When you want to quit because it’s just not worth it

I’ve been there too. It sucks.

You know most startups fail “only” because the founders stop working on them, and often, it’s because it’s emotionally draining. I don’t care who you are or how strong your ego is, you will have these moments — perhaps a continuous stream of moments — when you can’t take it anymore.

I literally cannot remember the number of times I was so overwhelmed at Smart Bear that I almost threw in the towel. Close the bank accounts, close the doors, turn off the website, bounce the email, and just stop.

Sounds dramatic, but it’s no exaggeration. You’ll hit these walls too; maybe a little commiseration will help you get through it.

Of course you expect these moments to happen at the beginning of startup life — when you’re least confident, have the worst product, and the least knowledge about your customers and the market. Jason Baptiste charted it well:

As you can see, the pain is not limited to the beginning of the venture. It’s still there three years in, despite real revenue, profitability, customers arriving everyday, and a great team.

Since that is not obvious, I’d like to share a personal story.

Four years into Smart Bear I had several employees getting paid decently (which at a bootstrapped startup is hard to do!), a product that people were buying, and we were doing around a million-a-year. Life was good!

I was working on my first true “enterprise sale.” (If you aren’t familiar with the professional mosh-pit that is enterprise sales, here’s a primer.)

I was negotiating our biggest order to date — something like $200,000. Actually “negotiating” is the wrong word because I don’t believe in price negotiation, even with enterprise sales (the one area that most people claim must include automatic discounting.)

The person with whom I was negotiating wasn’t the end user, nor the boss nor boss’s boss nor anyone in that chain of command. See, big companies have entire departments devoted to dealing with vendors like you and me, and when it comes to negotiating, these departments harbor terrorists with titles like Procurement Manager or Strategic Sourcing Manager.

I say “terrorists” because they use fear tactics to get their way, yet they have no power other than fear. Imagine the worst stereotype of a salesman — the greasy used-car type, except instead of selling you something, their job is beat a discount out of you.

Now to be fair, many vendors do take advantage of large companies — overcharging (because “They can afford it!”), or promising one thing to the users and sneaking something else into the invoice.

But mostly it’s because of the traditional enterprise sales dance, reminiscent of the lumbering mating dance of the great blue whale. The vendor asks for too much money; the client is astonished at the price. Both calmly explain that this is a deal-breaker. Then the vendor capitulates 30% but only if the client signs a three year maintenance contract (which they wanted anyway). The deal is struck.

(This tradition continues because of perverse, wasteful incentives. The vendor’s salesman likes this because sometimes he gets away with a high price which pads his commission check. The Procurement Manager likes this because he can show his superiors how much money he’s “saved” the company.)

So big companies need a Defender of Evil Vendors, I get that. But that’s not enough for these guys; it feels to me like an attack, not a parry.

This is always how the conversation would go:

PM: What kind of discount are you offering?

Me: We don’t discount; instead we put our pricing on our website so there’s no misunderstanding.

PM: Well I’m going to need some kind of discount. How about 30%?

Me: As it says on our website, we don’t discount.

PM: But I’m buying 400 seats!

Me: Yes, and we already provide a nice discount for bulk orders, which is already included on the invoice and documented on the website.

PM: You don’t understand, I always get a discount. I’ve done business with 47 other vendors and all of them give me at least 20% off.

Me: There’s always a first!

So far it’s actually OK — I’m the one refusing to plod through the mating ceremony, wanting to skip right to the wedding night. I expect push-back.

But here’s where it gets nasty. I remember sitting there on the phone getting lambasted for my intolerable ignorance about the Way It Works. I was told I have no business selling anything to anyone.” My obstinant ignorance is a deal-breaker because of what it implies about my company in general — after all if I don’t even understand the purchasing process there’s no chance in hell my software’s going to work! Furthermore, despite my ignorance I’m unwilling to listen to the rules, to learn, which means there’s no hope for me.

