Experienced entrepreneurs (who have “been there, done that”) often ask the question, “So, what keeps you up at night?”

Short answer: My kids. And more specifically, my younger son, Quinn Alexander Yoskovitz, who recently turned 1 year old. He’s been a bit under the weather, teething like a werewolf and grumpy like a seriously-constipated old man (and if you’ve ever met one of those, you know what I’m talking about!) This all translates into a complete lack of sleep. For the past year I’ve lived on about 4-5 hours of sleep per night. Some nights are better. Some are worse. A couple nights ago I got a grand total of 2 hours of sleep! The night ended (and the day started) with me driving Quinn around the city so he’d sleep in the car. A large coffee, bagel, triple shot cappuccino and chocolate biscotti later, I dragged my ass home, exhausted (having driven around for 1.5 hours), with a vicious stomach ache. That was some day!

On a positive note, look how freaking cute he is…

(That’s Quinn’s older brother Sam in the right picture.) But enough about those darn kids…what else keeps me awake at night?

Well, there’s this little thing called Standout Jobs that keeps me fairly occupied during the day. And running a startup will keep the most easygoing of us awake at night.

All of that combined helps explain why I haven’t posted here as much as I’d like. But this isn’t about making excuses, I really do what to get some things off my chest (and hopefully these thoughts prove useful too!) So here are a few other things that keep me awake at night…

4 More Things That Keep Me Awake at Night

1. The Difference Between Quick and Rash Decisions. CEOs and startup founders are forced to make a lot of decisions. It comes with the territory. And if you’re not a veteran entrepreneur you won’t have a lot of past experience to rely on. And you have to make the decisions quickly. Like … right now. Hurry up. Come on! Slow startups fail. You know it, and it means you have to make a ton of critical decisions constantly & very quickly. But are you making rash decisions? Quick and rash go hand-in-hand, but you don’t want to make rash decisions, because they’ll usually be the wrong ones. I don’t have a solid answer at the moment, and I think this is a subject I could explore in a lot more detail later on.
2. Hiring Great People. If you’re not worried about hiring great people and making the right personnel decisions you’re doing something wrong. Seriously. And for a startup like Standout Jobs which is right at the threshold of evolving from a technology company to a sales/marketing company those hiring decisions become even harder. We know how to hire great technical talent…but hiring outside our comfort zone is another story.
3. Puzzles. I think of startups like puzzles – at least the kind that have multiple ways of reaching the same conclusion. There’s no one absolute answer to a successful startup, but there are still a million pieces that all have to fit together properly at some point. A lot of this comes down to managing the day-to-day operations effectively. That’s something I have a good handle on, but as you start to think about longer term strategic initiatives, future product development, sales strategies, etc. … the puzzle keeps my head buzzing.
4. My Health. Startup founders can’t balance everything all the time. It’s impossible. Something has to give. It’s not that you can’t achieve some amount of balance (and truth be told, you have to keep laughing about things otherwise you’re doomed!) but from time to time things will suffer. In my case that’s my eating habits. You’re in a rush, you eat crap. You’re tired, you eat more crap. Ugh. Ugh. Ugh.

So why do it?

The answer is simple: This is what I love to do. It’s what I was meant to do. No one said it’d be easy, but you don’t ask a professional hockey player why he suffers through all the aches, pains, injuries, ups and downs, etc. to play hockey at the highest level, right? They’re trying to be the best. They’re trying to win. They’re trying to make tons of money. And they love what they do.

The same holds true for startup entrepreneurs. Why go through it all? You better damn well love it…

And on that note, what keeps you awake at night? Please share!