Jared White Photo of Jared

Expressively publishing on the open web since 1996.
Entranced by Portland, Oregon since 2017.

Getting Past the Pain of Starting Over

This is your chance. This is your time.


#mindfulness #lifehacks

This essay is over four years old. It's possible my views have changed since I first wrote this, but I choose to leave it online nevertheless. Cheers, Jared

At various points in your life, you will have to start over from scratch. There, I said it. It’s not the most pleasant idea to contemplate. It’s not really something you get as a pep talk when you’re entering adulthood. It’s not the sort of inspirational speech you look for when browsing TED.

There are so many reasons why you might find yourself in the midst of a total reboot. Maybe it’s a switch to a new career. Maybe a long-term relationship has ended and you’re wrestling with the prospect of singlehood. Maybe an artistic passion project just fizzled out (again). Maybe you ran into financial difficulties and needed to downsize dramatically. Maybe you finally graduated from college, yet your life’s purpose remains a total mystery.

Whatever the reason, the overarching existential question of So What Now? can feel debilitating. Suffocating even. The feelings of inadequacy, imposter syndrome, or perhaps abject failure can loom large. At times like this, it can feel like everyone else is more successful than you. I mean, that guy’s photo of his slobbering dog has a thousand likes on Instagram. Yours has one. That girl is swimming with dolphins and drinking mimosas and living her dream on YouTube. You’re wondering how to stop swimming in debt.

This is the road to madness. In my—ahem—comprehensive experience in such matters, there is only one path out of such psychic toxicity:

First, don’t try to hide from the pain. Face it square on. Embrace your emotional vulnerability. Feel. You will remain forever stuck if you refuse to validate and accept your inner life, for better or worse. If you were raised in a household where overt feelings weren’t openly shared or celebrated, I encourage you to seek a worthwhile method of life coaching or therapy.

Second, acknowledge that each successful person started their journey from scratch. Sure, there might be a rare exception here or there to this rule, but for the most part, everyone started at ground zero once. That pop star didn’t have a million fans when he started writing songs in his bedroom. That tech CEO didn’t run a hit startup when she first learned how to program in Ruby.

Third, it is never too late for you to begin. For the older genertions reading this, you might be wrestling with the inner demons of ageism. Oh, if only you’d embarked on this endeavor when you were 25, instead of 45. Or maybe you think you have too many responsibilities now, and the idea of focusing on a grand new project is simply too daunting. Well take heart! There are scores of stories about people who became truly successful later in life. Sometimes middle age is the perfect time to throw caution to the wind and reinvent yourself.

Fourth, learn to have fun along the way. The constant worrying about if you got what it takes to succeed, always comparing yourself to others, wallowing in self-pity over past regrets and failures…these negative habits will rob you of any joy and keep you down. I struggle with these kinds of doubts all the time, but I’m really trying to remember my mindfulness techniques and focus on the present. Look for opportunities every day to experience wonder, to open yourself up to unexpected delights, to connect with people and places which bolster your sense of worth and hope for a brighter future.

Fifth, remember to spend your mental resources wisely. It can be tempting to reinvent yourself in too many directions at once. One journey ends, another begins…and pretty soon you’re rethinking everything and everyone in your entire life. In times like this I have to remind myself of one of the tenents of essentialism as explained by Greg McKeown: “Everything changes when we give ourselves permission to be more selective in what we choose to do. At once, we hold the key to unlock the next level of achievement in our lives. There is tremendous freedom in learning that we can eliminate the nonessentials, that we are no longer controlled by other people’s agendas, and that we get to choose.”

In that spirit, I encourage you to take this opportunity—if you are faced with the prospect of starting over in some facet of your life—to choose. Choose to push past the existential dread, past the endless FOMO, past the notion that you’re “too late” to achieve your vision. Choose to embrace this new season of life and be thankful that you do get to start over. This is your chance. This is your time. As a wise girl named Anne once remarked: “Isn’t it nice to think that tomorrow is a new day with no mistakes in it yet?”

(Speaking of starting something new, I’m drawing cartoons now. This article is my first public attempt. 😄)


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