The Questions That Scare the Shit Out of Me, But I Don’t Tell Anyone

It’s therapy time. In no particular order, the following is what follows me around every day and I never say to anyone …

• I’m not getting any younger. Will I look back 10 years from now, and regret what I’m doing today?

• Have I missed my window on success?

• Will I ever get to see my vision followed through completely?

• Am I good enough at what I do? Everyone seems smarter than me.

• Will my product work like I hope it will?

• Will I be broke forever?

• Will I ever be able to raise money again?

• Will I always be jealous of other people’s ideas, businesses and successes?

• Will I have to work for someone else?

• Can people tell that I’m full of shit at times?

• If investors are investing in me, when they say “no”, does that mean I’m not good enough?

• Are others working harder than me?

• Am I even doing the right things?

• Does any of this even matter?

• Will I ever satisfy my hunger, or is it just an endless road?

• Do I have what it takes, whatever that is?

• Will I ever lose the chance to be an entrepreneur?

Does anyone else feel this way?


  • Completely. These questions I ask every day. I wake up in a cold sweat. But asking the questions is the answer. It means we are not zombies addicted to paychecks.

  • My favorite one was:

    “Can people tell that I’m full of shit at times?”

    Yes I wonder this every day. As a founder sometimes you have to be full of shit for the betterment of your team and I often wonder if people can see right through me.

    Thanks for sharing.

  • • Have I missed my window on success?

    First you need to define what success looks like to you. Is it money, fame, making a decent living and do what you love? If you are thinking of doing the 100m in under 8 seconds you have little chance, but much more likely to exit with some money in your pocket.

    • Will I ever get to see my vision followed through completely?

    A bit of luck… Timing / Execution / Team / Runway will help define this one.

    • Am I good enough at what I do? Everyone seems smarter than me.

    You got this far… Most people just talk, whilst you are walking the walk! Also, everyone you employ should be smarter than you, that is a good trait to have in building a winning team that can execute against the odds.

    • Will my product work like I hope it will?

    This is a hard one, you need to test and get a highy optimised feedback loop going. In some cases, the users will take over and you need to work off data to determine where it comes.

    • Will I be broke forever?

    Most founders will stay broke in the early years but understand the risk / reward. It is knowing and having the confidence when to pursue and when to give up when things are not working.This is difficult one most struggle with.

    • Will I ever be able to raise money again?

    This is going to be based on your previous performance and the value for new/current investors. Fund raising is hard period, but not impossible. Keep with it…

    • Will I always be jealous of other people’s ideas, businesses and successes?

    This will suck the life out of you. You need to nip this in the bud straight away… It’s hard enough to spin plates but don’t let this one bring you down. Put all that negative energy in your product. Build something great.

    • Will I have to work for someone else?

    Possibly; but that is the risk everyone faces. Also, you are always working for someone else. Your customers and/or your investors pull the chain, rather than you being a direct employee.

    • Can people tell that I’m full of shit at times?

    It’s one thing to keep the team up and another to plain bullshit. The latter can catch you up and trip you over. If you can find a way of not answering certain questions, then do that. Even if it’s harsh. People rely on you and if you disappoint them it spreads as fast as being honest. There is an old saying “A reputation takes years to build and seconds to lose”

    • If investors are investing in me, when they say “no”, does that mean I’m not good enough?

    Nope. You might not fit their remit (knowledge in your industry/ add enough value / wrong vertical).

    • Are others working harder than me?

    People work hard all there life and end up with nothing. You know deep down how productive you are. A good start is to get up early everyday, eat well, break a bit of sweat (20 min run) and sleep 8 hours. Do all the most relevant stuff that makes a difference for at least 8 hours a day. Email and having long meetings are not going to get shit done. Focus hard on what matters and you will out work the 16 hour a day guy that did nothing meaningful and burnt themselves out in 12-18 months.

    • Am I even doing the right things?

    Look at your cash-flow, this is a great tool to get your priorities in order…

    • Does any of this even matter?

    Everything matters, but order them by what matters most and dump the stuff off where possible.

    • Will I ever satisfy my hunger, or is it just an endless road?

    Take a piece of paper, write down everything you want. Then systematically determine weather you really want it, how you are gonna get it and put a timeline next to it to achieve it. You may find you dump half and double down on the other. Making you success rate higher.

    • Do I have what it takes, whatever that is?

    Ask yourself that later and focus on the here and now… You are still here, so by default you have what it takes.

    • Will I ever lose the chance to be an entrepreneur?

    That’s the same risk we all have everyday. That little sick feeling you get at the bottom of your tummy. That right there is the signal that keeps you in the game. When it gets to much, that’s the time to stop being an entrepreneur. Unless you are Elon Musk, apparently he had no fear jean in his body.

    *Does anyone else feel this way?

    Just about everyone, you are in safe hands here…

    Hope this helps

  • Yep tis the problem, you are over thinking everything. Drink wine. Throw a good drunk at least once a month. I recommend a good Kentucky Bourbon like Woodford Reserve. The people who make shit happen are making it happen not sitting around thinking about life. Life will work itself out. 🙂

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