I’ll never forget how this ended:

PM: OK that’s it, you give me no choice. I absolutely cannot approve this deal, and furthermore I’m recommending that we never work with your company in any capacity. At this point, even if you gave me a discount I would still reject it.

Here’s where I’m supposed to unleash my intellectual fortitude. I won’t capitulate, will I?  I won’t let this guy insult and bully me, will I? C’mon, I’m the strong-willed confident entrepreneur with the stoic well-argued voice of reason, and he’s the sleezeball with the tedious day-job — surely I’ll laugh as his words roll off me like water off an oiled duck’s back.

Just the opposite. I felt like throwing up. He’s right, who do I think I am? I’m a geek playing in the big boy’s house and I don’t know what the hell I’m doing. I have these naïve ideas about how the world should work and how people should treat one another, and that’s just silly. And it shows. And now this guy is going back and spewing vitriol at the other folks in the company whom I actually like and worked really hard to earn their trust.

But it’s over. They’ve seen through me. It’s just a matter of time before others do too. That’s the end of deals like this.

Why am I doing this anyway? This is supposed to be fun and fulfilling but at this moment as we say in Texas I feel like ten tons of shit in a two-ton bag. What I like is writing code — why am I even trying to play this sales game? Why not just go get a job where I only worry about whether or not I can write code — because I sure as hell can do that — and let the natural salesmen do all this crap?

Is the money worth it? What money, we’re still bootstrapping and I still don’t get a regular salary. Is the promise of money worth it? Worth these feelings of inadequacy?

After days (yep, days) of fretting like this, it converted from despair to anger. Who the hell is this guy? Some asshole who isn’t good enough with money to be an accountant, too slimy to sell cars, this guy whose only skill is to be a jerk, some guy who has never had to make payroll or take a risk or put himself out there, this schmuck is going to tell me I’m the one who isn’t good enough, I’m the one who has no business selling software?

Worst of all, I’m letting him make me feel like a pile of shit!

Well if you’re waiting for the big moment where intellectual reasoning finally defeats weak, irrational emotions, I’m sorry to disappoint you, because that moment never came. I know it’s dumb and illogical, but there it is. It’s trivial and baseless but I still carry that experience in a corner of my thoughts. That’s how emotions work.

By the way, this guy turned out to be totally full of shit. Had had, in fact, no power to stop the deal. When I finally got my main contact from that company on a conference call with the PM, the conversation was literally:

My Guy: So, what’s holding up procurement’s approval?

PM: Nothing, just some paperwork, we’ll have it done by Friday.

All of that angst for nothing. Son of a bitch!

Years later I was on site at this company and I finally met this guy face to face.

I still felt small.

Want to say I’m weak?  Or he’s strong?

Who cares, the point is: Getting through this slog of a thing that’s a startup — or anything difficult and worthwhile — doesn’t require that you’re always confident or stoic or smart or right or wise. You don’t need to match the emotional stability you see from the big bloggers. (Which is mostly a façade anyway.)

It’s about sticking through the tough parts, whatever your personal foibles or weaknesses.

Living through it, not beating it. I never have, to this day, “beaten” that PM, not emotionally, not if I’m being truly honest.

I’m not saying tenacity is all it takes. Just that without it, you’ll stop. It’s so easy to stop. There’s so many reasons to stop.

And that — stopping — is how most little startups actually fail.

Let’s continue the mutual therapy in the comments. How do you deal with those dark days when you just want to stop? Do you have a story of sticking through it… or not?

89 responses to “When you want to quit because it’s just not worth it”

  1. I’m actually going through the same situation and well… I quit. It was not my startup but it was very uninspiring to see the founder not working even a 10th of what I was, as well as, being shut down by the HIPPOs; seeing my colleagues working as hard as I did and being very underappreciated. This founder has no leadership whatsoever and thinks being the leader of a team is telling them what to do and taking the credit for it. No hard work implied.

    If your team doesn’t see you setting an example for hard work -as a founder or team leader- don’t expect them to listen to you or come to work motivated to create great things. It simply won’t happen.

