by • April 18, 2014 • FoundersComments (11)1571

“That’s because you’re still failing”

A few months back (and a few wines deep) I was at a dinner party talking to two founders–husband and wife–who had each built big companies across a range of industries. They were reflecting on how hard startups can be on the family. I was just drunk enough to think I had something to brag about, so I mentioned how easy I was finding it to manage my work/life balance. He laughed and said:

Well, yeah. That’s because you’re still failing.

Say again?

Look, it’s easy to stop working for the night when the business isn’t going anywhere. But try going home when it means you’ll be dropping the ball on a ten million dollar deal. Startups don’t take over your life until they start really succeeding.

As if fate was determined to further chastise me, I’ve had some mighty stressful months since then, even with a tiny team and only marginal success. But instead of bumming me out, his comments made me want to double-down on figuring out how to relax. And not just personally, but as an organisation (I’ve known some founders who lighten their load by punishing everyone else in the company, and that’s not what I wanted).

After all, if we can expect life to get worse as business gets better, then it’s even more critical to lay the right foundations, processes, and boundaries while the business is still small and we have that luxury.

You can see the same logical fallacy on a smaller scale whenever a team is fund-raising or closing their first major client. They’ll say something like:

Things are crazy now and we’re killing ourselves, but once we close this deal, we can all finally relax.

But they never can. As soon as the deal closes, life gets even crazier. In fact, this has got to be one of the greatest lies in the startup world. If you’re frantic now, having more money and momentum only multiplies the chaos.

I may be very wrong about the conclusion I’m about to draw; I haven’t seen the lifecycle of enough companies to know with confidence. But I do have the strong suspicion that being at the end of your rope in the early days is a warning sign rather than a virtue. Wearing out the founders and the team is a sort of “process debt” (like technical debt). It can give you a boost in the short term, but it needs to be dealt before you grow too big or the whole machine grinds to a halt.

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11 Responses to “That’s because you’re still failing”

  1. Amy Hoy says:

    Yes to doubling down on figuring out how to relax. No to the mindset that it gets worse as business gets “better.”

    It’s like having kids:

    Some parents will gleefully warn you about how terrible it is and act like martyrs all the time.

    And the other parents choose not to stress out about normal stuff, to design a life where the “OMG sooooo stressful!” things don’t matter.

    If you’ve only seen the former type of parent, you naturally assume that That’s Just Parenting. No, it’s just THEIR parenting. When I finally met a bunch of adults with kids of varying ages who didn’t sweat the small stuff, I realized that everything I assumed about parenthood was wrong. But that wasn’t til I moved countries, because where I grew up, the stressful way was the only way.

    If you’re constantly stressing & overworking — and you don’t want to be — then you made a mistake or many mistakes and incorrect assumptions.

    Aside from bookkeeping, our business gets easier every time we do something that makes us more money.

    • robfitz says:

      I love that metaphor. I guess I’d extend it by saying that if you currently have one kid and are freaking out, then it’s probably worth figuring out how to have a workable life with that one before you have ten more. The trap I see people (including myself) falling into is believing that getting bigger will fix the chaos on its own.

      • Amy Hoy says:

        Agreed! If you’re freaking out about baby #1, another couple kids probably aren’t going to help.

        But what’s the saying, “Your first kid is crystal, your second is glass, your third is tupperware”? Experience with the first “one” (launch, book, hire, kid, mortgage) helps you calm down over time. That’s what I meant in my tweet about newbie-ness. When you’ve never done something before, your emotions go CRAZY, imagining the worst case scenario. Then you do it, it’s fine, and you realize: Hey, those emotions were lying to me. And you’re not so freaked next time. IF you do the work of introspection.

        Certainly, just getting “bigger” won’t make things easier. Definitely not automatically, maybe not at all. The first couple employees we hired were a terrible mistake and I had to fire them both. It sucked. I got a lot better at hiring though and now we’re at 5 and slowly growing, when we find the right people. The right hire makes things easier (again, over time, and with deliberate effort); the wrong hire certainly doesn’t.

        But mostly we focus on making more money & more impact for our customers with less effort and less stress. That’s a subtle and important distinction from “bigger.” I can acquire bigger customers, do huge sales, huge launches, etc., and unlike the guy who told you the story, I freak out less each time not more.

        By the way, I was so busy responding to the content of your essay that I forgot to say: Great essay! I disagree with that guy’s whole premise, but your writing was really a joy to read. You are a real storyteller.

  2. Iain says:

    I think that the decision to work at the expense of your personal life is taken too lightly and seen as the norm, rather than being seen as the tremendous sacrifice that it actually is.

    People *call* it a sacrifice, but it’s as if the word has lost it’s meaning. I wrote about something similar on my blog recently[1] as respects taking investment. In my personal experience it seems as though taking very early investment is something a lot of people (particularly in the tech startup scene) have come to see as normal, but it’s actually a huge sacrifice to give up ownership in your company that should only be considered when you have a clear understanding of how you’re going to get a return.

    The definition of “sacrifice” that I like best (and which I cite in my own post) comes from the book “Every Move Must Have a Purpose” by Bruce Pandolfini where he says that “A sacrifice is willingly giving up material because you have calculated that you will achieve a net gain in future moves.”

    If you make a habit of giving up material in a chess game without a reasonable expectation of regaining your advantage *within an acceptable timeframe* you will lose a lot of chess.

    The same goes for sacrificing any “material” (read: resources; ie. time, money, ownership, wellbeing etc.). You have a finite amount and a limited time within which to achieve a return before you lose the game.


    • robfitz says:

      The chess sacrifice makes it plain… I like it. We too often make the mistake of giving up something we care about for something we don’t, simply because that’s where the momentum is going. It’s like, “I have to give up my freedom to work this job, because otherwise, how will I get the money to be free?” In the investment case, I’m always pretty happy to give away the equity… the financial outcome is binary anyway. It’s the other bits that weigh heavier for me, like giving up your ability to walk away if a better opportunity comes along.

  3. There are some examples of successful start-ups that try to buck the trend of overworking. For instance, all employees at Treehouse only work 4 days a week:

    CEO Ryan Carson says: “We work a 4-day week (M-Th, 9-6) because we think that information work isn’t like manufacturing. Another hour at the MacBook won’t yield another $1,000 in profit. We believe that smart folks can get five days of work done in four days. Simple as that.”

    In my view, work/life balance is almost like any other metric in a start-up, you have to choose to focus on it to improve it. And I 100% agree with you Rob that if you don’t focus early on, you won’t get it right later on.

    • robfitz says:

      I remember reading that post — shows you how rare it is that we celebrate one good example so much! There are a few other good cases as well, but certainly not as many as we ought to have.

  4. Jeremy G says:


    Do you have Kindle version of your book, “The Mom Test”?

  5. Rosie says:

    I’ve been working towards a 21 hour work week* for a while now. It’s been 4 years since I mentally decided to work towards a goal of just working 21 hours a week and whilst I don’t make a case of tracking my time – on average I work about 20 hours a week.

    I have my own reasons for wanting to work less hours (family, freedom, time for myself and to make decisions without pressure). Anyone else will have their own reasons and priorities. The truth is that I never felt happy working so many hours before. It was only until I started working less that I felt happier and healthier. I made time to dedicate to myself and do things I feel are important for me. I do believe it has a positive effect on my business.

    Having the 21 hour guideline means I constantly question what I commit myself to. I say ‘no’ to things/projects/opportunities that put my 21 hours at risk. My time is too precious to be taken over by unnecessary stress.