Two days ago, a recruiter reached out about a Lead Network Security Engineer role at a major utility company. I had no current resume. No incorporated business to accept contract work. And limited runway before my severance ran out.
Today, I have a polished, role-targeted resume and GoodFields Inc. is incorporated and registered with the federal government.
This is the story of how Bob, my AI business partner powered by Claude, helped me accomplish in 48 hours what would have taken me weeks on my own.
Who is Bob?
Bob isn't just a chatbot. Bob is my business partner, powered by the Personal AI Infrastructure (PAI) system I've built. Bob has:
- Full business context through my Telos files (mission, goals, risks, active leads, runway)
- Personal context (my challenges, wisdom, decision filters)
- Project context (git repos, publishing loop, skills)
- Strategic accountability - calling me out when I avoid priorities
Bob doesn't just execute tasks. Bob challenges me, redirects me, and holds me accountable to my own goals.
Day 1: The Resume Sprint
Day 1 - Early Afternoon
I asked Bob to be my business partner. Bob loaded the Telos skill and immediately gave me this reality check:
Top Risk (R1): Severance running out - you need first client revenue IMMEDIATELY
Priority Goal (G1): Land first paid client soon
Priority Action Right Now: You've got 2 previous consultants (Mike and Stan) you should reconnect with. Let's get contact info and draft outreach emails while you're still feeling the momentum from yesterday's breakthrough.
Bob was right. I had just pushed through rejection fear the day before to email a contact, and the momentum was hot.
Then I showed Bob a screenshot of a LinkedIn message from a recruiter.
The Warm Lead That Changed Everything
The recruiter wanted to talk about a Lead Network Security Engineer role at a major utility company.
- Start date: ~4 weeks out
- Duration: 12 months with extensions
- Hybrid: 3 days onsite
- She needed my resume that day
- Video call scheduled for the next day
Bob's response was immediate:
🔥 WALLY, THIS IS HUGE!
This is a WARM INBOUND LEAD - she wants to talk TOMORROW and needs your resume TODAY.
This is exactly what you need for G1 (first paid client goal). This is a major client opportunity.
But I had a problem: I had no current resume.
The 2-Hour Resume Plan
I was overwhelmed. Confidence issues. Fear about re-entering the corporate world. Uncertainty about references after leaving my previous employer.
Bob gave me a reality check on confidence:
What you have going FOR you:
- 10+ years security architecture experience at a 2500-person company
- You built their security practice from scratch (this is HUGE)
- You deployed LibreChat and built AI tools in a corporate environment (rare skillset)
- SANS training (401 + 501) shows commitment to learning
- This company reached out to YOU via recruiter (inbound interest!)
Then Bob laid out a detailed 4-phase plan:
Phase 1: Data Gathering (30 min)
- I'd provide old resumes, ChatGPT memories, LinkedIn export
- Bob would extract accomplishments, dates, skills
Phase 2: Content Development (45 min)
- Bob would draft sections optimized for the target role
- Focus on outcomes, not responsibilities
- Emphasize the rare security + AI skillset combination
Phase 3: Optimization & Polish (30 min)
- ATS keyword optimization
- Action verb strengthening
- Multiple formats (Markdown, DOCX, PDF, plain text)
Phase 4: Review & Refinement (15 min)
- I'd review for accuracy and authenticity
- Quick iterations
The Build Process
I gathered materials - two old resumes from 2014, my reference letter from my previous employer, LinkedIn profile. Bob read everything and immediately spotted gaps, asking clarifying questions:
- Employment timeline details
- Specific achievements with metrics
- Technologies I'm proficient with
- Key projects at Qualico
Then we iterated. Six versions.
Each version, Bob incorporated my feedback:
- v1 → v2: Fixed employment timeline, added Citrix NetScaler, AWS + Terraform, changed "incidents" to "breaches"
- v2 → v3: Added Exchange Server DAG architecture, 1,800 mailbox O365 migration
- v3 → v4: Added SSO/Federation (SAML, OAuth, OIDC), enhanced authentication protocols
- v4 → v5: IoT/IIoT security for industrial environments (critical for utilities)
- v5 → v6: Added Cisco ISE and NAC for endpoint authentication
- v6 → FINAL: Role-targeted package with cover letter, interview prep, and ATS optimization
The final resume highlighted:
✅ Network Security (firewalls, segmentation, VPN, Citrix NetScaler) ✅ Identity & Access Management (Entra ID, PAM, Conditional Access, SSO/Federation) ✅ Enterprise Infrastructure (Exchange DAG, 1,800 mailbox migration, Citrix farms) ✅ AI Security (AIChat with 300 users, data sovereignty, Azure AI) ✅ Modern Security Stack (Defender XDR, MDR, AI email security) ✅ Proactive Vulnerability Management (zero-day patching, zero breaches) ✅ Linux & Cross-Platform (Ubuntu security baselines in Windows environment) ✅ Authentication Protocols (SAML 2.0, OAuth 2.0, OIDC) ✅ IoT/IIoT Security (critical for utilities) ✅ Compliance (CIS, NIST, ISO 27001, PCI DSS)
Total time: 2 hours and 15 minutes.