  2. “I’m a geek playing in the big boy’s house and I don’t know what the hell I’m doing”
    I think I hit this one every other week. Add a cold and new bug and things feel awful shaky; but then the bug gets fixed, somebody says “hey, that looks cool” and BAM! back on top of the world… for a few days at least. What a ride – thanks for sharing another helpful tale!
    Looking forward to your session at SXSW too btw.

  3. Thanks for the awesome post!

    Such moments are all the more common if you are dealing with an industry where you are mostly an outsider. It is hard to know whether the other person is simply being mean or you really are way off the mark.

    In my startup, this resulted in we preferring to deal with individual customers as opposed to business customers. But I know that one of these days we have to bite the bullet and start going after them.

  4. Hey, I didn’t see comments yet, so thought I’d break the ice. No useful tips, but in every job there’s the pain and that moment. (In my job, I’m a vendor, and buy from vendors, and have internal clients…so some days it’s all good, some days it’s all painful.) Hang in there — and thanks for posting this, it made me feel less alone when I have those kinda days. ;-)

  5. Great article — both in terms of the general message and the specific story about the bully.

    One thing that helps a lot in a situation like that is having advisors (or board members) you can trust to talk with in situations like this. If they all also say “you don’t know the Way It Works”, then it’s worth listening. More likely, though, they’ll say something more along the lines of “Wow, that guy’s an asshole. Look, you’re confident about your business model, and here are some other examples of companies who don’t offer bulk discounts. He’s just being a roadblock. Here are some sales techniques that might help in a situation like this.”

    At my startup back in the 1990s, we had gotten to verbal agreement on a $200K deal. The paperwork hit a snag and our CEO headed off on vacation to a place with no FAXes or FedEx, but no problem: I was a naiveish techie, but I wa also founder/CTO and had signing authority. So we agreed that I’d fly to their location onsite, sign the contract, and get going. Once I got there, surprise: a couple of new terms! And no, we couldn’t get started without a contract.

    I said, y’know, I’m not comfortable with this. They said “but that means you’ll just have to turn around and fly home.” The deal was pretty key to our success and I didn’t want to let it go but you have to draw lines. So I called up one of my board members, who agreed. They said “stick around for lunch, let’s talk this through.” After lunch they decided that the new terms didn’t have to be there after all. Funny how that worked.

  6. Did Jason Baptiste draw that graph? I thought Paul Graham did at the YC offices. (The one with the Tech Crunch of initiation)

  7. Four Excedrin headaches:

    (1) Company has some very expensive equipment that makes heavy use of hydraulics and, thus, hydraulic fluid.

    In the maintenance shop, the master supply of hydraulic fluid is kept in its own barrel, with its own special color and big labels about its crucial contents.

    Someone notices that somehow the barrel of hydraulic fluid has oil in it instead.

    Now, how many pieces of equipment had that sewage added to their hydraulic systems?

    What to do about that?

    (2) Somehow a union didn’t like some of the operations and showed up with guns.

    (3) For the equipment with the hydraulics, someone believed that they were owed money so sent a Sheriff to take the equipment. So, hide the equipment until the Sheriff left!

    (4) Customers are really happy with the service, but billing is way behind. There are paper forms in stacks in the halls, on both sides, with the stacks wide enough that can pass the hall only one person at a time, walking sideways.

    The customers call and say that until you bill us and let us pay what we owe, we’re not going to use your service again.

    Lesson: Supposed to expect some such disasters and have a little wiggle room in the planning to handle them! Don’t grow so fast that run out of wiggle room.

  8. What an inspiring article. I’m keeping this for myself and sharing it to friends who are also geeks playing in the big boy’s’ house.

  9. Four years ago two major competitors were spending money like crazy and expanding staff. They took VC money and had every #1 adword position was industry keywords. I kept thinking to myself that I must be the one doing something wrong. Why didn’t I hire 100 more people in 12 months to build software that I had built with a team of 3? Why wasn’t I spending tens of thousands per month on Adwords? I wanted to hang it up at that point. Why go on?

