3 Questions You Don't Ask Yourself Enough

Let’s face it: You probably don’t take enough time to reflect on your wild and crazy startup life.

It’s understandable though. Between work, relationships, and other responsibilities, there are some days where there is barely enough energy to wake up in the morning.

But what if there was a better way?

What if instead of putting your nose to the ground and speeding forward at 500 mph, you looked up from time to time to see if you are even headed in the right direction?

Reflection is by far the best way to stay on track with your goals and be successful as a startup founder. If you can carve out time each day, week, and each month to ask yourself the following questions, I can promise you will reap massive rewards:

1. Is This The Best I Can Do?

Think about your day for a second. Not just the time you spend on your startup (even though that’s probably 25 out of 24 hours at this point). Think about your entire day, from when you wake up until you fall asleep.

How often do you reflect on what you’re doing and critically assess your performance?

It’s very easy to get caught up in the day-to-day grind. Once we figure out what we deem “good enough,” it’s rare that we actually take the time to assess if we want to do better than just good enough.

Here are some questions to ponder:

  • What does my morning routine look like? Do you even have a routine, or are you just rushing out of bed? Are you inspired to tackle the day, or are you cursing the sleep gods for forsaking you yet again?

  • How am I spending my down time? When you’re stuck in traffic, do you listen to educational material or do you just blast music? When you head home after work, are you watching Netflix or reflecting on your day?

  • Am I taking care of myself? How often do you take time to workout? What foods are you putting in your body? Are you getting enough sleep? Do I meditate?

  • What assumptions am I making about my business? Is there any process in place that can be improved? Are you maximizing productivity, or just wasting time in meetings? Are your employees truly happy to work there, or are they just there for a paycheck?

These questions are just the tip of the iceberg. The point is to get you to realize that there are a lot of parts of your day where you are simply stuck on autopilot.

Once you realize autopilot is not always the best you can do, that leads to the second question…

2. How can I do better?

Ok, first pat yourself on the back for admitting you have a problem to begin with (AA would be proud). Now here comes the hard part: you actually have to put in the work to turn a problem into a solution.

So if you’re stuck trying to figure out how to do better in an area you know needs improvement, motivational speaker Jim Rohn laid out the following 3-step process:

  • First, figure out what you can do. Based on your current skill set, what steps can you take right now to solve the problem? Let’s take your morning routine for example. Experiment with going to bed earlier, waking up earlier, “eating the frog,” or any other change that will help you feel more inspired and productive after you wake up.

  • Second, figure out what you can read. Before you dive headfirst into reading material, understand that learning is a skill as well. So I highly suggest you read this article by Farnham Street and listen to this podcast episode by Tim Ferriss (and take copious notes). Then you’ll be ready to explore the magical world of google and amazon to find insights you can use to improve your life.

  • Finally, figure out who you can talk to. A key strategy to accelerate your learning curve is asking questions of experts. These people have already experienced what you’re going through, and can provide the wisdom you need to excel. Once you convey to them that you have already taken action (step 1) and improved your knowledge through reading (step 2), experts will be that much more receptive to helping you out.

Great, so now you have figured out what needs to be improved, and also figured out how to improve it. Don’t forget to ask yourself this last question…

3. Is it ok to fail?

We don’t embrace failure enough in our society. It’s a tragedy, and I beg of you please do not beat yourself up if your first attempts at making a change for the better fail.

In fact, take this quote from Atul Gawande to heart: Competence is knowing you will make mistakes and setting up a context that will help reduce the possibility of error but also help deal with the aftermath of error.

In other words, you will not become competent at anything until you accept that you will make mistakes. It’s a natural part of learning.

The goal is to learn from your mistakes and keep iterating until your new skill becomes second nature.

So just remember that every failure moves you one step closer to mastery.


In conclusion, reflection is critical for success and your overall happiness. If you schedule time to reflect, and honestly answer the three questions above, you will be well on your way to achieving both.