Have you ever botched an interview so badly you considered switching careers? Or mindlessly stumble into an argument with a friend, which led to a falling out, so now you’re in the market for a new HBOGo password? Whether you royally fudged something up, or just acted more in the manner of a jack-ass than usual, it’s left you feeling in a funk with yourself–and not the good kind, Rick James.

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After a while that funk thickens to insecurity. Soon you’re doubting your every move, growing sensitive to every criticism, and using all that negativity you feel to fuel your life while dumping out the positive. You’re disgruntled, you’re discouraged, and you’ve a beef because of it with no one else but you.

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Whoa there, Bessie! Pump those breaks on all that self-loathing! There’s a better, healthier way to ease through those feelings of doubt, and it isn’t guzzling gallons of self-haterade. All it takes is a pen-pal, though not maybe the one you’re thinking of. Don’t get me wrong, I’m sure Jessica that fun-loving chica you clicked with at sleep-away camp circa summer of ‘98 would be glad to get a letter from you after all these years, but she’s not the one who can help you her. The pen-pal you need to hear from is you. Writing letters to yourself is a great way to shake off all that insecurity, and feel like the you you know and love.

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You don’t even need to burden yourself with a pen and paper. Shoot yourself a text, an e-mail, start up a blank word document, or an account on an online journaling website, like OhLife.com. Pull your plights out from the confines of your mind and put them to words in a letter signed to and from you. The result will build confidence in yourself, and aim your motivations toward a positive outlook and attitude.


Here are a few reason why self-pen-palling can wrestle you out of your doubtful funk, and into a cooler, calmer, collected you.

1. Put your problems on the page. Seeing your insecurities written in your own words helps extract them from your thinking. They aren’t doing anyone one harm in your letter, but if you let them seep in your psyche for too long they’re just going to wear your down to a low you never needed to be. The act of writing out that which plagues you most is stress relieving. The more problems you put on the page, the more space you open up in your mind for solutions.

Dear Me, Holy crapoli! Nothing I ever do lately seems to work out! Every campaign I take on seems to die right in my hands! I think I might be cursed… Actually, I know I’m cursed… I have to be… Why didn’t I send that chain letter to 10 other people? Who the hell even sends chain letters anymore? I need to get off that e-mail list… Haha, but seriously, who really does send those things anymore? … Wait a minute…thinking…thinking… IDEA… what if I—for the campaign—holy crapoli! Love, Me


2. Get the advice you want and need. When you’re feeling insecure or out of sorts, sometimes reaching out to a friend for reassurance can feel like your best bet in boosting your self-esteem. And while their encouragement may be well-meaning, it isn’t necessarily the advice you want or need to hear. There’s no guarantee the help they have for you can fill that void in your confidence. Only you can know the true root of what’s bothering you, so only you can uproot it.

Dear Me, Yesterday was a rough one, slugger. I know, I was there. Building rapport with a stranger can be tough, especially if that stranger could be a potential investor to get your website off the ground. That’s a lot of pressure. You might have come off as nervous, but your work speaks for itself. Trust that and trust you. Love, Me.

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3. The truth is in your text. When you write yourself a letter, there is no incentive to sugarcoat how you feel. Let the truth pour out, no matter how ugly it is. Extract all your anxieties and put them on the page. Face your fears head on, and bring them out into the light so you can see them for what they truly are, roadblocks.

Dear Me, Let’s take a side bar here because what I’m about to say may offend anyone and everyone that hears it… What you said out loud in that meeting the other day was perhaps the most incoherent, incompetent string of babbling bullshit I’ve ever laid ears on. There. I said it. You’re better than that, and you know it. We both know it. Next time take a beat then speak. Now we can move on, and we will. Love, Me.

you for you louie

4. Get your goals in writing and gain them in life. Self-pen-palling will help you to move past the worries standing in your way of achieving your ambitions. So while you’re listing off all those roadblocks, also remember to include what lies on the road ahead, your goals. Seeing your goals there on the page in front of you will make them feel more tangible, reachable. It will give you the drive necessary to put those words to action in your life.

Dear Me, Try to remember where you’ve been, and where you want to be. You’ve had four short stories published. If you can manage the math, young wordsmith, add up that word count and you’ve already got yourself a novel. Your creativity has sold before, so who says it won’t sell again? You’ve already proved your stamina, so put your creative brawn to work and manhandle this novel! Love, Me

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So reach out to yourself when you need it most with a reminder of who you are and how you feel. Getting your feelings out and onto the page is a great way to catch up on your correspondence the one and only and lovely you.


Since graduating from the University of Dayton, Mary has used her hard-earned education in becoming quite the dabbler in her twenties. She self-identifies as a writer, stand-up comedian, book repair specialist, mug collector, nanny, dancer, video editor, dog-walker, rugby player, and budding over-sharer. When she isn't defending the sanctity of boxed wine, she is usually out for a run against her will, or hitting up the dollar cinema for the latest indie comedy. Her favorite things are: Hogwarts, big dogs who think they're lap dogs, bare feet on a rainy day, Stephan Colbert, and comedic timing. If you want to find out what Mary's eating, or hear a far-fetched pun or six, follow her on Twitter @WrestleCrow or Instagram @wrestlecrow.

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