    Fast forward to today. Both competitors were spending far more than they could ever hope to recoup. Both went bankrupt and were sold off at fire sale prices. It was an important lesson to not judge my performance by the appearance of competitors.

  10. Here’s what I do as I am entering my third year since the conception of Sharing Profiles.

    I call it a day, go to bed early, and try to get a good night’s sleep. I then get up in the morning, stretch and/or mediate, put on yet another pot of coffee and work yet another 16 hour day…..

    It boild down to belief and failure NOT being an option. I believe that these “foundation-laying” years will pay off. Period.

    BTW: Gotta love this quote: “Is the promise of money worth it? ”

  11. I was going to qualify my initial statement with: ” …as technology solutions become less and less proprietary..”

    No need. Universals need no qualification.

    You get the same from enterprise legal departments. The larger an organization becomes, the more obstacles in the sales channel. Even if you have contacts that the White House would envy, and every engagement is selling to VITO, you’re invariably demoted to months of correspondence with those within the organization that are exclusively devoted to seeing the world from a place of liability as opposed to opportunity. It’s the cost of doing business with behemoth, clunky Leviathans.

    It’s a shame too because market velocity could use the acceleration as opposed to the brake.

    To your point regarding pricing strategy for enterprise, for the sole reason stated above, I agree with you 100%. In fact, if you back out the opportunity cost devoted to pandering to legal, sourcing, procurement, and IT, the pricing strategy specific to enterprise should be reversed. (Parenthetically, I should add that for those product and service solutions that target SMB, the grass is not always greener for your brethren selling into enterprise.)

    Great post, per the usual. Timely, too. Hope you’re well.

  12. Excellent post. Calls to mind the line from Yeats: “The best lack all conviction, while the worst/Are full of passionate intensity.”

  13. Wow! And just when I was feeling so alone… Putting fun aside, you’ve hit surely a sore point. Being a startup should be equal to endless fun, energy and fulfillment in general. Not so. But, pray, do not tell anyone! You might have failed… Those days you describe are there. And mostly there for a reason. I have finally harnessed them into a believe: they’re there to get you back in shape. Get your anger, your passion, your drive, love, your whatever back. But, indeed, there is no circumventing the truth of feeling down as hell at times.

    On the bright side: I’ve felt that getting out there is just the right medicine. Even though business won’t let you. Even though you’ve still got ten dozens projects to do and errands to run. Even though you’ve many other excuses. Just take the dogs for a walk. Make yourself do it. M-a-k-e y-o-u-r-s-e-l-f d-o i-t. Walk on and on and on. Just until you finally feel the chill of the wind tickle your spine and the warmth of the sun in your face. Just that and nothing else.

    Then I’m ready to go again.

    Good job, Jason! First time I’ve commented on all those posts you’ve written to ‘me’. Keep me going strong, man!

  14. Excellent post Jason: As a sales guy (and coach), I always advise clients to go with a “No Haggle” pricing model. In this way, you can present pricing as a service to your customer rather than as an invitation to do battle.

    The important thing is to fully understand (and to be able to clearly describe) the rationale for your pricing model. In response to demands that I lower my price, I use these strategies:

    1. I know what “reasonable” profit margins are in my industry – and I adhere to them in my pricing. Anyone asking me to discount is making a de-facto unreasonable request.

    2. Sure, some companies will charge less, and make less. But what happens to companies that consistently underperform the market? They get sold and busted up. They go out of business. They limp along for years cutting corners. None of these outcomes serves their customers’ interests.

    3. If my final price is a bit higher than the competition, I can justify it. I will use known ROIs, descriptions of my world-class development/support teams…and even the fact that we’ve just got “cooler” stuff. Just ask Steve Jobs.

  15. Startups are definitely emotionally draining, and while I would like to believe in my resiliency, if I didn’t have two awesome co-founders there in the trenches with me, I’m not sure I’d still be fighting the good fight (Thanks Ricky and Mark!).