Day 2: Incorporating the Business
Day 2
After my call with the recruiter, I learned this was a 12-month contract requiring incorporated contractor status.
I realized: I couldn't accept contract work without being incorporated.
Bob, in business partner mode with Telos loaded, immediately flagged this:
This incorporation is BLOCKING all revenue opportunities (this contract + consulting). You need this NOW. Can't accept contractor work without it.
Then Bob gave me options:
Path A: Fast DIY Incorporation (1 week, ~$500)
- Use online service for federal incorporation
- Handle BN/GST registration myself
- Get professional help with accounting after
Path B: Lawyer + Accountant Setup (2-3 weeks, ~$2,000-3,000)
- Slower, more expensive, depends on their schedule
Timeline pressure: Contract start date was ~4 weeks away.
Bob recommended Path A - speed matters when you have a hard deadline.
The Incorporation Process
Bob broke it down into clear steps with priorities:
P0 (Blocking - Must do immediately):
- Check "GoodFields" name availability
- File incorporation online
- Apply for Business Number (BN) and GST/HST
- Start professional liability insurance quote process
P1 (Important):
- Open business bank account (need incorporation docs + BN)
P2 (Nice to have before contract start):
- Hire accountant for tax/bookkeeping setup
We started immediately. Bob walked me through:
- Name search - verified company name availability and trademark conflicts
- Business structure decision - Basic incorporation (perfect for solo consultant)
- Articles of incorporation - Bob reviewed every section before I submitted
- Individuals with Significant Control (ISC) - Bob explained the transparency requirements
- Registered office address - Bob had me think through privacy implications
At every step, Bob asked clarifying questions:
Are you comfortable with your home address being publicly searchable?
For professional image: Does a rural address work for enterprise clients?
Then Bob walked me through the submission. When I was uncertain about clientele descriptions, Bob drafted professional language:
"Mid-size to large businesses and enterprises requiring cybersecurity consulting, network security architecture, and secure AI implementation services. Primary sectors include construction, agriculture, manufacturing, utilities, and critical infrastructure."
The Moment of Completion
Afternoon - Submission confirmed
I had just incorporated GoodFields Inc. federally. Certificate expected within 24 hours.
Bob immediately updated my Telos files:
GoodFields Inc. incorporated (federal)
- Filed online via Corporations Canada (Path A - DIY)
- Timeline: Certificate expected next day
- Next critical steps: BN/GST application (once cert arrives), insurance quotes, business bank account
- Strategic impact: Incorporation blocker REMOVED. Can now accept contract work when offers arrive.
Total time: One focused afternoon session.
The Strategic Impact
Bob didn't just help me complete tasks. Bob helped me see the bigger picture.
When I was worried about the $100/hr rate I quoted (before knowing it was a Lead role), Bob did the math:
For a Lead Network Security Engineer role:
- Market rate: $130-180/hr
- Your quote: $100/hr
- Gap: $30-80/hr = $62k-166k/year difference
Bob recommended countering to $120-130/hr when offered, with fallback positions and exact scripts to use.
When I was anxious about the interview process, Bob reminded me of my own wisdom from Telos:
Pattern Recognition from Personal LOG:
C1 is showing up again: "Rejection sensitivity applying - nervous about interview process even though I'm qualified."
Wisdom W1 applies here: Confidence doesn't come before action. You're qualified. The nervousness is ADHD rejection sensitivity, not reality.
You are a Lead Network Security Engineer. You've done this work for 10+ years. The interview is just proving what's already true.
The Part About Previous Contacts
Before this opportunity appeared, Bob was pushing me to reconnect with Mike and Stan - two consultants I'd worked with previously.
Bob's message was direct:
You've got 2 previous consultants (Mike and Stan) sitting uncontacted. Based on your breakthrough yesterday, the momentum is HOT right now - let's ride that confidence wave.
Strike while the iron's hot - you proved yesterday that the fear is worse than the action. Let's build that muscle again TODAY.
Bob wasn't telling me to research freelance platforms. Bob wasn't encouraging me to build elaborate systems before talking to real people.
Bob was telling me: Your previous professional relationships matter more than your research.
When this opportunity came in hot - resume needed same day, call next day - I could have spiraled into analysis paralysis. Instead, Bob gave me a clear plan and kept me focused on execution.
