How do I stop “analyzing” and pick between two good choices?

This is part of an ongoing startup advice series where I answer (anonymized!) questions from readers, like a written version of Smart Bear Live. To get your question answered, email me at asmartbear -at- shortmail -dot- com.

Embarras de Choix writes:

I have a startup with thirty paying customers. We’ve been bootstrapping up to this point.

I think there’s a big opportunity to raise money, but also I could continue as I have been. I don’t know way to go.

I already know the pros and cons of the decision, so don’t lecture me about that. I just don’t know how to pick!

This is one of those few dilemmas where there’s no wrong answer. So, whichever you choose, never let anyone else make you feel guilty about not choosing the other.

But “there’s no wrong answer” doesn’t answer the question.

Asking for more advice from other people probably won’t resolve it. While I was bootstrapping WP Engine I constantly heard that we’re hamstrung by not taking an investment; after raising a Series A a different set of people expressed their disappointment that I had “sold out.”

Who’s right? Both. Neither. This is why you cannot look externally for the answer.

Every day you delay the decision is costing you. Dithering doesn’t move you closer to either goal — it’s draining time and energy from whatever is actually valuable, and it’s blocking other decisions about spending money, hiring, your lifestyle, stories for the press, features, everything.

So you need a fast decision, and other people cannot give you the answer. That leaves you, alone.

What kind of company sounds like the most fun to build?

Do you like working alone or with a very small team? Does hiring ten people in the next 12 months sound exhilarating or depressing? Do you like having a hand in everything or would you rather be evangelizing and leading? Do you enjoy carefully, slowly growing a backyard garden or would you have more fun strapping on an afterburner and seeing just how much of an impact you can have on the Earth? Do you like being good at what you’re good at now or do you want to learn how to run a completely different kind of business?

Are you proud of bootstrapping? Do you enjoy the balance in the conversation when you tell that to someone funded, tacitly saying “I’m in control, I don’t need help, I have a product so good people actually pay for it?” Or does it make you feel small, knowing you’re not growing as fast as you could, not making as much reach as you could, not making as much money as you could?

What sounds like fun? Yes, fun. Enjoyable. Fulfilling. This is your yardstick.

I think fulfillment and joy barely enter into the calculus for most founders, and that’s a mistake. Why build a company — or anything else for that matter — if it’s not fulfilling?

You’re in an enviable and rare condition in that both of your options are valid and rational in every way, and that means you get to pick based something we all really ought be valuing, but lack either the means or courage to do so.

But you can.

And remember, five years from now when you look back on this with hindsight, you still won’t know which one would have been “right.” Even if the path you picked “failed” in some objective sense, you still won’t know that the other necessarily would have been “better” — more money, more fulfilling, happier, whatever.

P.S. Other people can help, in that they can help ask you more questions. But only you can decide the answer.


Add your advice to the discussion section!

18 responses to “How do I stop “analyzing” and pick between two good choices?”

  1. Awesome analysis Jason! I love your point that you should be looking internally for the answer, not externally. I know my personality tends to compile as much info as I can to make “the right decision.”

    But as you pointed out, there’s no wrong decision – so I need to make the right decision for ME! 

    Thanks for the reminder! Always timely in our info-overload world.

  2. Don’t remember where I read this, but was told to flip a coin.  Not because you’ll take the coin’s answer, but because while it’s in the air you’ll start hoping it comes up the way you really want it to.  That’s your answer.

    • Great comment Philip.

      I was going to say exactly the same thing – and I have used it on countless occasions – generally with other people who are dithering on a decision. It works. It cuts through the over-analysis. 

    • I never looked at a coin flip that way. You brought up a really good point, Philip. Some people say that they can’t decide on picking between two things, but there’s something that I read before that says that by saying you can’t decide, you have already made a decision that neither of those are your answers.

      = Gerald Martin =

    • Yeah but what if you start having doubts ?
      The most I can say….Sleep on it ,maybe try both see what you like the most

  3. Great article. I always say you should go with your gut (and Philip’s idea of flipping a coin is a great way to trigger that), which is way better at distilling all the myriad analytical factors down to an outcome. My take on this is here:

  4. Maybe one important point missing here is who you would raise money from?  If you can’t decide right now, perhaps it’s because you haven’t found, or you’re not sure you can find, the right investor. 

    I’m curious, is it realistic to try to expand your network and talk to potential investors, while still concentrating on growing your business?

    • Sure it’s realistic, you just set expectations.  You can reach out and say “I’m doing this, I’m not ready to raise money yet, but you’re someone I might want to talk to.  Is it OK if I give you short monthly updates on my progress?”  Then you can develop a history and rapport.  Then when you’re really ready you’re not a stranger in the office, you have something to base it on.  You’ve proved you execute what you say you will and that you make steady progress — two things investors are banking on and is otherwise hard to know.

  5. This suggestion might seem to too analytical for some but it is not the numeric outcome that is as important but the structured process that can help you decide what is most important on a relative scale and then make the call.  I agree with the internal focus. Pros/Cons is a great start to help identify relevant factors but Pros/Cons is not as helpful for complex decisions and it does not include the importance of the factors.  

    A different approach is to set up a simple table and follow these steps:1) For the decision, list the factors that are important (do a brain dump)2) Go through and add importance to each factor on a scale of 1 – 5, with 5 being very important.3) For each option, rank each factor listed in #1 for that option using the scale of -3 for very bad up to 3 for very good.  4) For each option multiple the importance of the factor times its rank, them sum all of the results for that option.5) Compare the sums and choose the one that has the highest score.Again, what is really valuable with this approach is not just the numeric output but the process of trying to identify relevant factors, determining how important the factor are, and then thinking through each option.  This is overkill for simple decision or decisions that are easily reversible. I have found that when the scores do not seem to mesh with my gut (similar to coin toss suggested below) that I need to reassess and when I do I usually learn something important about the decision, my implicit assumptions, etc.  This approach often works for  choosing between more than 2 options as most decisions are rartely binary (even if they seem so at first).  Hope this helps and thanks for a GREAT blog Jason!   

    • That’s a good process — it causes you to reevaluate your assumptions and forces you to think about implications.  There’s no rule that you have to pick the “first thing” in the end — the process is the value.

  6. The advice about flipping a coin to see if you like the answer reminds me of the advice a professor I once had.  He said that most of the time human beings don’t really make decisions based on logical analysis; we use the logical analysis to justify the gut decision we’ve already made — so the trick is to figure out what that gut decision is without all the bother, and then to be comfortable with it.

    He put this a bit more succintly for us: Imagine someone’s standing there with a gun to your head and telling you that you have to make a decision right now one way or the other or they will shoot.  You’ve got two seconds; which way do you jump?  That’s nearly always the way that you’ll decide after weeks of agonizing over it, too.

    And then he did this as a class exercise, with a pointed finger as an imaginary gun, and questions that we’d each written down earlier as ones that we were struggling with.  It was rather memorable.

  7. The harder it is to decide, the lower the difference in values between the choices. Ultimately, you either don’t have sufficient information and so you can’t really tell which one is better, or you’re being lazy and one of the choices is ‘harder’ or otherwise less appealing. (That choice is generally the correct choice, especially in a close contest — you’re negotiating with yourself and losing.)

    • more concisely: if you’re really having a tough choice and one is not markedly more difficult than the other, then which one you choose doesn’t matter as much as you might think, existentially.

      Even more concisely: Schrodinger.

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