    I can’t seem to find all of the details about Smart Bear, but it sounds like it was a bootstrapped, solo founder operation (not sure how quickly you hired those 4 people). That amazes the hell out of me. Solo founders in general seem like magical Django ponies with how they’re able to juggle and prioritize product, customers, etc. But the hardest part of being a solo founder must be not having the emotional support of knowing that there are people there on your team working till all hours of the morning right here with you. I know Ray of Ginzametrics has said that his family is a huge help almost to the point where his wife is almost like a cofounder – how did you get through the tough times, Jason?

  16. I’d posted this in a thread on Hacker News, but feel compelled to put it up here again:

    We built a decent product in around 6 months, and began engaging with enterprise customers. 6 frustrating months of trade shows / cold calls / presentations later, we had a couple of potential customers but things seemed way too stagnant; their intent to purchase just wasn’t apparent.

    We’d been through negotiations, product iterations, feature requests and what have you. Low on cash, the first visible cracks in our patience were emerging, but we stayed put. And that’s probably because we’ve known each other for over 5 years and each of us didn’t want to let the others in the team down.

    And then suddenly a month later we received our first purchase order. Okay, it wasn’t exactly sudden – we’d followed up a million times with the client and iterated on the product each and every time. But nothing else had changed, we hadn’t done anything significantly different in that one month. And that had us convinced that patience, or should I say dogged resolve can be a real virtue.

    We’ve gotten decent traction since and a repeat order as well as a testimonial from our first customer to boot. Here’s the a link to the testimonial [PDF]:


  17. As one of the two devs at the startup I work for, I cannot take it anymore. The financial pressure is killing me and I have to walk away before I snap.

    It feels horrible. I’ve put much sweat and tears into this product over the past year, but at some point, you have to do a reality check. The car wreck was what did it (fortunately a minor fender bender) – I absolutely cannot afford to replace my car on my own and neither can the startup, if it had been *any* worse. God forbid there were medical bills involved.

    I feel bad for having to leave and would happily work there again if things were slightly improved.

    So there’s the flipside. Sometimes you don’t have a choice.

    • It’s sad to walk away of course, but it takes guts and introspection to realize it’s the right choice, whether it’s the choice you wanted or not.

      There’s always another idea, another opportunity, another time. Cheers.

    • It is totally different work “for” someone else and “for” the goal..If everyone on the team is not treated equally, then yes, time to leave and start your own.

    • It is totally different work “for” someone else and “for” the goal..If everyone on the team is not treated equally, then yes, time to leave and start your own.

      • It’s not about treatment – I am, unfortunately, an indispensable part of the team, as the founder has said on several occasions. I am not treated better or worse than anyone else, thankfully.

        But there’s a part to the startup that I learned thru experience, which is, make sure you have all your ducks in row going in. Technically, I think my kung-fu was in order. Financially, no savings and not much else, either, was not a good way to start.

        I doubt I’d do anything different, except to ensure that I had no overhanging debt going into it.

  18. A huge problem that I have is that I have trouble in negotiations asking for my fair share. I usually get bullied into accepting a crappy deal. Which is why I decided that I was just not going to negotiate with anybody. I suck at it so bad that in the long run I would probably loose. I decided that instead I would implement fixed prices. Also, i decided not to partner with anybody, I’m your solo programmer selling in the iphone and android appsores. I’m glad to know that I’m not the only one that feels tiny compare everybody else.

  19. I can empathize, great post! The dark days sometimes make you feel like an idiot and you just want an exit in anyway possible, but then some ray of hope comes along. Maybe it’s journalist writing about you, a user sending you an email of encouragement or a stranger commenting on how great your site is. Sometimes even the smallest bit of encouragement can go a long way.

  20. Great post Jason, I always thought that I wouldn’t have to deal with these kinds of people as an owner but as you know assholes exist everywhere — then they try to become your customer.

  21. love the story, and i can commiserate. however, lesson learned. for any company that has been “institutionalized”–meaning more than 1000 employees, you have to raise your price by 30% before you show it to them, then when they ask for the discount, you can give it to them. all part of the stupid idiotic institutionalized dance they do. but at least now you know the steps. ha!

    i quit on a startup after 3 years, and it was agony. pure hellfire suffering and gnashing of teeth. we hit one landmine after another and didn’t make a cent.

