Questions to Ask Yourself Before Starting

The biggest tragedy for any founder isn't failure. It's becoming trapped inside a business that you don't actually like.

If you could build any type of business you want, why would you build one that makes you miserable?

Ideally you wouldn't, but it happens surprisingly often. I've interviewed 500 successful founders, and many of them can't wait to quit so they can start over and "do it right this time."

It doesn't have to be this way.

What do you want for your life?

We all want different things. Many of us want to be rich. Some want fame. Others want more time, creative freedom, or the ability to work from anywhere on any schedule. It's not hard to see how a business could provide these things.

But what about more exotic desires — can a business help with those?

What if you want to hang out with your favorite celebrities? Or travel and be guaranteed to meet new friends all over the world? Or regularly eat at all the best restaurants? Or have tons of people read your writing and ideas? Or befriend successful and inspiring people from a particular field? Or get fit and stay that way?

I know people whose businesses have enabled them to do all of these things. In fact, I'm a prime example — I literally have to talk to interesting people every week, because I started an interview-based podcast.

No matter what you want in life, starting a business is a powerful way to help you get it. But you have to know what you want first.

Getting to Know Yourself

The easiest way to figure out what you want your business to do for you is to start asking and answering questions about yourself.

This should be your first step as a founder. Before you come up with an idea, before you find a partner, before you do anything, take the time to examine who you are.

I've typed up a list of questions below. You don't need to use this exact list. It's just here to give you a rough idea of what I'm talking about:

  • What kinds of things have I enjoyed working on in the past?
  • What kinds of work have driven me insane in the past?
  • What am I passionate about?
  • When was the last time I was so excited I could barely contain myself?
  • What about the last time I got really angry about something?
  • Am I usually happier working alone or with other people?
  • How much free time do I want to have in my life?
  • What do I absolutely love telling other people about?
  • What have I spent the most time in life learning about?
  • What do I believe that most people don't?
  • How much money do I want to make?
  • What kinds of people would I like to meet and interact with?
  • What am I particularly good at?
  • What am I bad at?
  • What kinds of praise and accolades have I gotten in the past?
  • What is it that people say about me that makes me feel the best?
  • When am I good at motivating myself, and when do I need others to hold me accountable?
  • What do I never get bored of doing, even when it gets hard?
  • What gives me energy?
  • What stresses me out?
  • What kinds of errors and mistakes have I tended to make in the past?
  • What do I want to learn about or get better at?
  • Who do I respect?
  • Whose life am I jealous of?
  • What do I wish I was forced to do on a regular basis?
  • What kinds of people, if any, would I want working alongside me? Any specific individuals?
  • What aspects of my life do I want to keep intact no matter what?
  • In an ideal world, what kind of life would I want to live, and what kind of person would I be?
  • What would I like to change about the world around me?
  • What parts of running a business scare or worry me? What parts excite me?

Sure, it's a lot of questions. But any business you start might last for years or even a lifetime, so it's crazy not to spend an hour or two upfront thinking about the kind of person you've proven to be.

And be honest! Don't self-sabotage by lying to yourself about any of these questions. Later on when you're coming up with a business idea, you'll be much better equipped to evaluate whether it will make you happy (and tweak it accordingly) if you have accurate answers to these questions.

A Working Example

Before I started Indie Hackers, I knew I wanted something…

  • that I could create quickly (because I was running out of my savings),
  • that was simple to explain to my friends and family members (because I'd be lonely if I couldn't talk about it),
  • that would encourage me to meet fascinating people (because I'm a big believer in surrounding yourself with your role models),
  • and that wouldn't require too much coding (since my biggest weakness historically had been spending too much time coding).

Having a list like this made it easy for me to throw away some of the other ideas I was considering and focus on what seems to have been the right one.

In fact, having this list helped me come up with the right idea in the first place. We often worry that constraints will limit our choices, but more often than not they simply serve as prompts to boost our creativity.

Your business can help you accomplish anything you want in life, so remember to aim high. But more importantly, just taking the time to aim at all can work wonders.

  1. 32

    I think it's easier said than done. And you can ask all these questions, but reality, life and change happens.

    I've succeeded at a business that I do love, but I don't necessarily want (anymore). Is that different from a business I don't like?

    I would often ask myself these types of questions. Sometimes I think I'd want things, then something happens (life, eh?) that changes my mind. Or the world changes dramatically within 5 years and all of a sudden what I thought I wanted is definitely not I want now. The person I am now is most definitely not the person I was 5 or 10 years ago. And most definitely nowhere near who I was 12 years ago when I lay the seeds of what I was doing.

