When should I quit my day job to pursue my dream?

I tell budding entrepreneurs that in my opinion, the right time to leave is when your side venture produces as much income as your day job. In reality, it’s not that straight forward. It depends on what you’re trying to build and the capital (human and financial) you have behind it.

That being said, it would be wise for you to build up and set aside 6-months cash as a personal emergency fund. Let me say that again, as a PERSONAL emergency fund — not for business. In today’s world, you (and more importantly, your family) should have a lifeline as you scale that mountain.

Believe me, I know all the stories of entrepreneurs who risked everything and when they were down to their last dollar they were somehow able to save the day. In fact, two of my five tech startups were like that. Still, what percent are able to pull a rabbit out of the hat? The odds are only a fraction of any wager you could possibly make in Las Vegas. You might as well lay everything down on the pass line in craps and go for that 7 using dice loaded against it. Is it possible? YES! Should you count on it? NO!

I can just see it now, “In just 4 hours at night I make half of what I do at my day job… I think it’s time to quit.” Who wouldn’t want to leave their “job” to pursue their “dream?” Let’s see… job vs dream? Hmmmm. Unfortunately, it’s a fallacy to assume that more time will produce more revenue. What if you dedicate 12 hours a day and make the same amount because the market isn’t quite ready or what you think it is? Timing is huge and if you’re not careful it will be a sobering lesson.

I’m not here to throw water on your entrepreneurial fire. Go ahead and lead with your heart but keep your head involved. My Dad once told me of a miner who sunk a test shaft in search of precious metals. As he went along, he took samples. When he got the results back, he found that there was a high concentration of gold. So, he went all in but the thing went bust. Why? Because he only took a sample when he saw color in the soil!

Would my younger self have waited for the “right” time?… I would hope so but perhaps not. I’m sorry to say but many entrepreneurs are not only fearless but also shortsighted. Still, you don’t have to rely on “dumb luck.” Make it happen but be smart along the way.

If you want to win the day, one of the most important things you can do is learn to problem solve. Don’t be discouraged by obstacles. See them for what they are… opportunities to learn. Take the time to think your way through and then take a step. Continue doing so until you navigate your way around (or over or under) whatever it is. Eventually, you’ll realize that obstacles are your ally — a barrier for you is a barrier for others. Without barriers, others can easily follow your example and potentially win the day.

Today’s takeaways:

  1. Get a mentor (or two) or do what I did and take smart, been-there, done-that people to lunch on a regular basis. Who doesn’t want a free lunch? Use each lunch to explore the most important thing you’re working on. Tell the person everything you know about that one thing and then LISTEN to what they have to say. Remember, you’re there to get counsel, not sell!
  2. There is always a way. Once, I really wanted to talk with this guy but he was too busy (scheduled several weeks out). All he had open was a single lunch appointment but he lived in another state. So, I set up the lunch, contacted his admin, found out what restaurant he liked, called that restaurant and had them deliver his favorite dish. Then, we chatted over Skype while eating. He was so impressed that he made a few phone calls on my behalf and the door that I was having difficulty opening was all-of-a-sudden open. Imagine that (and all for the cost of a $35 lunch, including gratuity)!

As a side note, entrepreneurship is like women and child bearing… “the excitement of first learning you’re pregnant, the challenges and complications that follow, finally, the birth of a beautiful baby.” For serial entrepreneurs, I would add “time passes, memory fades, and you want to do it again. It’s not long, however, before you may say, ‘what was I thinking?’ 🙂”

Movie Quote: “Somewhere along the line we stopped believing we could do anything. And if we don’t have our dreams, we have nothing.” — The Astronaut Farmer (2006)

When should I quit my day job to pursue my dream? was originally published in The Mission on Medium, where people are continuing the conversation by highlighting and responding to this story.

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Author: Robert Bishop

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