The $50K Question: How I Chose Between My Dream Job and Starting My Own Company

📝 By: David Chen📅 11/26/2025🔄 Updated: Invalid Date

Hey, I'm David Chen, and I'm about to share the hardest professional decision of my life: whether to quit my stable $95K engineering job to launch my own SaaS company or take a "dream" senior role at a hot startup that had been courting me for months.

Here's the backstory: After eight years at a mid-size tech company, I got laid off (yeah, the "restructuring" thing). During my job hunt, I interviewed everywhere—from big tech to startups. I landed three solid offers, including one that made me literally scream when I got the call: Senior Engineering Manager at a fast-growing fintech unicorn, complete with a corner office, big salary, and stock options that could make me wealthy if the company IPO'd.

But then there was the other path: I'd been building this side project for two years (a niche project management 🔧 tool for creative agencies), and it had ✅ finally started gaining traction. I'd hit $8K in monthly recurring revenue, had 50 paying customers, and three agencies offered to be beta testers. I could go all-in on it, but I'd have to bootstrap everything myself, probably take a significant pay cut initially, and face the very real possibility of failure.

Everyone had opinions. My dad said "take the big company job—it's safe!" My entrepreneurial friends said "you're crazy to pass up this opportunity!" My wife, Amy, was supportive but stressed: "We have a mortgage, David. Can we afford the uncertainty?" Even my therapist pointed out that my personality tends toward anxiety, which might not jive with entrepreneurship.

I was paralyzed. Part of me desperately wanted the security of a big salary and good benefits. The other part kept thinking about all the ✅ successful startup founders I'd read about. I needed some kind of decision maker system to cut through the noise and help me make a choice based on what I actually valued, not what everyone else thought I should value.

🔧 The Fork in the Road: Three Very Different Futures

That's when I discovered WADM (Weighted Average Decision Matrix) from a startup podcast. I know it sounds corporate, but I needed to stop making gut decisions about a six-figure gamble and actually think through what mattered most to my life.

Instead of just two choices (job vs. startup), I realized I actually had three real options to consider:

My Three Potential Paths:

1. Take the Senior Manager Role - Join the unicorn startup, build my resume, and gain leadership experience

2. Join a Smaller Startup - Accept a role at a mid-stage company with less prestige but more equity upside

3. Go All-In on My SaaS - Quit everything and focus 100% on building my own company

📊 My Decision Factors & Priorities

The WADM 🔧 process forced me to get specific about what I actually wanted from the next 3-5 years of my career. Not what society said I should want, but what would actually make me happy and ✅ successful:

Financial Security & Growth Potential (35%): Let's be real—money matters. I needed to feel confident about paying our bills and eventually buying a house.

🎯 Personal Fulfillment & Passion (25%): I couldn't spend 50+ hours a week on something that didn't excite me or align with my values.

📈 Learning & Skill Development (20%): I wanted to grow, not plateau. Which option would make me a better engineer and leader?

⚖️ Lifestyle & Work-Life Balance (15%): I was already working 60-hour weeks. I wanted something sustainable.

🚀 Long-term Career Flexibility (5%): Which path gave me the most options down the road?

📊 The WADM Career Decision Matrix

Once I had my priorities figured out, it was time to 📊 score each option honestly. This was the moment of truth:

FactorWeight(%)Senior Manager RoleSmall StartupFull-Time SaaS
Financial Security & Growth35976
Personal Fulfillment & Passion25679
Learning & Skill Development208910
Lifestyle & Work-Life Balance15765
Long-term Career Flexibility5887
Total1007.707.307.45

Click to import this decision case into the editable WADM tool

🔧 The Surprising Truth About the Numbers

I'll be honest—these ✅ results surprised the hell out of me! As someone who'd been leaning toward the senior manager role for months, I was shocked to see it only won by a narrow margin: Senior Manager Role at 7.35, Small Startup at 7.25, and Full-Time SaaS at 7.15.

Here's what the numbers revealed:

The Senior Manager Role (7.35) won on financial security (9/10)—the salary was amazing, the benefits were comprehensive, and the company's stability was reassuring. But it 📊 scored lower on passion (6/10). Don't get me wrong, the work would have been interesting, but I knew I'd always wonder "what if?" The Small Startup (7.25) was surprisingly close behind. Higher learning potential (9/10) because I'd wear mul📌 tiple hats and see the whole business. But moderate financial security (7/10) because startups are risky. Full-Time SaaS (7.15) 📊 scored highest on passion (9/10)—this was MY thing, not someone else's company. But the financial risk (6/10) and lifestyle concerns (5/10) about working 80-hour weeks worried me.

📌 The Plot Twist: Second Guessing the Math

Seeing the ✅ results, I almost panicked. I'd spent months fantasizing about the senior manager role, but the WADM showed it wasn't dramatically better than the other options. The "winning" 📊 score of 7.35 felt... underwhelming? Shouldn't the right choice feel more certain?

That's when my wife Amy made a brilliant observation: "David, you're looking at these 📊 scores like they're a ✅ final exam. But what they're really showing is that you have THREE good options. Maybe the question isn't 'which is perfect' but 'which is good enough AND feels right for us right now?'"

✅ Our Decision: The Third Option (Sort Of)

Here's what we decided: I'm taking the Senior Manager Role, but with a twist.

Why? Because while the WADM showed all three paths were viable, the senior role gave us the financial security we needed to make smarter decisions about my SaaS. I'm planning to keep working on my company part-time for the first year, see if I can grow it to $20K MRR, and then reevaluate.

If my SaaS hits that milestone? I'll have a choice: go full-time with more capital cushion, or sell the business and focus on my corporate career. If it doesn't grow? I'll have valuable leadership experience at a ✅ successful company and no regrets about taking a calculated risk.

🔧 The Real Learning: 📊 Data Informs, You Decide

This decision making framework taught me something crucial: the goal isn't to find the "perfect" choice—it's to find a choice you can commit to fully and live with confidently.

Looking at the numbers, I realized the senior manager role wasn't just about money (though that mattered). It was about giving myself options and building the skills that would make me a better entrepreneur if that's the path I eventually choose. The WADM helped me see that being strategic sometimes means playing the long game, not taking the flashiest shot.

If you're facing a major career decision, don't just follow your passion or chase the highest salary. Get specific about what you actually need from the next phase of your life, weight those priorities honestly, and let the 📊 data guide you toward a choice you can feel confident about.

The "safe" choice isn't always the wrong choice—especially when it's part of a larger strategy.

P.S. - Six months later, my SaaS is at $15K MRR, I'm thriving at my new role, and I've never felt more confident about my career direction. Sometimes the second-best choice is exactly what you need.