The 5 questions successful entrepreneurs ask about their past

What led you here has secrets. The place you are now is a culmination of your thoughts, words, and deeds thus far. If you are in a good place, the effect was generally positive. But even then, could you have done more? Could you be further? How do you know you’re in the best place to be?

The truth is you can’t know. But you can guess. Everyone has weaknesses, shortcomings and blind spots. How do you make sure those who hinder your present self don’t move on to your future?

Deep self-awareness is the answer, and it is obtained by asking the right questions. This isn’t about regretting or wanting to change history, it’s about continuous improvement in an effort to become the best. Here are five questions to think about and write about to make your future better than your past, no matter where you are now.

What led me here?

Narrative fallacy is where disconnected elements seem to make up a story when you look back. But here’s the story that matters. When did x lead to y? How did your personal story go? Which movements were responsible for your biggest breakthroughs, which decisions really touched the needle in your company? Who were the people who opened those doors and who are you grateful to have in your life?

An analysis of the factors contributing to your greatest successes and failures to date is worth gold. Seemingly random events can hold answers to the true cause and effect of your success. Your story so far won’t change, but what you take with you into the next chapter will. Make it intentional.

What stopped me?

What hindered your progress instead of what helped you move forward? Which opportunities have you narrowly missed and why? When did you think too small, ask the wrong person for advice or just play too safe? If you had the time again, what leap would you make? How would you have built on your foundations differently?

Something that held you back in the past has no place in your future. The doubting friend, the risk-averse accountant, the naysayers and haters and backhanded compliments may have cost you more than you realize. Find out what held you back from removing it from your future.

How could I have done better?

You used to be young and naive and in the future you are experienced and wise. Current you navigate the journey between the two. If you’re not ashamed of your past work, it’s a sign that you’re not making progress. So what about your past isn’t good enough for your future? Where do you know you can improve and where have you already started?

What situations were you not prepared for and how could you beat them next time? When did you feel like you hadn’t done your best, when did you shortchange yourself? Showing up unconditionally is required for your next step. Where we’re going, there’s no half-arsing it. Find out where you’ve given everything so far and promise nothing less than all-in in the future.

What can I learn?

The patterns of your past years contain secrets, lessons and understanding. Imagine your journey so far in the form of a history book. Imagine a third party looking at the facts and drawing their conclusions. What would they collect and how would they make their assessment? Immerse yourself in the events, go into the details. Note that the trends of your actions are converted into results.

Everything you’ve done so far has paid off. If you want to change the results, you must change the input. Getting to know the effect of the input comes by looking back and researching. Think about what you can learn in the coming years. Start again armed with all that knowledge.

What should I change?

There are elements of your life and work to date that should not be transferred. There are things you do every day that don’t serve you. Some people lift you up, others disappoint you, but unless you analyze you don’t know which ones. This thought experiment involves imagining the changes you could make and writing a list. Then project each list item forward. What would happen if you made the change?

If nothing changes, nothing changes. You keep going and your progression is linear. But what about the exponential growth you so desperately want to find? It is discovered through change. Changing your geography, changing your business, changing your habits, appearance or attitude. They’re all up for grabs as you transform into an enhanced version of yourself.

Journal on these five questions to build a healthy future. Dig into the past to ask what got you here, what held you back, how you could have done better, and use what you learn to influence what changes you. The old you brought you here, but the new you takes you there, prepare them for success in the best possible way.