    I think in my case, the business grew out of the things that I loved doing but it has outgrown me.

    It has morphed into something that I believe is the best for the business to be sustained, but not necessarily the best for what I want out of life. And for me, I'm ok with that (kinda, for now), but it doesn't make it easy. I no longer want the responsibility, but it feels wrong to shape it into what I want.

    And yes, I know businesses can be sold, but people like to think that that is an easy process.

    1. 4

      Yep, it's only natural to grow and change as a person over time. Very few of us want the same things forever. And sometimes as founders we're faced with a choice of continuing to do what we love vs letting our babies outgrow us because it's right for the business. But unlike real babies, we don't have to feel too bad about selling them or handing them over to other people to run ;-)

      In your case, I'm selfishly pretty happy that things changed and you eventually moved on to help run Indie Hackers!

      1. 6

        One thing that sticks in my mind is that people often have views that they express and feel strong about and sometimes other people take them too seriously, or become blinded by them.

        I feel it's important to have a broad view of the options and feel that whatever option you take at that point in your life is the right one at the right time, even if it doesn't quite go to plan.

  2. 15

    Good post but I'd add a disclaimer, only ask those question if you already started ventures before. If you haven't just start AND finish something. Even the worst idea you have. Otherwise you will asking yourself questions forever, loosing time and will never work on anything.

    Yes, working on the wrong idea might be bad but not working on any idea while just reading and asking questions is worse.

    1. 18

      If you're someone who spends forever reading advice and never starting, the best advice is always stop reading and start. 👍

    2. 1

      One of my mottos in life is: "Just do f* something".

      So may of my people have all these idea, but that is just it, Ideas

      Also, when I build something, these same people have so many criticism.
      But ....

      1. Its much easier to criticise
      2. Build something yourself then we talk again.
  3. 5

    "You’re building your first house for your enemy, your second one for your friend and your third one for yourself"

    The same applies for startups I think.

  4. 4

    In my case, I realised I was stuck in this advice loop of launch fast, speak to people, validate, validate, take your developer hat off, etc. On all the projects I was working on I was ending up burnt from all these processes that apparently I was not enjoying that much.
    Yes, I would like to have a product of my own with a healthy business model, but you should filter the advice you get from other founders through your lifestyle and character filter.

    I like to build stuff, period. I have a 100% remote part-time job that brings cash in, so I'm just gonna enjoy the building process and I'll know that eventually, I will make money out of it. Until then, I'm going to enjoy life, travel and build software. 👨‍💻

  5. 4

    I may be an outlier, but if I'd started with all those questions, I still wouldn't have chosen anything! Instead, I'd have spent years examining potential businesses (and myself) against that list and at most have written a book (or series) in my journals that nobody else would ever read.

    At least for me, a tighter loop between analysis and actually doing things is much better than a massive list to run every business idea against.

    1. 4

      Right, I don't think one needs to be overly systematic about it, or expect to get a perfect score, or anything that limiting. A bias toward action is important for a founder, which means avoiding analysis paralysis.

      For those who struggle with getting started, I suppose all the advice on the Internet is moot and should instead say, "Just start something already!"

      But for the remaining pool of founders who start things but struggle to succeed, I think they generally could afford to be more thoughtful.

      Success is the product of both high-quality decisions and actions, not just one or the other. And it's an exercise for the reader to figure out which area they need the most help with, if either.

      1. 2

        You know what might be really useful (but also more work)? It would be we if could see you or others with similar workflows go through this process! That would fill in a lot of the inevitable assumptions / differences between how we imagine this process vs what's in your mind while writing it out.

        The way I approach each of those bullet points is at least a couple of pages of journaling, then quite a bit of time going through the responses that are contradictory or mutually exclusive or dependent upon each other. Clearly your way of going through such lists of broad, personal questions doesn't lead to fractal rabbit holes, like mine does, but it's not easy to imagine what the process is like.

        Also, do you have a 80/20 version or your list?

  6. 3

    Love this. Reminds me of the What, Why, and How questions.

    However, still have something that bothers me. I've come to realize that the hard things I run away from are sometimes the things I need to sort out. Been trying out different ways to go about it. For instance, I'm learning a bit of front end design but I have been running away (with so much vigor) from anything business mgt related.

    Dunno but I think it's important for me to have experience in this. Any suggestions?

    1. 1

      I do the same. I think most people do. I explicitly remind myself on a regular basis to check and see if there are any scary-but-important things that I'm avoiding out of pure fear, laziness, or competence. Often the answer is yes, and that's fine. The most important thing is to diagnose it when it's happening and correct for it.

