5 Things That Keep Me Awake At Night

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5 Things That Keep Me Awake At Night

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…

Quinn Alexnader Yoskovitz Quinn and Sam

(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

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.
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.
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.
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!

If you enjoyed this post, please share it!

June 1, 2008 Posted in Humor, Startups by Ben Yoskovitz

http://loanofficersurvivaltraining.com Genuine Chris Johnson

The path.

I am on the path that I want to be on right now, and I want to stay on the path, but despite the fact that there are people like you, Fields, etc,

…there are always people that are telling you the path is elsewhere. And the amount of faith that you have to have is insane to make it in this business.

Am I nuts?
http://loanofficersurvivaltraining.com Genuine Chris Johnson

The path.

I am on the path that I want to be on right now, and I want to stay on the path, but despite the fact that there are people like you, Fields, etc,

…there are always people that are telling you the path is elsewhere. And the amount of faith that you have to have is insane to make it in this business.

Am I nuts?
http://www.sddreamweavers.com Aaron Wood

The thing that keeps me up at night? Have I done everything possible to make my customers successful? I usually have done everything possible but I always do this to keep myself on my toes.
http://www.sddreamweavers.com Aaron Wood

The thing that keeps me up at night? Have I done everything possible to make my customers successful? I usually have done everything possible but I always do this to keep myself on my toes.
http://ozlady.com Stephanie

Stuff I haven’t done – being a startup entrepreneur invariably means that a lot of things rely on me to get them done. I am gaining reliable staff slowly (refer your point 2), but there is the trust issue (another thing that keeps me awake).

I’ve already had ideas stolen and staff (now ex-staff) try and set up their own businesses.

Some days you wonder if it’s worth it.
http://ozlady.com Stephanie

Stuff I haven’t done – being a startup entrepreneur invariably means that a lot of things rely on me to get them done. I am gaining reliable staff slowly (refer your point 2), but there is the trust issue (another thing that keeps me awake).

I’ve already had ideas stolen and staff (now ex-staff) try and set up their own businesses.

Some days you wonder if it’s worth it.
http://mckinseytomainst.blogspot.com Vijay Goel, M.D.

Biggest thing for me is: Do I and each of my team members know what the 2 most important things each of us have to get done are in the short/medium/longer medium terms?

There are so many choices and so many ways to waste time– but letting the unimportant ones fall and getting the important steps for development/growth done– this is what will make or kill my business’s ability to storm the beaches of Normandy on our launch date.

I find it somewhat ironic that my health as well has been on the backburner– and my company’s mission is to help consumers engage in their health choices…
http://mckinseytomainst.blogspot.com Vijay Goel, M.D.

Biggest thing for me is: Do I and each of my team members know what the 2 most important things each of us have to get done are in the short/medium/longer medium terms?

There are so many choices and so many ways to waste time– but letting the unimportant ones fall and getting the important steps for development/growth done– this is what will make or kill my business’s ability to storm the beaches of Normandy on our launch date.

I find it somewhat ironic that my health as well has been on the backburner– and my company’s mission is to help consumers engage in their health choices…
http://www.pacebutler.com/blog/ Recycling Mike

What keeps me awake at night? It’s the feeling that I haven’t done enough during the day. I know it’s unhealthy, and one could only do so much. Even when I’m already half-asleep, the feeling just comes, bam! and I’m fully awake looking at the sharp details of the things I failed to do during the day. I only get poised to go back to sleep once I’ve mapped out the steps I need to do in the morning.
http://www.pacebutler.com/blog/ Recycling Mike

What keeps me awake at night? It’s the feeling that I haven’t done enough during the day. I know it’s unhealthy, and one could only do so much. Even when I’m already half-asleep, the feeling just comes, bam! and I’m fully awake looking at the sharp details of the things I failed to do during the day. I only get poised to go back to sleep once I’ve mapped out the steps I need to do in the morning.
http://en.JiansNet.com Jian Chen

How to get more users to use my question and answer system, this is the #1 thing that keeps me up all night. Also, how to compete with Google in terms of the next generation search engine? It must be a search engine utilizing the mass wisdom and more user friendly as well.

So, all puzzles me…No answer yet.
http://en.JiansNet.com Jian Chen

How to get more users to use my question and answer system, this is the #1 thing that keeps me up all night. Also, how to compete with Google in terms of the next generation search engine? It must be a search engine utilizing the mass wisdom and more user friendly as well.

So, all puzzles me…No answer yet.
http://www.rednod.com Alistair

I think my filters for Great Ideas have gone way up. If I’m not compelled to lose sleep over how awesome it is, then it’s not that interesting. So, ironically, I’m losing sleep over what’s cool enough to lose sleep over.

That said — I’m doing a lot of online stuff on various sites and at various events these days. Juggling all of that, and lacking any real feedback on how well it’s going (if you don’t count Google Analytics) is something to lose sleep over.