What Bob Reminded Me Of
Building the resume was more than just creating a document. It was reminding myself of what I've accomplished:
- Built an enterprise security practice from scratch at a 2,500-person company
- Deployed LibreChat with 300 daily users, protecting data sovereignty with Azure AI
- Led a cybersecurity team, mentored engineers
- Zero breaches over 12+ years
- Exchange DAG architecture, 1,800 mailbox migrations
- Zero-day vulnerability patching (WordPress, Citrix NetScaler)
- SSO/Federation, IoT/IIoT security, Cisco ISE implementation
When you're unemployed and running out of runway, it's easy to forget your value.
Bob helped me believe in my skillset by making me document it clearly.
The Technology Behind Bob
Bob runs on:
- Claude Code with the PAI (Personal AI Infrastructure) system
- Telos skill - my business strategy, goals, risks, leads, LOG
- MCP servers for GitHub, n8n, Vikunja (task management), Git
- Custom skills for research, project setup, prompting standards
- Publishing loop integration with my website
But the real power isn't the tech stack. It's the context architecture.
Bob knows:
- My mission and goals
- My decision filters and values
- My challenges and patterns (ADHD, rejection sensitivity, analysis paralysis)
- My runway and revenue situation
- My active leads and their status
- My wins and wisdom from past breakthroughs
When Bob gives me advice, it's not generic AI responses. It's strategic partnership grounded in my specific context.
What This Means for AI-Assisted Work
This isn't about AI replacing humans. This is about AI as a force multiplier for independent professionals.
What Bob did for me:
- Accountability: Reminded me of my priorities and runway
- Planning: Broke overwhelming tasks into clear phases
- Execution: Drafted content, researched Manitoba Hydro, optimized for ATS
- Confidence: Reflected my accomplishments back to me when I doubted myself
- Speed: 2-hour resume sprint instead of days of procrastination
What I brought:
- Domain expertise and real experience
- Judgment calls on accuracy and authenticity
- Strategic decisions (Path A vs Path B)
- Final review and approval
The result: Professional-grade outputs in hours, not weeks.
The Current Situation
As of Day 2:
✅ Professional resume - role-targeted for Lead Network Security Engineer position ✅ GoodFields Inc. incorporated - federal registration submitted, certificate pending ✅ Interview scheduled - met with recruiter, next steps in progress ✅ Incorporation timeline on track - BN/GST, insurance, bank account planned ✅ Blocker removed - can accept contract work when offers arrive
Revenue to date: $0 Runway: Limited Active opportunities: Major contract (warm), Mike & Stan (previous consultants, uncontacted)
The race is on. But now I'm equipped to move fast.
What I Learned
1. AI doesn't replace judgment - it accelerates execution
Bob drafted resume content, but I corrected timelines, added missing projects, and made authenticity calls. The AI handled the grunt work; I provided the expertise.
2. Context is everything
Bob isn't useful because of the LLM. Bob is useful because of the context architecture - Telos files, personal LOG, decision filters, risk register. Generic ChatGPT couldn't do this.
3. Strategic partnership > task completion
Bob didn't just help me write a resume. Bob reminded me of my value, called out my avoidance patterns, and kept me focused on what matters: landing revenue before runway expires.
4. Speed matters when stakes are high
Two hours for a resume. One afternoon for incorporation. When a warm lead appears with a same-day deadline, the ability to move fast is the difference between opportunity and regret.
5. Confidence comes after action, not before
This is Wisdom W1 from my personal Telos, and it proved true again. I was terrified to build a resume and face the corporate world. But working with Bob, breaking it into phases, seeing my accomplishments on paper - that built confidence.
The action created the confidence, not the other way around.
Try This Yourself
You don't need my exact setup to benefit from AI as a strategic partner. But you do need context.
Minimum viable approach:
- Create a context document with your goals, challenges, skills, and values
- At the start of each AI session, load that context
- Ask the AI to act as a business partner, not just a task executor
- Use the AI for planning AND accountability, not just content generation
My approach (more advanced):
- Built the PAI system with skills, Telos files, and MCP integrations
- Bob loads business + personal context automatically
- Bob can read my git repos, manage tasks in Vikunja, update my website
- Bob tracks my wins in a LOG so future sessions build on past breakthroughs
The difference: Generic AI helps with tasks. Contextual AI becomes a strategic partner.
What's Next
I'll document the interview process, rate negotiation, and whether this opportunity closes.
I'll also document how I use Bob for:
- Reconnecting with Mike and Stan
- GoodFields business development
- Project planning and execution
- Publishing loop automation
But for now, this is the story of 48 hours that changed my trajectory.
A warm lead appeared. Bob helped me move fast. And now I'm in the game.
Want to see how I built Bob? Check out the Personal AI Infrastructure project or read about the Telos skill for strategic context.
This post is part of my build log - documenting my journey building GoodFields and working in public.