Home » Things I Would Tell My 20-Year Old Self – #12 Jen

Things I Would Tell My 20-Year Old Self – #12 Jen

Welcome to another edition of Things I Would Tell my 20-Year Old Self! Today we have Jen of Connecting the Black Dots sharing some of the things she’d like to tell her younger self. I’m so happy to have Jen guest blogging today because I adore her. Even before I met her last year at Bloggers in Sin City for the first time, I felt connected to her – like she was someone I just had to know. Meeting her in person only confirmed this. Not only is Jen super cool to hang out with & Canadian (like me!), she’s a world traveller, loves dirty martinis and plays poker like a pro.


My favourite memory of Jen so far is the afternoon we spent wandering around Old Las Vegas drinking 99 cent margaritas and eating oversized hot dogs. It was totally awesome, however I’m really looking forward to hanging out with Jen again this year & hopefully making more great memories together that don’t involve questionable meat snacks.

I hope you enjoy Jen’s post as much as I do. Take it away Jen!

I remember when I was twenty and 30 seemed so far away. Now, my 29th birthday is rapidly approaching (less than a month away!) and I actually feel really good about it. I was so lost when I was twenty; just thinking about it makes me shake my head. I wish I could sit myself down and give myself a stern talking to, here’s what I needed to hear:
1. You are beautiful. Truly. You start recognizing this not only about yourself but about everyone else too. It sounds cheesy but it’s so true. I remember that time you cried because you ran into a girl you had known in elementary school and you weren’t wearing makeup. 20-year-old-Jen, give your head a shake girl. You will go MONTHS without wearing makeup and it will be the best damn time of your life.

2. That man-boy you’re dating is an asshole. You know this, and you’ll break up with him soon enough. Borderline abusive, he is damaging your self-esteem, your self-worth, and your relationships with friends and family. After you break up and move out you will have a really tough year. Very tough – you’ll even sleep on the floor for a month since you don’t have a bed and can’t afford to buy one. It’s okay, you’ll work it out and it will be worth it to be rid of him. Trust me.

3. You’re going to be single for a looooong time. You’ll date, you’ll have a pseudo-relationship, and you’ll be fine. But you will be single; I’m talking 7 years of single. You’ll love it, until one day you realize maybe you’re ready. You won’t settle and you won’t seriously date men who aren’t intelligent and kind. Maybe that’s the lesson you took away from the last one.

4. If you hate your job, leave. Yes, it looks good on paper. Yes, you feel very grown-up. Yes, you’re proud of yourself. But guess what? You are miserable. Going home after work and wallowing on the couch while eating ice cream is not healthy. Going out drinking all the time is not healthy. You’ll eventually get it together so don’t put so much pressure on yourself.

5. You also go to university, so stop stressing that you’ll never do that and P.S no one cares if you do or not except you. You ARE smart and stop acting as though you aren’t.

6. Remember that ‘best damn time of your life’ thing? After leaving the job you hate, you move to Central America, then to Eastern Europe and it’s all fabulous. You should have done that earlier.

7. Work on that temper! Being an Aries and a redhead do not help you out in this category, but try. You get much better at controlling it but it still flares up now and then. Keep calm; it’s never the end of the world.

So just know this, 20-year-old Jen, you’re braver than you think and you’re more fragile than you think. You make some pretty stupid mistakes but you also make some pretty good decisions. At 28 you’ll be happier, calmer, slightly wiser, healthier and overall more well-rounded. Just one more thing: laugh more, cry less, hug lots and be thankful for the people who love you.

What would you tell your 20-year old (or younger) self?

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