How Bootstrappers Can Explore All Possible Ways to Tackle a Challenge
As a bootstrapper, you’re constantly problem-solving. Whether it’s acquiring customers, scaling operations, or refining your product, you often face challenges with no clear solution.
Instead of getting stuck, ask yourself:
“What are all the possible ways I could tackle this?”
This question forces you to think creatively, expand your options, and avoid the trap of pursuing a single (and potentially suboptimal) solution.
In this guide, we’ll walk through a structured approach to brainstorm, evaluate, and choose the best way forward when faced with a startup challenge.
Step 1: Define Your Challenge Clearly
Before coming up with solutions, you need to make sure you’re solving the right problem. A vague challenge leads to vague solutions.
Ask Yourself:
✅ What is the core issue I’m facing?
✅ Why is this a problem for my business right now?
✅ What would success look like?
💡 Example Challenge:
🚀 “I need to acquire my first 50 customers without a marketing budget.”
Clearly defining the challenge keeps you focused on practical, relevant solutions.
Step 2: Brainstorm as Many Solutions as Possible
Once you’ve framed the problem, list every possible way to solve it—without filtering or judging ideas. Your goal is quantity over quality at this stage.
💡 Example Challenge: “How can I get my first 50 customers without spending money?”
Possible Solutions:
1️⃣ Leverage my personal and professional network.
2️⃣ Offer a free trial or freemium version to attract users.
3️⃣ Get featured in relevant communities (Reddit, Indie Hackers, Facebook groups).
4️⃣ Run a referral or ambassador program.
5️⃣ Create viral, shareable content related to my industry.
6️⃣ Cold email or cold DM potential users.
7️⃣ List my product on directories like Product Hunt or AppSumo.
8️⃣ Partner with influencers or micro-influencers in my niche.
9️⃣ Optimize for SEO to get free organic traffic.
🔟 Collaborate with another startup for cross-promotion.
The key here is to go wide first—even if some ideas seem impractical, list them anyway. Sometimes, the best solution is a combination of multiple ideas.
Step 3: Categorize and Prioritize Your Options
Now that you have a list of possible solutions, it’s time to organize them into categories and rank them based on impact and feasibility.
1️⃣ Categorize Your Ideas
Grouping your solutions into categories can help you see patterns and gaps. For example:
🟢 Organic Strategies: SEO, community engagement, blogging, word-of-mouth
🟠 Outbound Strategies: Cold outreach, partnerships, referral programs
🔵 Product-Led Strategies: Free trials, freemium model, viral loops
🟣 Media & PR Strategies: Podcast appearances, guest blogging, influencer marketing
2️⃣ Prioritize Using the ICE Framework
One way to decide which ideas to pursue first is by using the ICE Score:
- I (Impact): How effective will this solution be?
- C (Confidence): How sure am I that this will work?
- E (Ease): How easy is it to execute?
Score each idea from 1 to 10, then focus on the highest-scoring ones.
💡 Example (Getting First 50 Customers):
| Solution | Impact | Confidence | Ease | Total Score |
|---|---|---|---|---|
| Leverage my network | 8 | 9 | 10 | 27 |
| Cold outreach | 7 | 7 | 6 | 20 |
| SEO | 9 | 8 | 4 | 21 |
| Community engagement | 6 | 7 | 9 | 22 |
| Product Hunt launch | 9 | 7 | 5 | 21 |
From this, you can see that leveraging your network and engaging in communities are the quickest and most effective ways to start.
Step 4: Test a Few Solutions Simultaneously
Instead of committing to a single strategy, test 2-3 of the highest-scoring ideas at the same time.
✅ Set a time limit – Example: “I’ll test these for 30 days and evaluate results.”
✅ Define success metrics – Example: “I expect 10% of cold outreach emails to convert.”
✅ Track progress – Keep a simple Notion, Airtable, or Google Sheet to record what’s working.
💡 Example: If you’re trying to get early customers:
- Week 1: Reach out to 50 people in your network.
- Week 2: Post in 5 relevant communities and track engagement.
- Week 3: Send 100 cold emails with a unique offer.
By testing multiple solutions at once, you increase your chances of success while reducing risk.
Step 5: Evaluate, Double Down, or Pivot
After running small tests, analyze what’s working and double down on the most effective approach.
Ask Yourself:
✅ Which method brought the best results?
✅ What did I learn that I didn’t expect?
✅ Should I refine, pivot, or try another approach?
💡 Example Analysis (Getting First 50 Customers):
- Cold outreach: Sent 100 emails → 5 conversions (5% success rate).
- Community engagement: 3 Reddit posts → 50 website visits → 2 sign-ups.
- Personal network: 20 referrals → 7 sign-ups (35% success rate!).
📌 Takeaway: Your personal network was the most effective, so you should double down on that while refining cold outreach.
Why This Process Works for Bootstrappers
✅ Prevents Analysis Paralysis – Instead of overthinking, you generate many possible solutions.
✅ Encourages Creativity – You go beyond the obvious answers and find unique angles.
✅ Helps You Move Fast – Testing small experiments ensures you don’t waste months on the wrong approach.
✅ Minimizes Risk – You make decisions based on real results, not gut feelings.
🚀 Take Action Now
1️⃣ Write down your biggest current challenge.
2️⃣ List at least 10 possible ways to tackle it.
3️⃣ Categorize and prioritize your ideas.
4️⃣ Test 2-3 solutions in the next 30 days.
5️⃣ Evaluate, double down, or pivot based on real data.
The best entrepreneurs don’t just find solutions—they find the right solutions by exploring every possibility.
What challenge are you working on right now? Drop it in the comments, and let’s brainstorm together! 🚀💡
