The dream of entrepreneurship exists in the minds of the ambitious, the ones who believe they can reach for the stars.
And in their minds, they can see it.
They know what they want to build — and if they don’t know what to build, they know they just want to build something!
But before you go leaping for the stars, I encourage you to ask yourself these 20 questions.
Otherwise your leap of faith will turn into you leaping and falling on your face.
1. Do you know what it is you want to build?
I would argue that the number one mistake most entrepreneurs make is they raise money (or take the leap with their own money) before they even know what it is they really want to build.
Why would you ever do that? A decision like this turns your runway into a creative exercise instead of time to execute.
2. Do you have a reliable income stream?
If you are a first-time entrepreneur, and you want to take the leap out of your 9–5 to invest all your time into your endeavor, do you have a way to keep the lights on?
Do you have projects lined up?
How are you going to make this a long-term play instead of a short-term decision.
3. Do you have a strong network?
When you take the leap, do you have a group of people you can turn to for advice?
For potential client referrals?
This is crucial.
4. Have you tested your work ethic yet?
Big mistake aspiring entrepreneurs make is they put themselves in situations of freedom without ever testing their own ability to make good use of that freedom in the first place.
Test your work ethic before you go and take the leap.
5. How much runway do you actually have?
How much money do you have saved up?
How much funding do you have? What is your overhead?
If everything goes wrong, literally everything, how long do you have before you’re eating ramen for breakfast, lunch, and dinner?
6. Do you have revenue lined up before you leap?
In addition to having runway, do you have projects lined up so that you have enough work to keep yourself busy for a few months?
7. What is your long-term play?
You don’t have to have a perfect answer here, but what’s the big vision?
And how are you going to pay your bills immediately while still working toward the end goal?
8. Can you handle being the marketer of your business, the one executing the work, and the one handling the accounting?
If you’ve never done all three of these things, even with tiny projects on your own, get yourself some practice first.
9. Do you have mentors you can call for help along the way?
Having 1 or 2 mentors in your corner as you take the leap is essential.
You aren’t going to know how to do everything. You’re going to need to ask for some help.
10. What’s your anticipated daily schedule going to be?
Once all 24 hours per day are yours, how are you going to spend them?
Sitting alone in your apartment is a risky strategy — you’ll lose your mind at some point.
11. Who can you collaborate with to move toward your goal faster?
Of the projects you want to pursue, who can you bounce ideas off, or trade services with, or co-create with to get things done, faster, for the both of you?
12. What’s your marketing strategy going to be?
Now that you’re responsible for getting your own clients, or selling your own products/services, how are you going to do that?
How do you plan on putting food on the table?
And do you have any sort of momentum in that direction yet? (If not, start now.)
13. Do you have proof of concept?
Even if your plan is to freelance, do you have proof that people want to work with you? (And that proof has to be people actually, you know, working with you.)
14. How are you going to measure your success?
If you’re a startup, how are you going to prove to your investors that their money is being invested well? If you are a freelancer, how do you judge success your first year? If you are selling products, what margin are you aiming for? Measure, measure, measure.
15. How bad do you want it?
Entrepreneur life isn’t easy.
It’s going to ask a lot of you. So you need to know, long before you actually take the leap, how bad you want it. Are you ready for that path? Are you willing to sleep on couches? To travel? To do whatever it takes to bring your dream to life?
16. How far are you willing to go to succeed?
Building on the previous point here, where is your “no” line?
Would you move across the country? Would you invest everything you had in yourself?
How far are you really willing to bring this dream of yours to life?
17. Who are you reading and studying?
It’s a mistake to go off on your own and think you have everything figured out.
That’s literally the worst thing you could do. Keep your mind open. Keep studying. Keep learning.
18. How can you stay lean?
Staying lean does not just mean “saving money.”
If you are too much in penny-pinching mode, you’ll miss opportunities to grow and expand. But if you are in spending mode, you’ll blow through your runway. Focus instead on staying lean. Keep yourself nimble. Don’t take on overhead.
Use your income to move fast and pivot when necessary.
19. How are you going to prioritize your daily To Do lists?
As soon as your schedule becomes yours, you are in charge of prioritizing what’s on your plate.
How are you going to do this? What are your immediate goals and what are the things you can postpone to a later date?
20. What happens if you fail?
And of course, what happens if it all crashes and burns?
Are you ok with picking yourself back up again? If this project doesn’t turn out the way you thought it would, are you ok with that? Are you in this for the lessons you can learn?
What is your intention for doing your own thing?
Before you go taking the leap, be sure to ask yourself these questions.
They can be valuable indicators as to whether you are ready or not.