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The Founder’s Paradox: When Thinking Big Holds You Back

While building Buffer, there have been times when things have started to go a little crazy.

It might be being featured in a big blog, seeing lots of tweets about us, or noticing a big influx of signups or upgrades. When this happens, it is very easy for my thoughts to drift off and to start thinking of the big-picture possibilities for us, long into the future.

It may be healthy to be ambitious, but often these thoughts occupy more time than they should and stop us doing the real work we need to do to get anywhere near to those thoughts becoming reality.

Here are some of my thoughts on finding the right balance when it comes to “thinking big.”

thinking big

Why do we start to “think big”?

I’ve been trying to think about why it is that these thoughts emerge especially at times when some “minor successes” occur. It seems that most of the time, it is a result of a chain of thoughts, each a step further than the previous. Before you know it, you’re thinking about how your startup is going to change the way something is done in a profound way.

It often happens when you’re with someone else and neither of you stop the chain of thoughts.

I’ve realized that part of the process of an early stage startup is to steady yourself when these occasions arise, and to stay focused on the immediate tasks such as making sure customers are happy, improving the user experience and working on upcoming features.

The startups we know today started small

It is easy to look at the success stories of the world and think they started at the top. Let’s try and question that and think how all successful ventures or entrepreneurs started with something small.

Richard Branson may be trying to bring space travel to the masses with Virgin Galactic, but he started out with a magazine called Student. Google started as something used by just a few at Stanford. Facebook started just at Harvard.


For comparison, here’s a picture of Buffer’s very first version, which also looked equally scrappy:


Focus on the next point, not the peak

The spiral of success is what you should focus on — trust that with each achievement you will be more informed and better positioned to tackle the next, slightly bigger challenge. Don’t go for space travel right away. It took Branson 38 years.

think small

My thinking here is reflected by entrepreneur turned VC Mark Suster, who conveys a similar message very eloquently in his post, Why Entrepreneurs & VCs Should Focus on Basecamp, Not the Summit.

“My goal: Basecamp.  From there we’ll figure out whether to go for the summit, whether to sell or whether to look for adjacent mountains. See, the funny thing is that when you get to basecamp 1, you often find out that there are bigger opportunities or maybe just an easier route to climb on an adjacent hill.”


Is it so bad to have ambitious thoughts?

I personally love to think big. It’s something I almost pride myself on — there is a lot I want to do, and I truly believe I will achieve it. I think it can be argued that it is healthy to have ambitious thoughts.

Perhaps depending on the type of person you are, you either think big too much or you don’t think big enough.

It is those of us who think big too much who need to pay attention to this the most. A certain amount is definitely healthy, but beyond a point it becomes a huge time sink, and could actually stop you reaching your goals.

How to steady yourself and keep moving forward

Time and time again, I’ve found myself needing to become aware of these too-big, world-changing thoughts and stop them before they stop me from moving forward.

This applies to everything, too — keeping your initial product minimal, going for smaller press before you’ve built up momentum, or even realizing you can get started without waiting for perfect conditions.

Working with others can help a lot. However, it is worth noting that one of you needs to stop those thoughts before they take up a lot of time. Inevitably the discussions start, and they’re fun, but then comes the time to get working again.

In the end, though, no one else is going to do it for you — you’ve got to stop thinking about changing the world, and do the nitty-gritty to get one step further.

I know I’ll certainly need to come back to this article to remind myself of this.

Have you experienced a similar feeling around “big thoughts”? How do you handle it? Is thinking big necessarily a bad thing to you? I’d love to hear your thoughts.

  • I think that I understand what you are saying. It’s not that big ambitious thinking is bad. Not at all. It’s just that we have to keep ourselves in check because often the idea is just so big that we don’t even attempt to start it. I am guilty of it myself, having “great ideas” but never putting them to the test because they are too large for me to know where to start.