  22. Great post… raw and truthful. A great read, also appreciate you being willing to dig deep to write all this up given the “startup writing” game is mostly about how smart and awesome I am and how I wheel and deal with the big-dogs and am so amazing that everyone should follow me on twitter until their eyes bleed.

    Gets really old (and smelling of BS) when that is all I read; really enjoyed how real this post was instead.

  23. I’ve worked for two bubble companies and three major (Fortune 100) companies as a buyer of technology and the other side of this is the debate the buyer (the protector of evil vendors) has to go through for any vendor. I can give you an example in photo and video compression that was in Russia. By far the best compression I had seen at the time (2002 or so) yet the company I worked for (large camera company) wanted their technology in what amounted to free. I worked so so hard to get them to see that this technology was light years ahead of very one else but didn’t matter we are ….. and we get everything for this price. Great article.

  24. Such a great article! My partner and I haven’t had a vacation since 2009 and I will freely admit to having a few days (weeks?) where I wanted to crawl back into bed and hide under the covers in the fetal position. Our company is not sales driven in the traditional sense, but we are bootstrapped and have done everything with just the two of us. When it comes to relying on your own resources it’s very easy to get into the habit of never taking a break. I come from a long line of workaholics but have learned that burnout WILL find you, and burnout makes everything that much harder. Challenges seem bigger than they are, accomplishments seem smaller. It really is easy to have those moments where you feel defeated. One of the things that got me through the earlier part of development was training for a marathon. It forced me to get out of the office, and most importantly gave me definable goals that I could reach on a weekly basis. Starting a company, especially one that involves code development, can be difficult because it’s not always easy to set goals. Things you think should take a week end up taking a month, one side of the website breaks when you fix the other side, etc. That being said, the feeling of accomplishment that comes with slogging through the challenges and emerging on the other side is entirely awesome and worth it.

    Love this quote…”You don’t need to match the emotional stability you see from the big bloggers.” That’s right, let your little (sometimes hiding under the covers) company flag fly.

    Thanks for the post!

  25. If you think that’s fun, try selling stuff to a government agency! You combine the “strategic sourcing” nonsense, with byzantine layers of contracts, people you need to hit quotas for various demographic categories and bizarro laws.

    Some states have default terms like “Product must not contain Amazon hardwoods” or “Sign this waiver that you don’t discriminate against Catholics in Northern Ireland”.

  26. As the saying goes “the highs are really high…and the lows are really low”.

    We had been pursuing a customer meeting for a few months. Within 2 days, we got a confirmed meeting (our first big break)…and my main developer resigned. Yes, it was a emotional roller coaster… HIGH and LOW in 48 hours. We pulled it together and got another person on board, but at the time, not continuing was something I considered.

    Then you get up the next day…and say, lets keep going. Good post Jason.

  27. As the saying goes “the highs are really high…and the lows are really low”.

    We had been pursuing a customer meeting for a few months. Within 2 days, we got a confirmed meeting (our first big break)…and my main developer resigned. Yes, it was a emotional roller coaster… HIGH and LOW in 48 hours. We pulled it together and got another person on board, but at the time, not continuing was something I considered.

    Then you get up the next day…and say, lets keep going. Good post Jason.

  28. Yes, startups are both emotionally and physically draining and that is why not everyone can start or work at a startup. The way I deal with dark days is by accepting and convincing myself that bad days are necessary to achieve success.

    One thing that always helps me is understanding that there are somethings I can’t control, and because of it there is no reason for me to stress over these things. I try to concentrate in the day I am living and not so much in the past or future… if I do alright today, I’d probably be OK tomorrow ;)

    TIP: I know it sounds silly, but every time I feel down I remember that moment in the movie Jerry Maguire where he is singing in the car… “Yeah I’m free, free fallin’”; laughing at yourself works too ;)

  29. N.B. The figure is actually a photograph of the Y Combinator whiteboard showing a chart made during the Winter ’08 round. If I recall correctly, Paul Graham and Trevor Blackwell were the main instigators, but several other people contributed as well.

