Should I Leave My Job?

By Sean Platt

Frustrated writer

Today’s question is a big one, when is it safe to leave my job?

(If you prefer audio, you can listen to this episode on the Smarter Artist Podcast)

That is a hard, hard question to answer and yet we get asked it all the time.

I only have my own experience to draw on here and this is absolutely not advice. But it is a question that is asked almost as much as any other, and I do think it’s worth a small episode.

But again, this is just my experience. I would actually say I did it way too fast. I jumped without looking. I lost my house.

I took on a lot of debt to make this happen, and even after I paid it off and was semi sort of back on top, I left a really high paying jog to risk it all again. It took a couple of years to make it happen even then.

Right now things are nice, I’m comfortable, I’m paying off the very last of my debt and things are going well. But it’s taken seven years to make that happen.

In that time I was very determined, I was willing to work 70 hours without vacations. I mean I worked at least 70 hours over seven days a week for seven years. I’ve taken very few days off.

That’s not easy. Not everyone can do that.

I had a fantastic support system. My children believe in me, they encourage me. My wife, Cindy, is my best friend and she’s an eternal cheer leader who has an unreasonable amount of faith in me and allows me to make mistakes and allows me to bury myself in my bedroom and just work, work, work. My office has been our bedroom for years. She’s a little tired of that, but she also is supportive of it.

If you don’t have a support system like that, it’s going to be very difficult to make this work and you might be better served doing it a little bit on your spare time.

We have one person in our mastermind who I think is just a genius. I love the way he’s put this out there where he has a job that he doesn’t love. He likes it and he’s good at it, and he’s well compensated for that job, but he also has a ten-year plan. He’s not in a rush to leave.

He spends a lot of his free time on writing, and I don’t think there’s a lot of [free time]. The guy has a full-time job and it’s a demanding career. He has a wife and a child, but he also has a plan. And he chips away at his dream constantly.

He is willing to spend money on education and things that teach him to be a better writer, and a smarter marketer. He’s constantly got a book going, or multiple books going actually.

I think that’s a smart way to do it. Certainly his way is smarter than mine. I’m just not that patient.

I’m patient in a global sense. I have really, really big goals, really big dreams, a lot of ambition. So, it’s easy to be patient because I know I’m chipping away at it.

But I can’t just sit and do nothing. I can’t sit at a 9-5 job. I’ve never had one. I’m a little unemployable in that way.

I think that even now I’m able to augment my success because I have two awesome partners. Without Dave and Johnny I’d still be struggling.

When to leave your job is totally a personal decision. But you should never ever do it before you’re ready. More importantly, you should never do it before your family is ready… Just know what you're in for and be ready to do the work, because being a creative entrepreneur is amazing.

So,Leaving your job is a personal decision. Just know what you're in for & be ready to do the work; being a creative entrepreneur is amazing! Click To Tweet

For me that was the dividing the line there.

Yes, it was really risky for me, for us, and it was really hard and even after all this time we still barely made it. Things are good now but we had to see the other side of that. But the bottom line is, I was ready and my family was ready. We were ready for those risks. We were ready for the hardships that were going to come with those risks, and we looked them in the eye when they got here.

If you can’t do that, that’s okay.

What we did, it’s arguably kind of foolish. It worked out for us, but it could easily not have worked out for us. So, just know what you’re getting into when you do it.

I will say that the rewards on the other side are amazing, and if I did it, so can you.

couple innocently embraced in a lovely green fieldJust know what you’re in for and be ready to do the hard work, because being a creative entrepreneur is an amazing thing.

You get to make the rules, you get to make the business. You get to do fun things and work with awesome people.

But it is relentless and you and you have to have the ass in seat time, and you have to have the support.

So, whatever you decide, best of luck. 

Sean Platt is the founder of Sterling & Stone and loves that he not only gets paid to make up stories and come up with crazy ideas, but that he gets to do so with his best friends. Together, they've also co-authored the bestselling non-fiction titles Write. Publish. Repeat., Fiction Unboxed, and Iterate & Optimize to help Smarter Artists get smarter, faster.

Sean lives in Austin, Texas with his wife Cindy and their two children, Ethan and Haley.

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