Your Past Should Look Worse in Hindsight

I’ve been spending too much time lately worried about my narrative of the past.

When things have been hard, it can be especially tempting to want to hold on to a rosy vision of the past. You want to be able to pat yourself on the back for some things, after all.

It can be a jarring realization to find out that things weren’t as good as you thought they were. Maybe you begin to realize you could have worked harder. Maybe you find a massive gaping hole in your knowledge or character or skill set that you didn’t know existed.

This kind of uncertainty and doubt is bad enough in the present. It’s harder to consider for the life you thought you had tucked safely away onto the trophy shelf. But this is just what happens with time – if you’re growing, you realize weaknesses and insufficiencies and gain perspective.

Still, it stings. What is the meaning of all that struggle if it only becomes less satisfying with time?

The meaning of the struggle is to get you where you are now. And the meaning of the struggle you have now is to get you to where you will be. And all of this movement from worse to better is a sacred striving for the best within you (H/T to Ayn Rand) and the best within existence. To live and move and have your being in that flow is your reward – not to dwell on an idealized past. 

If you are living in the flow of growth, your past should look worse in hindsight. You can still be proud of the attempt, but you should come to view the achievements as less and less significant. Your business is in the present, and your achievements are going to be higher – if you can let go of the little ones.

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James Walpole is a writer, startup marketer, intellectual explorer, and perpetual apprentice. He opted out of college to join the Praxis startup apprenticeship program and currently manages marketing and communications at bitcoin payment technology company BitPay. He writes daily at