  30. How do you deal with those dark days when you just want to stop?

    I sit, close my eyes and remember what it was like to get up at 5:30 Mon-Fri to be at work by 7:30, shuffle some papers, go to a meeting, then lunch and come back, make a few calls in the afternoon and try and get out at 4:50 to “beat the traffic” and make it home by 6:00 to shower and dress for the evening, eat dinner around 7, work on my side project from around 8-10… crash and do it all over again tomorrow.

    Do you have a story of sticking through it?

    Sued in my first 60 days!

    I started the company in March 2005, bootstrapped and on my own as a solo founder. In May 2005 I was served papers (on my birthday no doubt) in an attempt to get me to cease & desist immediately. Basically the courts halted my business until a jury could decide the outcome, (legal maneuver meant to bleed me dry). The David vs Goliath case dragged on for 18 months or more, before the prosecutors sent a letter of settlement the day of our trial.

    The letter stated we couldn’t sue them and they couldn’t sue us for the same things ever again, but we both had to pay our own legal expenses. This cost me upwards of $20,000.00 in my first 90 days with no paycheck on the horizon – I was day to day and running on empty.

    Having survived this fiasco I got to work on creating a revolutionary process for my industry so much so that I had it patented, READ: another $5,000 and a 2-year process.

    The idea is to have a map of where you want to be and when you want to be there and stay focused on that journey. I’m still a solo-founder, can’t get the right co-founder (Jason). I have a 3 year agreement with a Fortune 100 worth 200-400K per year and yet everyday is still a struggle .

    The alternative: a 40 hour-a-week job working for someone else. That’s what keeps me motivated and excited about what I’m doing.

    • That would be an incredibly valuable product for me… I am now realizing that one, perhaps the big reason, I have trouble keeping motivated and ontrack is scale vs. scope… people estimate most things linearly but the world works on a log scale.

      A simple example… how far is the horizon? No way to know…it a logarithmic distance. How far away is the nearest wall? Easy… linear… mental ruler comes out, 6 ft.

      So what happens? People vastly underestimate what’s not in sight. How much? Log scale gives real meaning (not precision) to that… no way to know all the fallout that choices can incur.

    • That alternative is pretty terrible. Much better to be sued indefinitely and choose to do something meaningful and self directed.

      The issue is surviving long enough to stand on your own, congratulations to making it through an additional legal mess. Enduring just a few more days, and looking forward to full days of “side projects”.

  31. Holy f-ing A Jason…there is so much wisdom here that a long reply is due, but a short one will have to suffice..Yes, when you are doing something you KNOW is right, self-doubt is the worst enemy in the room…As Farragut said, “Damn the torpedoes!” Do not sink your own ship! Thanks for this post friend.

  32. You just have to plough through. Plough through your own fears and plough through other people’s bullshit.

    Thanks for this honest and personal account. Cheers!

  33. Wow, I’m going through the same situation this very moment with my start up. Good to hear the humble succeed!

  34. I get a similar feeling of intimidation just from monitoring the rss feeds of sites like HackerNews, TC, Mashable, etc.

    I like to think of myself as a pretty sharp guy i.e. knowledgeable about what it takes to run a successful small business. Reading many of the articles along with the corresponding comments can not only make a guy feel intellectually inadequate, but that he has a LOT more to learn. There are some really BRIGHT people out there, some of which will ultimately be my competitors.

    Fortunately I dont think I’ve ever come to the brink of throwing in the towel on this basis alone.

    • I share that and am also grateful to now have that perspective beforehand… fantastic to see some of the other ponds and caliber of fish therein.