  7. 2

    Really nicely written Courtland. Thank you.

    I think one thing that's been uber valuable for me is this deep balanced understanding:

    on one hand

    to aim high, since I have a lot of control on defining where I want to go, what I want to experience and what outcomes would rock my boats.

    on the other hand

    to welcome all the amazing possibilities, since there are a lot of surprises, coincidences and opportunities that show up, which are not even in my field of view, much less control, yet that make the whole journey, not just the destination, rich.

    Hope you have an awesome day! ✌️

  8. 2

    Great article. But I didnt find anywhere where it talks about solving a problem that people are having. Y Combinator teaches that you first start by identifying a problem and then go ahead to provide a solution.
    This article seems to be about passion and what you like. You may have passion for something but people won't want it and thus nobody pays for it. And you might identity a problem that might not be your passion.

    So which is it? A problem or a passion?

    1. 1

      Problem that aligns with your passion. I like to write and I do that a lot. I spend time on writing communities, platforms and forums. That way I know more about the problems that I have interest in.

  9. 2

    I needed this :). Thank you, hopefully, I will launch something here soon :) and something I love!. I think being honest and answering those questions kind of narrows down things as you said.

  10. 2

    Getting to know yourself is a huge aspect that I didn't really think of for thegoodstartup.com's audience until reading this! Finding what you care about is such a crucial step in finding how you can make the biggest impact on the planet...will be thinking about this more!

  11. 2

    Inspiring, thanks Allen!

  12. 2

    Although one might ask himself all these questions, sometimes circumstances take you to embark on a business that maybe doesn't align with all of your answers. Ideally, we'd be able to start a business that aligns with all of them and that's the objetive. There's the 'happy path' and then there's all the other paths. The most important thing here is to be honest with yourself and what you're aiming for.

    Would be interesting to have this kind of content in a more discussion-like format on a podcast maybe? Wait a minute... YOU don't have your own episode on the podcast, do you @csallen?

  13. 1

    If you're someone who spends forever reading advice and never starting, the best advice is always stop reading and start. 👍


  14. 1

    really helpful questions courtland ❤️

  15. 1

    I found indie hackers from Ali Abdaal YouTube channel which I must say at the right time because I was contemplating saying "fuck it" and start one of the ideas I have for a business.

    This website and this particular article is a right step in the right direction. Thank you.

  16. 1

    The problem is not creating something after you have discovered yourself, the problem is getting people to use that something.

  17. 1

    Excellent article, Courtland. Thanks for questions. 🙌🙂

  18. 1

    Hi Courtland - is it bad or good that a majority of my answers are all the same? i.e. bad that I am not thinking wide enough or good - as that is my passion that I want to drive to my vocation. Cheers Hulkster

  19. 1

    Great exercise. I still would have started by last business after doing this exercise, I just would have probably kept is smaller for longer to enjoy it more.

  20. 1

    This is encouraging. Bookmarked for more reading and thinking.

  21. 1

    @csallen I'm curious, was Indie Hackers your first attempt after this exercise?

    1. 1

      Yep, I'd never gone through an exercise like this before starting any of my previous businesses. I just started working on whatever idea seemed to be a good opportunity at the time.

  22. 1

    Courtland, it was a bit of a shock how many times I wrote down certain things during this exercise. I've identified themes and things I care about more than I even thought I did. I have a good feeling about the road to come. Best, Taylor.

  23. 1

    Courtland, Very interesting to reflect on these questions. As an older community member, the reality often is that when push comes to shove, if you want the business to be successful it may have started with the foundation of good intentions, but the customer's desires often pull you or push you into a new direction. Few of us have the strength to tell a potential revenue stream "no" when the fumes in the wallet are wafting away. I've been in businesses that were purely focused on the customer and the first order of business was keeping the paying customers happy while employee/owner satisfaction wasn't a KPI. So I'm not shocked that you have found a good number of the 500 entrepreneurs as being less than excited about waking up every day.

  24. 1

    Thank you for this , I hope it will help me get a way all the confusion that I have .

  25. 1

    its really amazing to read such text .There are a lot of powerfull and inspiring human beings on earth and you are one of them.I wish i learned about indiehackers as it lauchen but i will just get the best out of it now and develop myself and all people around me.
    i want to thank you personally for shring this with us and big thanks to all those behind Indiehackers.
    I am a Student in Germany, working partime , passionate about (actually more than passionate its my everything) Dance and music , Technology and Computer science , Phylosophy and the Human Being.
    I like quite all the areas of IT , but i will like to be active in Cyber Security and Software development .

    if any of you can advice me or exchange some text with me from time to time i will be grateful

    Thanks again

  26. 1

    Good post - just thought I'd mention a small typo here: "before do anything" -> "before you do anything"?