Oh, and there’s the disconnect between how great mornings feel (like newly bought school supplies) and how I didn’t get to all the things on my list come nighttime. But I think all entrepreneurs feel that one.
http://www.rednod.com Alistair

I think my filters for Great Ideas have gone way up. If I’m not compelled to lose sleep over how awesome it is, then it’s not that interesting. So, ironically, I’m losing sleep over what’s cool enough to lose sleep over.

That said — I’m doing a lot of online stuff on various sites and at various events these days. Juggling all of that, and lacking any real feedback on how well it’s going (if you don’t count Google Analytics) is something to lose sleep over.

Oh, and there’s the disconnect between how great mornings feel (like newly bought school supplies) and how I didn’t get to all the things on my list come nighttime. But I think all entrepreneurs feel that one.
http://www.contextcreative.com Andy Strote

Gosh, so young and so earnest. Here are some suggestions for what should keep you up at night:

1. Did I drink enough beer today?
2. That steak I had for lunch – should it have been bigger?
3. Is it worth planning now for a middle age crisis? If so, which red convertible should I buy? And what multiple of my salary should it cost?
4. What etiquette is involved in going into a hard core bike shop and ordering a custom Harley?
5. Eliot Spitzer and me – contrast and compare.

Other than that, go for a good run before bed and get some sleep.
http://www.contextcreative.com Andy Strote

Gosh, so young and so earnest. Here are some suggestions for what should keep you up at night:

1. Did I drink enough beer today?
2. That steak I had for lunch – should it have been bigger?
3. Is it worth planning now for a middle age crisis? If so, which red convertible should I buy? And what multiple of my salary should it cost?
4. What etiquette is involved in going into a hard core bike shop and ordering a custom Harley?
5. Eliot Spitzer and me – contrast and compare.

Other than that, go for a good run before bed and get some sleep.
http://www.twitter.com/scottbradleyoc Scott Bradley

What keeps me up at night?

-Exciting ideas that I continue to work on
-The exciting times of new challenges that I am facing
-Thinking about different ways to solve problems that I have
-Sometimes…thinking about someone I am falling for
-The thoughts about how fruitful my future will be
http://www.NetworkingEffectively.com Scott Bradley

What keeps me up at night?

-Exciting ideas that I continue to work on
-The exciting times of new challenges that I am facing
-Thinking about different ways to solve problems that I have
-Sometimes…thinking about someone I am falling for
-The thoughts about how fruitful my future will be
http://www.insidesales.com/lead_response_management.php Troy Bingham – Lead Response M

Ha Ha! I feel your pain! I have a new born and no sleep as well. This is a good article but you left off gas prices. Other than that, you are right on.

lrmguru.blogspot.com
http://www.insidesales.com/lead_response_management.php Troy Bingham – Lead Response Management

Ha Ha! I feel your pain! I have a new born and no sleep as well. This is a good article but you left off gas prices. Other than that, you are right on.

lrmguru.blogspot.com
http://www.wrapmailblog.com Bill

1.Fear of writer’s block
2.Planning the next days To Do List
3.Wishing I had got everything done that was on today’s To Do List.
http://www.wrapmailblog.com Bill

1.Fear of writer’s block
2.Planning the next days To Do List
3.Wishing I had got everything done that was on today’s To Do List.
http://www.obsidianlaunch.com/blog Mike Michalowicz

1. My wife, when she rolls over in bed and kicks me. She’s a very active sleeper!
http://www.obsidianlaunch.com/blog Mike Michalowicz

1. My wife, when she rolls over in bed and kicks me. She’s a very active sleeper!
http://www.realestatevirtualassistant.net Ruth Ann Macklin

You won’t getting anymore sleep when your son is a teenager! You’ll be driving around town looking for his car when he is out past curfew.
http://www.realestatevirtualassistant.net Ruth Ann Macklin

You won’t getting anymore sleep when your son is a teenager! You’ll be driving around town looking for his car when he is out past curfew.
http://blogyourthoughts.com Daniel

Thinking of ideas of how to make more money, lol.
http://blogyourthoughts.com Daniel

Thinking of ideas of how to make more money, lol.
http://www.mclellancreative.com John Gillett

My kids kept me up as babies, toddlers…and now as teens. Now that they’re almost out of the proverbial nest I worry about the diintegration of freedom, jobs and integrity in America.
http://www.mclellancreative.com John Gillett

My kids kept me up as babies, toddlers…and now as teens. Now that they’re almost out of the proverbial nest I worry about the diintegration of freedom, jobs and integrity in America.
http://www.peerdreams.com Lacey