  35. It’s people like the PM you describe that have hallowed out our manufacturing base. After so many years of forcing ‘discounts’ from suppliers, the suppliers either died or moved overseas. I used to watch it as an engineer at one of the big auto companies. We’d work with suppliers for months/years and design the parts/system to be as efficient and economical as possible. Then a PM would come in at the end and demand price reductions, when they had no clue what the costs should be.

    The sad thing is that we’re at the point where the PMs have slit their own throats because their job have gone now too. First it was the manufacturing, then the engineering, then the middle management, and eventually everything is done elsewhere. People forget that Henry Ford didn’t pay his workers $5 a day because he was generous. He realized that they would be his best customers if they had money.

    Great post.

  36. Version control systems have made it possible for habitual quitters like me to go back a year or more later and continue neglected projects. I always get caught up with my full time job and leave side projects in a dusty closet. One day I’m hoping one of these side projects will find the promised land but it is very tough with all this quitting!

  37. Hi, after 30 years of self employment – I can only add this comment. When you hit a wall of pain and really feel that the load has become to heavy, simply change something.
    Now this could be a massive change – or a tiny one , like starting earlier every day, or adding an outside interest like going swimming at lunch time, and the effect is likely to be instant. Perhaps completely moving your entire store to a new location…
    I used to work on the craft markets as one of my business sources – and eventually the discount mentality did get to me, so I simply changed my methods of marketing.
    Hang in there – it really is worth it!

  38. I read a lot of blogs. This one is more genuine and more helpful than 99% of all other “advice” posts I have read. And I really appreciate the fact that you don’t cling to some sort of entrepreneur hubris that vision will defeat all other negative emotions

  39. “Well if you’re waiting for the big moment where intellectual reasoning finally defeats weak, irrational emotions, I’m sorry to disappoint you, because that moment never came.”

    How can it ever? I frankly don’t know of a single philo-intellectual-1600-SAT-wunderkind who manifested that IQ prowess to happiness. When they tell me how incredible Atlas Shrugged is I always ask them if it made them happier? LOL!


  40. Great post and really insightful, interesting comments. So much of what you’ve written here rings true and reminds me of thoughts I’ve had myself, time and time again. Feeling like you are out of your league and that you’ll be “found out”…who hasn’t experienced that before? If you try to build something great, I think it is impossible to avoid having moments where you are in too deep and need to learn how to swim very, very quickly. This really hits home and certainly helps me feel a bit less crazy.

    The one thing I would ass is that sometimes the opposite is just as important – are you sticking by for the wrong reasons? I’ve certainly seen, and been a source of, actions that are ultimately being driven more by competitiveness or vengeance than by sticking to one’s principals or trying to do the best thing for a team or company. I’ve gotten much better about this over the years, but I am not a stranger to staking out a ridiculous position and defending it to the point of absurdity, particularly about meaningless product features or aspects of a deal. Have the courage of your convictions, but know when it has nothing to do with your convictions at all.

  41. I have been in the apparel business for 25 years, and the owner of a “start up” for 5 years.
    You have to have integrity in your pricing structure: That is the only way that you can know that you are doing the right thing (we have a saying in apparel, and its very crude and I apologize but its apt, “…once a wh*re always a wh*re…”). Sometimes the best thing you can do is walk away from a losing proposition and its hard, very hard to do…I know. I don’t look at it as having to “beat” a PM or in our industry, a buyer, I actually take the perpective of I have not educated them well enough because I realize that it is a small world and you would be surprised how many times people seem to pop back into your world.

    As far as quitting…sometimes you just have to accept the fact that somethings are just out of your control. Right now my business has tripled and I started my company with all my own funds, but I do not have the funds to produce the inventory that I need to handle the growth and I also cannot seem to interest anyone in investing in the company. Sometimes you can have a great business and have unheard of margins but you can find yourself in an industry that does not fit what investors are accustomed to dealing with. I produce t shirts for big and tall people (fat!) and I have to admit even I realize that we look like a dinosaur amongst a group of race horses when I hear what some of my competitors are seeking investment capital for. I love what I do but I have to admit that when some of these tech start up folks share their pitch with me even I have to say, “Wow! Thats awesome!”

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