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Not very long ago, I was making a healthy salary in technology. I worked at huge success companies: one is now a billion-dollar unicorn, and another is on course to becoming one. For a period, I managed my day job and my dream. But there came a clear point when I knew I couldn’t do the both. It took a culmination of events, failures, and changes to go from comfortable money to pouring everything I had and had saved on my dream. Today, at the helm of a fast-growing company of almost 50 people, it’s a daily circus of risks. But I wouldn’t have it any other way.
Are you, like I once did, living 2 worlds? How do you know and when do you know? Perhaps answering these questions may help. Remember there is no right answer here. The only right answer is the honest one, and you only need to answer to yourself.
A. Yes, and Yes
B. Yes, No
C. No, No
Nothing influences your decision to quit your day job more than having other lives dependent on you. As a parent, it is your decision to raise your children on simple minimums or more extravagant love. Whatever that monthly amount, if you are at answer (B) you may be making a rash decision quitting the day job.
A. Go back to a day job,
B. If after everything my venture fails, I’ll start another business
Entrepreneurship is a way of thinking and a permanent lifestyle choice. There is no fairy godmother to wave dreams come true overnight. It’s perseverance in the face of endless heartbreak before any real success happens. If the day job is a backup to rush back to after 12 months, then it’s perhaps not a good idea to leave it at all in the first place
A. Nope. Even making CEO at my corporate job would not excite me
B. I love it, promotions and pay hikes validate my hard work. I want to make VP/CXO of this company some day
If you said (A), I felt like you do. I knew it was time to leave my day job because when I imagined all the promotions to the top, the vision of success did not animate me. At the same time, I know hyper-sharp, wonderful people that make promotions every year and love the climb. What floats your boat?
A. Married by 29, kids by 34, VP by 35, $$M saved by 40. I get a rush knowing I am doing better than my circle of friends
B. What matters is having total control of the steering wheel. I thrive on change and edit the plan as I go
Early stage companies manage daily turmoil. You need to acknowledge a life where daily change is the norm, not the exception. Is (B) you?
A. What else will I take a chance on if not myself?
This stressful situation shall pass. I tackle what comes my way and I always come out stronger.
B. Going to plan makes me feel in control. By being intelligent and proactive, I eliminate risk and stress
I don’t think I understood what ultra-high, palpitation inducing stress was until I started running a company. Answering (A) theoretically only part prepares you for facing the stress. But over time, you learn to control the risks, and feel in control no matter the upheavals.
A. Yes, and it sucked. But I wouldn’t be who I am or where I am if not for learning from those failures
B. Not that I can think of. Failure scares me, I wonder how I would fare with failure.
Entrepreneurship is lonely, it is heat break, heart burn, self-doubt, many ultra-crappy days. But if you have failed BIG before (not a failed test or a drunken Instagram picture), it prepares you for this step. If you’ve lost all your money on your last venture, been fired, divorced – you are a survivor. You know how to fail and get back up on your feet. You know that the key is to take baby steps. One day, one small challenge at a time.
A. It is important I prove myself to others.
B. I only compare myself to me. I am first accountable to myself.
If you answered (B), you know to block out others’ voices. People may be well intentioned but their expectations and ideas can drive you nuts. Answering to others, comparing to others’ lives or progress is a death knell for an entrepreneur’s idea
A. Money drives me but does not define me. The idea of losing my money does not impact my self-worth.
B. I cannot put everything I’ve worked hard for at risk. Losing my hard-earned money would devastate me.
Ironically the willingness to put all at risk allows you to mentally invest in building a higher-value future. If you’re at (A), you’re able to look at NOT what you may be losing but how much more you can build when you invest in yourself
A. Making my own destiny and risking all if needed to make my dreams come true. Enjoying every moment of the ride following my purpose.
B. Following a plan and structure. I am proud of my salary, and the career I have built. Enjoying every moment of the ride following my purpose.
You see both answers to question 9 lead to the same answer. Because there isn’t one right answer. The right answer for you is the one which leads you to your purpose.
I didn’t go through a list like this to decide if it was time to quit my job. If I’d tried this list, I may not have known where I lay on some of the questions. To others, my answers may have led me to believe I wasn’t ready for the jump. In just the few years I’ve started my company, my thinking has evolved drastically. And yours will too. Who you are when you take the plunge is NOT WHO YOU WILL BE a year or 2 after you take the plunge. You take the risk because you know you will deal with whatever comes your way as it comes. And sometimes that conviction is all you need to make the decision.
The media and press glamourize the entrepreneur, the risk-taking adventurer. It’s a bunch of hackneyed, suffocating hype. True glamour and honor comes from knowing who you are, knowing what drives you and makes you happy. It takes courage to take the plunge into entrepreneurship. And it takes equal courage and honesty and spine to announce to yourself, and your world that being an entrepreneur isn’t really you.
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