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 YoskovitzQuinn 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

  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!

June 1, 2008 Posted in Humor, Startups by

  • http://www.poptaste.com egi

    internet always keep me awake at night :)

  • http://www.poptaste.com egi

    internet always keep me awake at night :)

  • http://www.babythings4u.co.uk Peter

    Cute pictures of the kids.
    What keeps me awake at night is thinking about how to better my situation all the time.
    Somtimes I can be awake for hours thinking about how to solve business / work problems in the most efficient mannor possible.. i guess this is what happens when ur a geek :)

  • http://www.babythings4u.co.uk Peter

    Cute pictures of the kids.
    What keeps me awake at night is thinking about how to better my situation all the time.
    Somtimes I can be awake for hours thinking about how to solve business / work problems in the most efficient mannor possible.. i guess this is what happens when ur a geek :)

  • http://softdigital.blogspot.com Jimy Wong

    Hi Ben,
    First thing first, you got cute kids. Just do what you like is the best way of life.
    Peter, you need time. Be the best and slowly. Look around you, don’t ignore everything.
    All the best!!

  • http://softdigital.blogspot.com Jimy Wong

    Hi Ben,
    First thing first, you got cute kids. Just do what you like is the best way of life.
    Peter, you need time. Be the best and slowly. Look around you, don’t ignore everything.
    All the best!!

  • Chad Gary – Youth Organization

    My laptop keeps me awake at night. Very difficult to put it down sometimes.

  • Chad Gary – Youth Organization Specialist

    My laptop keeps me awake at night. Very difficult to put it down sometimes.

  • Alicia Wills

    My husband snoring keeps me up!

  • Alicia Wills

    My husband snoring keeps me up!

  • http://mouthfulofpolitics.typepad.com/ Tim

    As a father of five, I feel your pain.

    Good list, and I’d like to comment on number four. Regular exercise in some form not only keeps you healthy, but also gives you energy, which you can then apply back to your business.

    My recommendation: bicycle riding or swimming, both great aerobic activities

  • http://mouthfulofpolitics.typepad.com/ Tim

    As a father of five, I feel your pain.

    Good list, and I’d like to comment on number four. Regular exercise in some form not only keeps you healthy, but also gives you energy, which you can then apply back to your business.

    My recommendation: bicycle riding or swimming, both great aerobic activities

  • http://www.instigatorblog.com Ben Yoskovitz

    Thank you for all the comments. Seems I’ve struck a nerve with this post – and I’m far from the only one getting very little sleep at night!

  • http://www.instigatorblog.com Ben Yoskovitz

    Thank you for all the comments. Seems I’ve struck a nerve with this post – and I’m far from the only one getting very little sleep at night!

  • http://virtualbuzzassistant.com Ron McDaniel

    Don’t worry Ben, it gets better between 7 and 9 – then they get hard to deal with again. :)

    Commenting on your Quick vs Rash comment – I just started a new endevor – http://virtualbuzzassistant.com – and I am coaching people though starting their own Virtual Buzz Assistant business. One person got completely hung up for over a week on whether they should open a PO Box first or file the papers for their LLC first.

    My advice to him was to accept that you will make mistakes, but most mistakes are better than wasting too much time trying not to make any mistakes. Fail forward.

  • http://virtualbuzzassistant.com Ron McDaniel

    Don’t worry Ben, it gets better between 7 and 9 – then they get hard to deal with again. :)

    Commenting on your Quick vs Rash comment – I just started a new endevor – http://virtualbuzzassistant.com – and I am coaching people though starting their own Virtual Buzz Assistant business. One person got completely hung up for over a week on whether they should open a PO Box first or file the papers for their LLC first.

    My advice to him was to accept that you will make mistakes, but most mistakes are better than wasting too much time trying not to make any mistakes. Fail forward.

  • http://niagarumah.com Rumah Dijual

    I think my insomnia keeps me awake at night. That’s terrible.

  • http://asianjobcenter.com Immer

    I think my insomnia keeps me awake at night. That’s terrible.

  • http://www.dataplus-svc.com Bonnie

    Hi Ben,

    Totally understand. Been there, done that! It will get better, then it will get worse. Mine are grown and married. I miss staying up all night with them.

    Enjoy while you have them.

  • http://www.dataplus-svc.com Bonnie

    Hi Ben,

    Totally understand. Been there, done that! It will get better, then it will get worse. Mine are grown and married. I miss staying up all night with them.

    Enjoy while you have them.

  • http://www.orlando-real-estate.biz Chantal

    You are so spot on with hiring good staff. After having five start up companies (some huge successes others miserable failures), I can honestly tell you that there is no better day than the day you realize you can go to lunch or take a day off and everything is running smoothly and money is flowing in the door.

    Your staff are what differentiates you from being a manager or a supervisor (baby sitter).

  • http://www.orlando-real-estate.biz Chantal

    You are so spot on with hiring good staff. After having five start up companies (some huge successes others miserable failures), I can honestly tell you that there is no better day than the day you realize you can go to lunch or take a day off and everything is running smoothly and money is flowing in the door.

    Your staff are what differentiates you from being a manager or a supervisor (baby sitter).

  • http://www.thesolutionwebsite.com AJ James

    1 thing that keeps me up at night is whatever my wife says before I go to sleep.

    She has a happy knack for dropping big news right before she falls sound asleep, leaving me wide awake and panicking.