  • Juliet

    This is such a profound post, and I can completely understand where you’re coming from! I enjoy seeing the world around us as a holistic system, and that sometimes can lead to certain levels of frustration and the feeling that things are not changing for the better fast enough. I definitely agree it’s about finding the balance between having “big thoughts” and taking everyday actions towards them. I spent a lot of time reading about emergence, which really helped me to recognise the importance of small actions and their “ripple effect” that move us towards greater impact. Nature never fails to teach us valuable lessons! :)
    I also feel this balance in mind-set is much more healthy and sustainable both for ourselves and for our ecosystem. I admire how you and Buffer have always remained quite grounded despite of Buffer’s success and the external voices that might have tempted you and the team to be otherwise. :)
    Thank you for sharing these thoughts on the open blog! :)

  • Bryan Milne

    Hey Joel, some good food for thought thanks. Personally I think that while thinking big is not a bad thing and can open one to the possibilities I have also found that it can be daunting as it puts light on the gap between the now and the possible future. I prefer to see the end as one of many possibilities with interim goals (base camps) in-between that are more clearly defined the closer that they are to the current point in time. Thanks for sharing. P.S The “Called Student” link redirects to a FaceBook timeline

  • Ben Keene

    100% Joel. Thinking big and expectation of success often clash. I love thinking big, but try and always focus on the small steps. I use this to try and drive all my thinking and action: “Keep your head in the clouds and your feet on the ground.”

  • Ben Stevens

    Great post Joel! I do love the saying ‘Shoot for the stars and if you come up short you might hit the moon’ but this strategy represents a very grounded approach to getting to where you want to be in business. It also reminds me of another great approach proposed by Dave Lavinsky who talks about how companies can grow bigger and faster by reversing their business plan. His approach is based around entrepreneurs defining the clear goals they want to achieve and then working their way backwards in a step by step process until they arrive back to their present point in time – hence giving them a clear guide/map of how to get to their desired goal. Both very interesting approaches indeed. Thanks for sharing.

  • There’s something to be said for the journey you can take users on also. They both learn the product more easily at the start but also evolve with it as its features improve and grow.

    If you can develop new features just as users start to become aware of their need for them you can continue to wow them. Surprisingly I’ve only experienced that with a few apps… Buffer having been one of them.

  • Sylvia

    I’ve never considered that “thinking big” could have its downfall except possibly feeling unfulfilled or frustrated if you don’t attain those lofty goals…but after reading this article, Joel, I can see how it may take away from focusing on “the next step” or doing the “smaller” basic things well. Thanks so much!

  • Alvin V. Mapas

    Yeah… I love to do this, and I would definitely agree with the article. I always like to think big but it always ends there, and when its time to work on those big dreams, my work ends up in mediocre quality, honestly because of my laziness. I know I’ve got to change this cycle.

  • Salem Hephzibah

    Love this Joel. I was just thinking about this conundrum that big thinkers face. It can be our greatest strength and biggest weakness. Thanks for sharing, I can relate.

  • François Chabé-Ferret

    Dear Joel,

    First of all, I’d like to thank you so much for your inspiring work and for sharing such interesting thoughts ! I’ve been reading your posts for a while, and I must say it’s always a source of good thinking that helps me moving forward.

    Today, I’ve decided to write to you about this very post. As usual, I’ve started the reading with enthusiasm and curiosity, as the title really made me think of myself stuck between procrastination and a strong will to « make a little difference in this world » !

    Once again, I was delighted by the description of your problems and the questions you felt the need to answer. And I totally agreed with your first 3 points : how good and motivating it is to often « think big », how every single startup started small (usually : someone with a dream !) and how it is fundamental to be able to focus on small but essential concrete actions to finally achieve part or all of the « big thought » we first had.

    Now, I need to tell you that I disagree with two main ideas you shared in the rest of this post. And I’d like to explain you why (and I’d love to hear your thoughts about it !).

    Here are these two ideas (as I understood them) :

    1/ It is good and healthy for everyone to have ambitious thoughts, to « think big »… but not to much ! Otherwise, you venture to spend too much time thinking (not to say dreaming) instead of doing all the little things that will allow you to finally reach your actual goals.

    2/ You need to fight these world-changing thoughts if you don’t want them to stop you moving forward.

