Are You Ready to Chase Your Entrepreneurial Dream? 5 Questions to Help You Decide

As a techie in your 30s, you may feel you’re past the age for your entrepreneurial adventure. Perhaps sometimes you debate if  you should give it a shot after all – for if not now, then when? But are you ready to give up the stability offered by your high-paying tech job? How do you know if the time is right? 

Here are 5 questions which will help you answer if you are truly ready to be an entrepreneur?

1. Every Thanksgiving, ask yourself:  “Am I excited about next year?”

Leaving a fat, stable paycheck to jump into the unpredictable, unknown world of entrepreneurship is hard! So, when do you know it’s time? Make it a rule to ask yourself every thanksgiving – in my current role, am I truly looking forward to next year? Am I excited?

If your answer is anything other than “Hell, yeah”. You need to move. You are ready for a change. And its probably time you seriously consider your entrepreneurial dream. Follow Jeff Bezos’s famous regret-minimization-framework which begs the simple question – In X years, will I regret not doing it?

As Bezos himself puts it: “I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed, I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried.”

2. Do you have financial and emotional support?

We often think that if we get married, we may not be able to accomplish our entrepreneurial dream. The truth is the opposite. A partner can be the biggest support you can have in the lonely journey of an entrepreneur. Not to mention how much of a financial support they can be during the tough times.

Your closest friends are not to be underestimated either. When nothing goes your way, all you want is a shoulder to lean on and someone to motivate you. Make sure you have your social-support system. Network with other entrepreneurs. Only they truly understand what you are going through.

3. Are you ready to put your money at stake and maybe lose it all?

Scroll through LinkedIn and you will constantly read about startups getting funded with millions of dollars. You start to believe that all you need is an idea and you will raise money. But, speak to any entrepreneur who has raised money and they will tell you about the time and money they poured into the business to get traction before they got any attention from investors. So, are you ready to put your hard-earned money at stake and in the worst case, lose it all? 

4. Are you ready to get your hands dirty?

As an entrepreneur, you will be a one-person-army. And for a long time! As a tech entrepreneur, you may very well be an engineer one day and a salesperson making cold calls the next. If you are a food entrepreneur, then you are the cook, the manager, the server, and the dishwasher. Whatever your venture is, you need to get your hands dirty. You own your business and you may need to do it all. You may eventually find help and build a team but when push comes to shove, you don’t say – that’s not my job. Do you envision yourself doing it all?

5. Do you have an exit plan?

On your entrepreneurial journey, you could lose sight and forget to evaluate when it’s time to cut your losses. Remember, a startup is both highly rewarding and risky. Have an exit plan before you jump in and each thanksgiving, re-evaluate if its time to change direction or call it quits.

There is absolutely no shame in changing direction or quitting if the data suggests so. Remember how Netflix used to be a DVD Rental service before they pioneered to online streaming? Sprig, a meal-kit business, called it quits after 5  years of business. Their business model wasn’t sustainable.

Moral of the story – listen to your data and be ready to make major changes if need be.

Did you answer yes to all five? Congratulations, you are now all set to jump onto the entrepreneurial boat. Meet you at sea! It’s going to be a one, fun, bumpy exciting ride.