flat fee.”
Benefits:
- No scope creep
- No custom proposals
- Can delegate parts to contractors
- Easier to sell (clear outcome)
I productized my service on day 67. Revenue jumped 40% the next month because I could close faster and deliver faster.
Week 11: Build Your AI Team (Days 75-81)
You’re not just building income. You’re building a system that generates income. In 2026, that system includes AI agents.
My Current Setup:
- Claude: Research, writing, analysis, strategy, client communication drafts
- OpenClaw: Email management, calendar scheduling, task tracking, content distribution, research automation
- Make/Zapier: Workflow automation between tools
- Notion AI: Project management, documentation, brainstorming
This isn’t science fiction. These are tools available today, many free or low-cost. The freelancers and consultants who master AI assistance will replace those who don’t. It’s that simple.
Week 12: Optimize for $10K Months (Days 82-90)
By day 90, your goal is:
- 2-3 retainer clients ($5,000-8,000/month)
- 1-2 project clients per month ($2,000-5,000)
- Systems that let you deliver in 20-30 hours/week
If you’re at $6,000-7,000 on day 90, you’re on track. Push hard on outreach, raise prices on new clients, and add one more retainer. You’ll hit $10K by day 100-110.
The Exact Daily Schedule
Here’s what my days looked like during the 90-day sprint:
6:00 AM – 8:00 AM: Deep Work
Client delivery. Writing, strategy, calls. The money-making work. No email, no Slack.
8:00 AM – 9:00 AM: AI-Assisted Admin
Check OpenClaw’s overnight work. Review AI-drafted emails. Send follow-ups. Plan the day.
9:00 AM – 12:00 PM: Outreach & Sales
10 personalized video outreaches. Follow-ups. Sales calls. This is non-negotiable until you have $10K/month locked in.
12:00 PM – 1:00 PM: Break
Eat. Walk. Clear your head.
1:00 PM – 4:00 PM: Client Work & Systems
Delivery, client calls, building SOPs and AI prompts.
4:00 PM – 5:00 PM: Learning & Optimization
Read industry news. Test new AI tools. Refine your systems.
Total: 10-11 hours/day, 6 days/week for 90 days. Then you have a $10K/month business that runs in 20 hours/week.
The Mindset That Actually Works
I’ve given you the tactics. Here’s what matters more:
1. Speed beats perfection. I sent terrible outreach videos. I took on projects I wasn’t fully qualified for. I raised prices before I felt “ready.” Action creates clarity. Planning creates procrastination.
2. AI is a multiplier, not a replacement. I still work hard. I still think deeply. But AI lets me do 3x the work in the same time. The people who treat AI like a shortcut get caught. The people who treat it like leverage win.
3. The first $1,000 is harder than the next $9,000. Getting started is brutal. Rejection stings. Imposter syndrome screams. Push through. By client #3, you’ll have confidence. By client #10, you’ll have a business.
4. Your network is your net worth. Every client came from a relationship. Former colleagues. LinkedIn connections. People I helped for free. Be generous. Stay visible. It compounds.
The 2026 Advantage
Here’s why this works better now than in 2020:
- Remote work is normalized. Companies expect to hire remotely. No more explaining why you’re not in an office.
- AI handles the grunt work. What used to take 40 hours takes 15. You can serve more clients or work less.
- Global talent pool. You’re competing with the world, yes. But you’re also selling to the world. Price in USD. Live somewhere cheap. Geographic arbitrage is real.
- Information is free. Every skill you need—sales, marketing, delivery—you can learn free on YouTube, in documentation, or by asking AI.
The barriers are gone. The only thing standing between you and $10K/month is 90 days of focused execution.
Your Next Step
Don’t bookmark this and come back later. Open a document right now.
Title it: “90-Day Plan”
Write down:
- Your top 3 skills
- The one service you’ll offer
- 10 companies you’ll reach out to this week
- The AI tools you’ll use (Claude, OpenClaw, etc.)
Then close this browser tab and take the first action.
Day 90 will come whether you start or not. The question is: Where will you be?
Related Reading:
- How to Become a Freelancer
- Essential Advice for Making Money Remotely
- How I Earned $10,000 on Upwork
- The Simple Plan to Become a Digital Nomad
Questions? Hit me on Twitter or email. I read every message.