Should I Start a Side Business?
The dream of a successful side business is powerful—it offers the promise of creative freedom, extra income, and even a path away from your day job. But the reality is often a grind of late nights and slow progress. This guide will help you approach the decision with a clear head. We’ll use mental models to help you look past the hype and honestly assess if you have the time, the energy, and a truly viable idea to make it work.
Capture this play inside the Decision Log and make it your own.
Step 1: What is Your "Why"? (The Motivation Test)
First, let's be brutally honest about why you want to do this. People often start a side business for one of two reasons: as a "vehicle" or as a "passion." Neither is better than the other, but knowing your motivation is key.
Is this a vehicle to an end? (e.g., "I want to make an extra $1,000 a month to pay off debt," or "I want to quit my job in two years.") If so, you should be ruthlessly focused on the most efficient path to that goal, even if the work isn't your life's passion.
Is this a passion project? (e.g., "I just love designing furniture and want to share it with the world.") If so, you might be willing to work for years without a significant financial return because the work itself is the reward. Be honest with yourself. If you say it's a passion but you secretly need it to be a vehicle, you are setting yourself up for disappointment.
Step 2: The "Painkiller vs. Vitamin" Test
The best businesses solve a real, urgent problem for a specific group of people. They are painkillers, not vitamins. A vitamin is a "nice-to-have." People know they should use it, but they forget and don't really miss it. A painkiller solves an immediate, throbbing pain. People will actively seek out and pay for a solution.
What is the "pain" your idea solves? Is it a real, burning problem? And who has it? The more specific you can be, the better. "I help busy moms" is a weak starting point. "I create meal plans for busy moms of toddlers who have picky eaters" is a painkiller. Before you build anything, you must be able to clearly articulate the pain you are solving.
Step 3: The Validation Gauntlet - Get Signals Before You Build
The single biggest mistake new entrepreneurs make is building something for months in isolation, only to find out that no one wants it. You must validate your idea by getting real-world signals before you invest significant time or money. The goal is to get your first "proof of life" as quickly as possible.
The "Pay Me Now" Test: The only true validation is a stranger's credit card. Can you get someone to pre-order your product or pay for your service before it's even built? This is the strongest signal you can get. Ask for a small, symbolic amount. "It will be $50 when it's done, but you can pre-order it for $5." If you can't get anyone to do this, your idea may not be as strong as you think.
The "Landing Page" Test: Create a simple one-page website that describes your product or service. Drive a small amount of traffic to it (from your social network or a tiny ad budget). Is anyone interested enough to give you their email address for a waitlist? This is a weaker signal than payment, but still valuable.
The "Manual First" Principle: Before you build an automated course, a complex app, or a scalable service, can you deliver the promised value manually? If you want to build a course, can you first find 3 people to coach one-on-one? If you want to build a software tool, can you first perform the task for someone as a consultant? This forces you to learn exactly what your customers need.
Step 4: The Time and Energy Audit
A side business doesn't run on passion alone; it runs on hours. You need to do an honest audit of your time and energy. A side business requires a consistent commitment, even when you are tired and unmotivated.
Look at your weekly schedule. Where will you find 10-15 hours of focused work time, every single week, for at least the next year? Be specific. "I'll wake up an hour early on weekdays and work for 5 hours on Saturday morning." If you can't find this time, you are not ready to start. A side business is a marathon, not a sprint, and consistency is the only thing that creates momentum.
Step 5: The "Can I Afford to Lose?" Test
Every new business is a risk. You must be willing to lose every dollar you put into it. This is your Risk Capital. It is money that, if it vanished tomorrow, would not materially impact your life. You would be annoyed, but you could still pay your rent and buy groceries.
For most service or digital product businesses, you can start with very little risk capital (a few hundred dollars for a website and some software). For businesses that require inventory, the risk is higher. Know your number. If you can't afford to lose it, you can't afford to start.