    “goodnight honey, by the way I’m pregnant” – Snooze zzzzz

    “I think we should move to New Zealand” – Snooze zzzz

  • http://www.thesolutionwebsite.com AJ James

    1 thing that keeps me up at night is whatever my wife says before I go to sleep.

    She has a happy knack for dropping big news right before she falls sound asleep, leaving me wide awake and panicking.

    “goodnight honey, by the way I’m pregnant” – Snooze zzzzz

    “I think we should move to New Zealand” – Snooze zzzz

  • http://www.dataplus-svc.com Bonnie

    Keeping my employees busy – keeping enough work coming in!

  • http://www.dataplus-svc.com Bonnie

    Keeping my employees busy – keeping enough work coming in!

  • http://www.yardsmartlawncare.com DJ Carroll

    I love the point about the rash decisions vs quick decisions.

    I am in my second year of running yard smart lawn care & landscaping and let me tell ya its tough trying to be mr nice and mr right all the time along with mr get it done

    Great PosT!

  • http://www.yardsmartlawncare.com DJ Carroll

    I love the point about the rash decisions vs quick decisions.

    I am in my second year of running yard smart lawn care & landscaping and let me tell ya its tough trying to be mr nice and mr right all the time along with mr get it done

    Great PosT!

  • http://www.infomercialscams.com/scams/direct_buy_scams/start/000000000000 Kristin

    Okay, so this is my first time visiting your blog, so hello! I randomly came across it and I really enjoy your writing. The pictures of your family are so cute.

    I’ve been working on starting my own business, and wow, I am always up all night too. haha

  • http://www.infomercialscams.com/scams/direct_buy_scams/start/000000000000 Kristin

    Okay, so this is my first time visiting your blog, so hello! I randomly came across it and I really enjoy your writing. The pictures of your family are so cute.

    I’ve been working on starting my own business, and wow, I am always up all night too. haha

  • http://morganwrites.worpress.com MorganLighter

    Ben, you want to know what keeps me awake at night?
    Kids -no. Barking dogs – no. Indigestion – no. Prostate problems – no. My wife snoring – no.
    It’s wondering how I could ever become as smart as you!

  • http://morganwrites.worpress.com MorganLighter

    Ben, you want to know what keeps me awake at night?
    Kids -no. Barking dogs – no. Indigestion – no. Prostate problems – no. My wife snoring – no.
    It’s wondering how I could ever become as smart as you!

  • http://www.rickety.us Rick

    What keeps me up at night? For the last ten months – nothing. Prior to that about anything would keep me awake. Just thinking and worrying some. Then I decided to slow down, let some projects sit, not argue, and just be more laid back. Result? I fall asleep within fifteen minutes and if something wakes me I go right back to sleep, I don’t set an alarm anymore yet I still wake up when I need to.

  • http://www.rickety.us Rick

    What keeps me up at night? For the last ten months – nothing. Prior to that about anything would keep me awake. Just thinking and worrying some. Then I decided to slow down, let some projects sit, not argue, and just be more laid back. Result? I fall asleep within fifteen minutes and if something wakes me I go right back to sleep, I don’t set an alarm anymore yet I still wake up when I need to.

  • http://www.msnpaketi.com Msn Avatarlar?

    thank you very much.

  • http://cigarest.mb16.com Martin

    I can't work during the day so basically I only live during the night… this keeps me up..

  • http://cigarest.mb16.com Martin

    I can't work during the day so basically I only live during the night… this keeps me up..

  • http://cigarest.mb16.com Martin

    I can't work during the day so basically I only live during the night… this keeps me up..

  • http://www.tipstostopsnoring.com/conclusive-research-on-snoring-remedies/ Snoring Remedies

    my husband snores every night and i don’t feel bad shaking him awake to stop him. that or i have to fall asleep before he starts

  • http://www.bestforlessrx.com/ Phentermine

    Well seems like you not getting sleep has become normal to you,

    I think your right when you say that sometimes the decisions that you take can make you stay awake! Even if it is a good one!

  • http://www.thompsonoutdoors.com/b/ Murthy Rao

    when i achieve my dollar target per day I'll sleep without any worries…. Otherwise I'll awake at least thrice in a night…. now I'm earning 50$ per day…. unfortunately my target is 150$ per day…. ha ha ha….

  • http://www.thompsonoutdoors.com/b/ Murthy Rao

    when i achieve my dollar target per day I'll sleep without any worries…. Otherwise I'll awake at least thrice in a night…. now I'm earning 50$ per day…. unfortunately my target is 150$ per day…. ha ha ha….

  • http://www.thompsonoutdoors.com/b/ Murthy Rao

    when i achieve my dollar target per day I'll sleep without any worries…. Otherwise I'll awake at least thrice in a night…. now I'm earning 50$ per day…. unfortunately my target is 150$ per day…. ha ha ha….

  • http://www.thompsonoutdoors.com/b/ Murthy Rao

    when i achieve my dollar target per day I'll sleep without any worries…. Otherwise I'll awake at least thrice in a night…. now I'm earning 50$ per day…. unfortunately my target is 150$ per day…. ha ha ha….

  • http://www.thompsonoutdoors.com/b/ Murthy Rao

    when i achieve my dollar target per day I'll sleep without any worries…. Otherwise I'll awake at least thrice in a night…. now I'm earning 50$ per day…. unfortunately my target is 150$ per day…. ha ha ha….

Ben Yoskovitz
I'm VP Product at Codified (makers of VarageSale).

I'm also a Founding Partner at Year One Labs, an early stage accelerator in Montreal. Previously I founded Standout Jobs (and sold it).

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