Dear Fellow Professional,
If you’re reading this, you’re probably where I was 18 months ago: successful in your field, respected for your expertise, but increasingly worried that you’re falling behind.
You’ve heard about AI. You know it matters. You’ve probably experimented with ChatGPT once or twice. Maybe you were impressed. Maybe you were disappointed. Maybe you just felt lost.
I get it. I was there too.
I’m writing this letter because I remember how isolating those early days felt. Everyone else seemed to either “get it” instantly or not care at all. I was somewhere in between—interested but uncertain, hopeful but skeptical, willing but overwhelmed.
What follows is what I wish someone had told me on Day 1. Not theoretical advice. Not hype about AI’s potential. Just practical wisdom from someone who’s been exactly where you are.
This is your roadmap for the first 100 days.
Week 1: Permission to Be a Beginner
What you’ll feel: Awkward. Uncertain. Maybe a little stupid.
You’ve been an expert in your field for decades. Suddenly, you’re fumbling with tools that 25-year-olds seem to use effortlessly. That’s uncomfortable.
Here’s what I learned: Everyone is a beginner with AI. The 25-year-olds are just better at hiding their uncertainty.
What to do this week:
Day 1-2: Just start
- Sign up for ChatGPT Plus ($20/month)
- Don’t overthink it
- Ask it three questions you’d normally Google
- Notice how it responds
That’s it. No courses. No tutorials. Just use it.
Day 3-5: Use it for real work
- Draft an email you need to write
- Summarize a long document
- Brainstorm ideas for a current project
- Ask it to explain something you don’t understand
Don’t worry about “doing it right.” There’s no right way yet.
Day 6-7: Reflect
- What worked? What didn’t?
- What surprised you?
- What seems useful? What seems overhyped?
My breakthrough moment: Day 4. I asked ChatGPT to analyze a client’s competitive landscape. Instead of spending two days on manual research, I had comprehensive analysis in 45 minutes. Not perfect—but 80% of the way there.
That’s when I realized: This isn’t about replacing my expertise. It’s about amplifying it.
Your mission this week: Give yourself permission to experiment without judgment. You’re learning. That’s supposed to feel awkward.
Week 2-4: Building Daily Practice
What you’ll feel: Alternating between excitement (when it works) and frustration (when it doesn’t).
This is normal. AI is powerful but inconsistent. Learning to work with that inconsistency is the skill.
What to do these weeks:
Build a prompt library: Every time you write a prompt that works well, save it. By end of month, you should have 15-20 reliable prompts for common tasks.
Mine included:
- “Analyze this data and identify three strategic insights I might miss”
- “Review this draft and suggest improvements to clarity and impact”
- “Generate five alternative approaches to [problem]. Explain trade-offs of each.”
- “What questions should I be asking about [situation] that I’m probably not asking?”
Use AI for everything you can:
- Meeting prep
- Email responses
- Research and analysis
- Brainstorming
- Document summaries
- First drafts of everything
Not because AI does these better than you. Because it does them faster, freeing your time for higher-value work.
Document what works: Keep a simple log:
- What task did you use AI for?
- How long did it take?
- How long would it have taken manually?
- What was the quality difference?
This log becomes proof of value. You’ll need it later.
My breakthrough moment: Week 3. I realized I was using AI wrong. I was asking it to “write” things. Better approach: ask it to help me think through things, then I do the writing.
That shift—from AI as writer to AI as thinking partner—changed everything.
Your mission these weeks: Build AI into your daily workflow. Make it habitual, not special.
Month 2: First Real Project
What you’ll feel: This is where doubt creeps in. You’re competent with basic usage, but not sure if you’re actually creating meaningful value.
What to do this month:
Choose a portfolio project: Something real and challenging. Not a practice exercise. Actual work that matters.
Criteria:
- Connects to your expertise
- Would normally take 15-20 hours
- Creates demonstrable value
- You can show to others
Examples from people I know:
- Competitive analysis normally taking 3 weeks, done in 5 days
- Client strategic brief normally taking 10 hours, done in 3
- Market research synthesis normally taking 40 hours, done in 12
Document your process:
- What AI tools did you use?
- What prompts worked best?
- Where did you add expertise that AI couldn’t provide?
- What was the final outcome?
This documentation matters. You’re not just creating output. You’re proving a new capability.
Test your work: Share it with someone whose judgment you trust. Ask:
- Is this as good as my normal work?
- Is it better in some ways?
- Where does it fall short?
Use feedback to refine.
My breakthrough moment: Month 2, Week 2. I completed a strategic analysis for a client that would normally take me 25 hours. Did it in 7 hours with AI. Client said it was the most thorough analysis they’d ever received.
That’s when I knew this wasn’t just efficiency. It was capability expansion.
Your mission this month: Build something you’re proud of. Something that proves to you (and potentially to others) what experience + AI can create.
Month 3: Strategic Application
What you’ll feel: Confidence building. You’re no longer a beginner. You’re developing a point of view about how AI enhances your specific expertise.
What to do this month:
Build two more portfolio projects: Each should push you slightly beyond your last project. More complex. More strategic. More demonstrative of expertise + AI.
Start making it visible:
- Update LinkedIn with AI capability
- Write one post about what you’ve learned
- Share a project (anonymized if needed) with your network
- Offer to present your approach to colleagues or peers
Not to brag. To signal capability. The market can’t value what it doesn’t see.
Identify your positioning: How does AI enhance what you specifically offer? What can you now do that you couldn’t before?