I usually sleep pretty well at night — I love my sleep! — but I find the times that I’m kept awake is when I feel like I’m on the edge of something new. And with a startup, that can happen fairly often. Sometimes the thought of, “What might tomorrow bring?” is exciting / nerve-wracking enough to keep me up for hours. Great post.
http://www.peerdreams.com Lacey

I usually sleep pretty well at night — I love my sleep! — but I find the times that I’m kept awake is when I feel like I’m on the edge of something new. And with a startup, that can happen fairly often. Sometimes the thought of, “What might tomorrow bring?” is exciting / nerve-wracking enough to keep me up for hours. Great post.
http://vbextra.com RainMan

Thinking of ideas of how to make more money, that’s good one Daniel i agree with you
http://vbextra.com RainMan

Thinking of ideas of how to make more money, that’s good one Daniel i agree with you
http://poker-spiele.blogage.de/ Ernesto

When I have done everything possible but I always do this to keep myself on my toes.
http://poker-spiele.blogage.de/ Ernesto

When I have done everything possible but I always do this to keep myself on my toes.
http://www.bussinesscards.org Stuart

I think health is the most important one to be honest. Too many Entrepreneurs concentrate too much on making money and stressing about work that they run themselves into the ground and cannot enjoy the benefit of their work.
http://www.bussinesscards.org Stuart

I think health is the most important one to be honest. Too many Entrepreneurs concentrate too much on making money and stressing about work that they run themselves into the ground and cannot enjoy the benefit of their work.
http://themoneyfx.com Julius

What keeps me up at night? blogwalking all night long…It keeps me up at night..:)
http://themoneyfx.com Julius

What keeps me up at night? blogwalking all night long…It keeps me up at night..:)
http://www.sportscentralcreations.com Cheryl P

Kids are still #1 for me….and my kids are grown. It seems that it doesn’t matter how old they get, their problems still cause you worries.

The 2nd for me is always business…and marketing is the #1 question. What should I do today, did the things did yesterday get results, etc.
http://www.sportscentralcreations.com Cheryl P

Kids are still #1 for me….and my kids are grown. It seems that it doesn’t matter how old they get, their problems still cause you worries.

The 2nd for me is always business…and marketing is the #1 question. What should I do today, did the things did yesterday get results, etc.
http://www.TheEnhanceLife.com/ Shamelle

Oh, your kids are adorable

For me, what mostly keeps me up at night are decisions! Big ones….

Also, sometimes, if I watch a movie, TV Series or read book half way and go to sleep, I’ll keep thinking about what might happen. That is of course if its really good!
http://www.TheEnhanceLife.com/ Shamelle

Oh, your kids are adorable

For me, what mostly keeps me up at night are decisions! Big ones….

Also, sometimes, if I watch a movie, TV Series or read book half way and go to sleep, I’ll keep thinking about what might happen. That is of course if its really good!
http://www.andrewflusche.com Andrew F

Those are some cute kids!

I feel your startup pains. I’m getting my solo law firm off the ground, so many similar things are keeping me awake at night as well.

But it’s loads of fun!!
http://www.andrewflusche.com Andrew F

Those are some cute kids!

I feel your startup pains. I’m getting my solo law firm off the ground, so many similar things are keeping me awake at night as well.

But it’s loads of fun!!
http://www.marknolan.com Nolan

When my kids were babies and one of them woke up at night I would rock him or her in a rocking chair and sing in low voice. It worked like a charm. My guess is it is similar to the motion and sound combo that makes kids fall asleep when you drive around in a car. But they love to have you hug them and to hear your voice even better. So try a rocking chair, and practice that singing so you don’t drive your wife crazy, ha ha.
http://www.marknolan.com Nolan

When my kids were babies and one of them woke up at night I would rock him or her in a rocking chair and sing in low voice. It worked like a charm. My guess is it is similar to the motion and sound combo that makes kids fall asleep when you drive around in a car. But they love to have you hug them and to hear your voice even better. So try a rocking chair, and practice that singing so you don’t drive your wife crazy, ha ha.
http://www.anicechat.net/ Ragnar

Aww, cute kids.

I can understand it’s painful starting up new businesses, but in some cases it results in great wealth — so it’s pretty exciting too.

The fear of nightmares is what is keeping me away from sleep.
http://www.anicechat.net/ Ragnar

Aww, cute kids.

I can understand it’s painful starting up new businesses, but in some cases it results in great wealth — so it’s pretty exciting too.

The fear of nightmares is what is keeping me away from sleep.

About Ben Yoskovitz

I recently joined GoInstant as VP Product. GoInstant changes how we use the web, making it shareable like never before.

I'm also a Founding Partner at Year One Labs, an early stage accelerator in Montreal. Previously I founded Standout Jobs (and sold it). I'm a hands-on startup guy, helping companies grow successfully from the idea forward. You can reach me at byosko at gmail dot com.

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5 Things That Keep Me Awake At Night

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So why do it?

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

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