The 5 Questions Successful Entrepreneurs Ask About Their Past

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

The truth is, you can’t know. But you can suspect. Everyone has weaknesses, shortcomings and blind spots. How do you ensure that those hindering your current self won’t carry forward into your future?

Deep self-awareness is the answer, and it’s gained by asking the right questions. This isn’t about having regrets or wanting to change history, it’s about continuous improvement in a bid to become the best you. Here are five questions to consider and journal on, to make your future better than your past, no matter where you are right now.

What led me here?

Narrative fallacy is where disconnected elements seem to form a story when looking back. But here the story is what matters. When did x lead to y? How did your personal story unfold? Which moves were responsible for your biggest breaks, what decisions really moved the needle on your business? Who were the people that opened those doors and who are you grateful to have in your life?

An analysis on the contributing factors to your biggest successes and failures so far is golden. Seemingly random occurrences could hold answers to the true cause and effect of your success. Your story so far won’t change, but what you take into the next chapter could. Make it intentional.

What held me back?

Instead of what helped you advance, what hindered your progress? Which opportunities did you narrowly miss and why? When did you think too small, ask the wrong person for advice or just play it too safe? If you had the time again, what leaps would you take? How would you have built on your foundations in a different way?

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 might have cost you more than you realize. Work out what held you back to remove it from your future.

How could I have done better?

Past you was young and naïve and future you is experienced and wise. Current you is navigating the journey between the two. If you’re not embarrassed of your past work it’s a sign that you’re not progressing. So what of your past isn’t good enough for your future? Where do you know you can improve and where have you already started doing so?

Which situations were you not prepared for, and how could you smash them next time? When did you feel that you hadn’t done your best, when did you sell yourself short? Unreservedly showing up is required for your next step. Where we’re going, there is no half-arsing it. Work out where you gave below your all so far and commit to nothing less than all-in going forward.

What can I learn?

The patterns of your past few years hold secrets, lessons and understanding. Picture your journey to date in history book form. Imagine a third party looking at the facts and drawing their conclusions. What would they glean and how would they make their appraisal? Pore over the events, go into the detail. Notice the trends of your actions turning into results.

Everything you did so far led to a result. If you want to change the results, you have to change the inputs. Learning the effect of the inputs comes by looking back and investigating. Work out what you can learn to take into the next few years. Start afresh armed with all that knowledge.

What should I change?

There are elements of your life and work to date that shouldn’t be carried forward. There are things you do every single day that aren’t serving you. Some people lift you up, others let you down, but unless you analyse, you won’t know which. This thought experiment involves imagining the changes you could make and writing a list. Next, project each list item forward. If you made the change, what would happen?

If nothing changes, nothing changes. You carry on the same and your progression is linear. But what about the exponential growth you’re so hell bent on finding? It’s discovered through change. Changing your geography, changing your company, changing your habits, appearance or disposition. All are up for grabs as you transform into an upgraded version of you.

Journal on these five questions to set up a sound future. Dig into the past to ask what led you here, what held you back, how you could have done better, and use what you learn to influence what you change. The old you brought you here but the new you will take you there, set them up for success in the best possible way.

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