Midnight Stroll

"What do you think I should do?" Jesse asked as we ducked under a tree.

"Do you want me to gently stroke your ego, or do you want me to tell you what I really think?"

"They're mutually exclusive?" he cringed.

"Oh, I can artfully merge them together."

"Go on, then. Give it to me straight."

"Okay," I sighed. We stopped on the path and he looked at me. "I think you've been working on this business part-time for too long. I think you've been talking about moving to France and growing this business, but you're just working and working and working on the side, safe enough with your paycheck from your full-time job that you could go on like that forever. And someone is going to beat you to the punch. They are. You'll have fun on the business and learn a lot, but I don't think it will be what you want it to be."

"Okay..." he said. "So, what should I do?"

"Whatever you want to do. Look, I'll be your mirror and tell you when your actions aren't lining up with what you say you want. But I'm not going to tell you what to do.

You just need to decide. Quit your job and really go for this business, or don't. If you quit your job, you're taking a risk, so of course there's a chance you'll fail. But there is also a chance you'll achieve everything you ever dreamed of. And wouldn't marching towards either one of those outcomes be an incredible adventure, in and of itself? If you fail, at least you will have failed while going after what you want.

But if you don't quit your job, you'll be nice and comfortable and secure, but you're almost certainly going to fail. It's at that point where you just need to commit to it or accept that it's a fun side-project that might bring in a little money on the side but isn't going to get you to France or doing all those big things you dreamed of. Your life is not going to drastically change unless you do.

And hey — that's perfectly fine, if that's what you want and what will make you happy. It's just that I know you, and I know that's not what you want, or what will make you happy. And I want to see you happy.

So that's what I think. I think you need to decide who you are in relationship to this situation. Just decide. Be like Alexander The Great — 'Nothing is worse than indecision. Be wrong. But be wrong, decisively.' Or as I like to say — 'Make a decision, then make it the right decision.'

And believe me — I know how hard that is. I've procrastinated on decisions like this a lot, so it's not like I'm any better at this than you. But if you don't make a decision, I just see us having the same discussion in a year and you'll always be waiting, waiting, waiting for the time to be right. What if the time is right now? What if you just go for it and back yourself? Jump off the cliff and assemble your wings on the way down. You are so smart and capable, and there are so many things I admire about you. You have everything you need to make this happen. I know you can do it."

Jesse looked into my eyes. "I love you. You know that, right?"

"You've mentioned it a few times," I giggled.

"I just don't know if I'm ready to quit my full-time job."

"Then ask your boss if you can drop to part-time, and phase into it. You're the glue in that place. Trust me. They won't want to lose you."

"He's so old-school, though. He won't allow it."

"Then be prepared to quit," I said. "He can have you part-time or not at all. I think you're way more valuable than you're giving yourself credit for. And you're very good at going after what you want, so this is just your ego throwing a tantrum, giving you a temporary crisis of confidence.

Besides, in the worst case scenario, you've got savings. You'll be fine. As my mom always says, 'if you don't ask, you don't get.' So just ask, and be prepared to walk if you don't get what you want."

"But-"

I leaned in closer and kissed him. "Come on, Jesse," I whispered. "Save yourself from the oblivion of non-realization."