Mine was: “I help B2B companies develop marketing strategy using 25 years of expertise amplified by AI. You get strategic thinking that would cost $500K in agency fees for a fraction of the price—in days, not months.”
Yours will be different. But it should clearly connect your expertise to AI capability.
Test new value proposition:
- Update your LinkedIn headline
- Revise your website or professional materials
- Pitch one new opportunity using your enhanced capability
- See how market responds
My breakthrough moment: Month 3, Week 3. I presented at a conference about AI-enhanced marketing strategy. After the session, three people approached me with consulting inquiries. Two specifically said they wanted to work with someone who combined experience with AI capability.
That’s when I realized the market was ready for this. I just needed to position correctly.
Your mission this month: Make your capability visible and test how the market responds.
Day 91-100: Planning Your Next Phase
What you’ll feel: You’re no longer learning AI fundamentals. You’re applying them strategically. The question shifts from “Can I use AI?” to “How do I leverage this fully?”
What to do these final days:
Assess your progress: Look back at your documentation:
- How much time have you saved?
- What quality improvements have you achieved?
- What can you do now that you couldn’t 100 days ago?
- What value have you created?
Decide your path:
- Continue in current role with enhanced capability?
- Reposition for different opportunities?
- Raise rates or change pricing model?
- Pursue advisory or consulting work?
- Build new service offerings?
Set your next 100-day goals: What do you want to accomplish in the next phase?
- More advanced AI applications?
- Additional portfolio projects?
- Thought leadership platform?
- Client acquisition using new positioning?
Make one bold move: Based on what you’ve learned, take one significant action:
- Raise your rates
- Pitch a new type of client
- Apply for a stretch role
- Launch a new service
- Speak publicly about your capability
Something that wouldn’t have been possible or conceivable 100 days ago.
My breakthrough moment: Day 95. I raised my consulting rate from $200/hour to $400/hour. Worried I’d lose clients. Instead, signed two new clients at the new rate within a week. They specifically wanted AI-enhanced strategic capability.
Your mission these final days: Consolidate what you’ve learned and plan your next phase of growth.
What I Wish I’d Known
Looking back on those first 100 days, here’s what I wish someone had told me:
1. The learning curve is shorter than you think
I thought building AI competence would take six months. It took six weeks to reach productivity. Three months to reach proficiency.
Don’t let imagined timeline deter you. You’ll be productive faster than you expect.
2. Your expertise makes learning easier, not harder
I worried that my age would slow me down. The opposite was true. My domain expertise meant I immediately knew what to ask AI and how to evaluate its answers.
Young workers learn the tools faster. You learn the application faster. Application matters more.
3. Imperfect action beats perfect planning
I wasted two weeks researching “the best way to learn AI” before I started. That was wasted time.
Just start using it. You’ll learn more in two hours of application than two weeks of research.
4. Portfolio proof changes everything
Nobody cared that I “knew how to use ChatGPT.” Everyone cared when I showed them work I’d created with it.
Build proof early. Share it often.
5. The market is ready
I thought I’d need to educate clients about why AI-enhanced capability mattered. I was wrong. They already knew. They just couldn’t find professionals who offered it.
Your expertise + AI is more valuable than you think. And rarer.
6. This is beginning, not end
100 days doesn’t make you an expert. It makes you competent and confident. That’s enough to create significant value.
The learning continues. That’s the point.
The Honest Truth About Fears
Let me address the fears you probably have but maybe haven’t said out loud.
“I’m too old to learn this” I’m 54. I learned it. You can too. Age is not the barrier. Willingness is.
“What if I invest time and it doesn’t work out?” 80 hours over 100 days is minimal risk. The cost of not trying is higher than the cost of trying.
“What if AI makes my expertise obsolete?” AI makes expertise more valuable, not less. Your judgment is the scarce resource. AI amplifies it.
“What if I look stupid while learning?” Everyone looks stupid while learning. The ones who succeed are the ones who don’t let that stop them.
“What if it’s too late?” It’s not. AI went mainstream in late 2022. We’re all early. The advantage goes to people who move in months, not years.
Your First Step
100 days from now, you can be in completely different position. Or you can be exactly where you are today, wondering why you didn’t start.
The difference is one decision: start this week.
Not next month. Not after you finish your current project. Not when you have more time.
This week.
Here’s what to do:
Today:
- Sign up for ChatGPT Plus
- Ask it five questions about your current work
- Notice what happens
This Week:
- Use AI for three real work tasks
- Document what works
- Keep going
This Month:
- Build AI into daily workflow
- Start first portfolio project
- Share one thing you learn
This Quarter:
- Complete three portfolio projects
- Update professional materials
- Make capability visible
- Test market response
That’s it. That’s the path.
A Final Word
Learning AI at 45, 55, or 65 isn’t about keeping up. It’s about pulling ahead.
Your expertise is the foundation. AI is the multiplier. Together, they create value that neither alone can produce.
I’m not special. I didn’t have technical background or natural affinity for new tools. I just decided that the next 20 years of my career would be better than the last 20.
So can you.
100 days from now, you’ll wish you started today.
So start today.
I’m rooting for you.
— Andreas
Want guidance through your first 100 days?
Join The Experience Multiplier and transform your expertise with proven frameworks, expert support, and cohort accountability.
Next cohort starts February 2026. Limited to 25 professionals.
Learn more at experienceadvantage.ai/course
Your expertise took decades to build.
Your AI competence takes 100 days.
Both together? Unstoppable.
Start today.