  27. 1

    A very wise man once shared with me some advice:
    "That is a problem I would like to have"

    If I have business I don't like, then I will fix it. Getting to that point is really difficult, and I wouldn't for one moment decide not to build that company.

    "It is better to have loved and lost, then never to have loved at all."

    1. 3

      A very unwise man once said...

      "sounds good, doesn't work"

      In this case though, I think he was right.

      You can't always adapt how your business works, which customers you have contact with etc to fit in with your lifestyle goals later.

      Eventually, something will give. And your health, personal relationships or business will suffer because of it. It isn't worth wasting (and suffering for) years of your life.

      My favourite example of this is how @bentossell iterated through lucrative versions of 'no-code products' until he found a business (model) he actually wanted to work on and that fit his lifestyle goals.

      1. 3

        You can't always adapt how your business works, which customers you have contact with etc to fit in with your lifestyle goals later.

        Strong agree here.

        It's easy to say, "I'll just fix my company," but the more time that passes, the harder it is to make changes. Eventually you'll have lots more code, customers, revenue, employees, etc. all acting as momentum pushing in a particular direction.

        The easiest time to make changes is at the start. As the saying goes, an ounce of prevention is worth a pound of cure.

        1. 1

          While that is true, changes at the start are also the most costly investments. So you need to constantly do analysis to determine, "If we do A instead of B, will we be able to reverse the decision later with an overall net gain." Usually doing B instead of A now results in a failed company.

          Everyone should focus on their non-negotiables, but that doesn't mean you get to create every aspect of a company you are happy with. Fix the most important problem first.

      2. 1

        @louisswiss can you link to an interview or post where @bentossell talks about that strategy? Thanks!

    2. 1

      It's actually not as hard as one might think to start a successful business. You can make mid-five figures panhandling on the street in most cities if you're strategic about it. Of course none of us want that business—it would certainly score pretty badly against the list of questions above—and so we don't start it.

      From there upwards, it's just a spectrum. You have to find the minimum cutoff point for your happiness. Or do you?

      I'm not so sure you have to compromise. Many of us have a scarcity mindset around ideas. We think that viable business ideas are so rare that it's worth working on things we hate just because they have a shot at working. I think this is a misconception, and that viable business ideas are actually quite straightforward to come up with, so there is no need to make that kind of tradeoff. But that's a topic for another post…

      EDIT: Here's the post!

      1. 1

        Where I'm struggling right now is to come up with a viable business idea that fits my experience, skills, and interests. It seems like most successful businesses are a natural outgrowth of what their founders 1) are good at, 2) are knowledgeable about, and 3) care about. I'm having trouble figuring out something that covers those three bases, that would also provide value to other people.

        1. 2

          It helps to prioritize the most challenging and important constraints and deprioritize the rest.

          For example, I wouldn't worry too much about skills and knowledge. You can do some combination of learning on the job and faking it until you make it there.

          However, you don't have much control over the markets and the problems people find valuable enough to pay for. So that might be a good place to start.

          It's hard to give you more specific advice, since I'm not sure what your skillset is, what you care about, etc. But I think @GNaylor nailed it when he said that viable business ideas are more straightforward to come up with than you might think.

          One reason that's true is that the vast majority of successful business ideas are businesses that have already been done. There is a staggering number of profitable restaurants. There are dozens of analytics tools. There are countless people starting businesses to help people learn to code, or to pass coding interviews, or to help companies hire developers. Etc etc.

          Also, imo people don't put enough deliberate effort into coming up with business ideas. For example, the idea for Indie Hackers was the culmination of three full days of research and brainstorming. I probably read through thousands of stories and ideas and came up with hundreds of my own in that time. But I look around at others, and they're just sitting down waiting for inspiration to strike. That's incredibly unlikely.

          1. 1

            Also, imo people don't put enough deliberate effort into coming up with business ideas.

            removes glasses

        2. 1

          I think that particular block you describe is more common than we sometimes think (and I would identify with). What csallen and others heavily hint at is that viable business ideas (and therefore businesses) are more straightfoward to come up with than we give credit.

          Summarised, are we overcomplicating the process?

          If it helps, I'm more than happy to DM and go through some ideas and give feedback (from one 'stuck' person to another). Who knows, maybe we can both identify a way forward!

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