    First, « those of us who think big too much need to pay attention to this : a certain amount is definitely healthy, but beyond a point it becomes a huge time sink, and could actually stop you reaching your goals », you say. Here is what I read between the lines : if you keep on dreaming, you won’t be able to fulfill your commitments, defined as the little everyday actions you are supposed to do to get one step further and finally reach your goal. To me, your post is not about « thinking big », it’s more about commitments and how you struggle to fulfill them while being who you are : a dreamer, a « world-changing thinker ».

    Then, it’s fun but « inevitably (…) comes the time to get working again (…). You’ve got to stop thinking about changing the world, and do the nitty-gritty to get one step further », you also say. Again, here is what I read between the lines : what’s fun (thinking big) and real work (immediate tasks) can’t get along, and there’s a time you have to choose between these two activities ; and when this time comes, don’t make any mistake and focus on real work. To me, your post is not about « thinking big », it’s more about the place of dreams and fun when it occurs you have an actual job and responsibilities.

    These stakes seem complex, and I totally understand the difficulty you face in finding satisfying solutions. But believe me : they’re not that complex if you keep in mind who you deeply are. Of course, I don’t know you personally but I can tell dreams and world-changing thoughts are really important to you. And I’m sure your ability to « think big » – and how much you enjoy it – are some of the keys that explain your personal success so far, and of course Buffer’s.

    Now, here’s what I’d like to tell you : when you decide, on your own, to stop thinking big to get your everyday job done and fulfill your commitments, you trade fun for obligation. You lock yourself in your own prison and you’re not yourself anymore. So my question is : why ?

    You are the only one who can answer this question, but let me share a hypothesis with you ! I think there’s a time in life when the fear of loosing or waisting all one has already achieved becomes stronger than one’s desire to keep changing the world and achieving bigger things. This is a time when we all insidiously become more and more « managers » (of our lives, of ours companies…) and less and less « leaders ». Our main concern becomes the preservation of what we’ve created, and not the process of creation itself. For a dreamer – or at least someone who is still dreaming and thinking big – it’s a sad sad moment. Because it appears you have to give up or fight or distrust what made you feel alive and proud so far.

    Eventually, there’s a time for each one of us when we want to rest a little, think smaller and enjoy some kind of comfort – for a while or for ever ! And it’s a good thing, because we deserve it. But I’m pretty sure this time hasn’t come for you yet. And what allows me to say that is a simple fact : you can’t help yourself keeping on thinking big ! There’s no better proof.

    In reality, I think what you’re concretely doing today – despite how much you love it and how much you love the people you work with – does not completely satisfy you anymore. And now you’re dreaming of something bigger than all you already achieved. In Mark Suster’s words, I would say : you are in Basecamp 2, but you didn’t realize it yet. And instead of enjoying the point of view, the perspective and the new opportunities in front of you, you feel guilty, turn around and struggle with yourself to forget about all this (or at least not think too much about it).

    What you’re facing is a divergence of trajectories : your own personal path and your company’s (and the people working for it). This divergence may also be a difference of speeds. Whatever it is in reality, I’m sure there are many other ways to figure out a solution than the sacrifice of your will to « think big » and change the world !

    This is one of the true injustices in creating and owning a startup/company : without your ability to dream big and your leadership, nothing would exist. But this whole process of creation doesn’t give you any particular skill or palatability for management. Yet, to exist, grow and thrive, any human project needs both leadership and management. For a natural leader (or dreamer : these are synonyms to me), it’s a full (and maybe long) learning. But for a natural manager, it’s probably a way longer path to learn dreaming big !

    To conclude, my conviction is that your « world-changing » thoughts are what is most precious for you and your company : you should never fight nor sacrifice them. A company whose leader has stopped dreaming always turns into a sad and anesthetized place. Management is one of the keys you’re looking for. And my first recommendation to you would be : most of your time consuming tasks symbolize Basecamp 1 for some of your teammates, so reassign them, help these chosen ones to learn and achieved their new missions… and, Joel, keep on climbing, dreaming and thinking big !

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