37 Lessons in 37 Years by Jessica Taylor.

37 Life Lessons by Jessica Taylor: @your_datingstylist

I turned 37 a couple weeks ago, and I must say, I have experienced many things in my life. These experiences have shaped me into who I am today. Sharing this with all of you is as important to me as it may be to you. It is a road map of how far I have come in 37 great years and the amazing experiences that are ahead of me as a result of the obstacles I have been able to overcome. I think the most valuable lesson to date is that my biggest strengths came from challenges. If we focus on the things we have struggled with, it’s amazing what qualities stem from that. When I was younger, going back to 5th – 7th grade,  I lost my group of friends. They became popular overnight and I for some reason did not. At the time I felt lost, friendless, and confused. Why was I not making friends? I was picked on a bit and struggled during that time. Looking at who that made me now, I wouldn’t change a thing. I am extremely compassionate towards others, caring, nurturing and want people to feel at ease around me. This is just one small example. Life has taught me to be determined and to believe in myself. I took gymnastics and couldn’t learn how to do a back handspring which was all I wanted to do. The coaches would say “you’re not ready yet”! Well, I took their lack of belief in me and I quit gymnastics. But every day after school I would practice down a hill, often times landing on my elbows! until one day, my belief in myself got me to where I wanted to be. I will never forget the feeling of landing my first back handspring. I spent hours & hours till I finally achieved what I knew I could. I learned that you can’t have limiting beliefs – go after what you are capable of – even when others do not think you are ready.

Learning the back handspring also taught me about balance. This is key for me; working out, yoga, spin, walks and lifting. Exercise routines keeps my body feeling great. My dad has always been very into fitness and his continued motivation is what I aspire to be like. Working out helps relieve stress, it keeps you healthy and calms the mind. I try to eat healthy but always have a piece of dark chocolate every day.

Facing my fears is another lesson which I work on consistently. I grew up in a family that has anxiety and phobias. One includes something that most people dream of, TRAVEL.. yup. It’s not something I like about myself. I am a work in progress. I get very anxious flying and being in faraway places. In high school I was asked by a friend to visit England with her, without hesitation I said YES. I went and had an amazing time. This goes back to limiting beliefs – you have to challenge yourself – I CAN handle new situations. Do not give into your fears. Do not stay in a place where you aren’t happy. Whether that is in a relationship, school, or job. When you know you need to make a change, listen to that instinct. I loved many things about my college, but something always felt like it was missing. I am not someone who partied, I worked every weekend and studied hard. I wish I could go back in time and attend a school in Boston and live in the city. I think the interesting activities would have stimulated me more than beer pong in a dorm room. I wanted to visit art museums, coffee shops, meet people with some of the same interests as me. I don’t regret staying at my school, but it taught me – leave a situation if you aren’t feeling fulfilled.

This leads me to my divorce. Don’t change yourself or who you are, I never did that in my marriage. I knew certain things were missing but I wanted it to work out. He was a great person, but just not my person. It’s scary to start over. Especially since all my friends were starting families. But I learned from my college experience that you don’t want to be somewhere you aren’t happy. I took that leap of faith and started over. Starting over isn’t easy. However, my next bit of advice is always be open to making new friends & networking. I have had many job offers from relationships I have made over the years. I think resumes are great, but that personal connection allows you to stand out. When I moved back to Boston as a single girl I knew I needed to make new friends. I love the friends I have but I also recognized that I was in a different place. That’s when my blog Jessinthatdress.com – Now, your_datingstylist really took off. It helped me meet amazing people and attend so many great events around the Boston area. No one is going to create a life for you, you have to go after things – friendships, relationships and most importantly, goals. I have also realized that helping others feels good. When you can take the time to listen to friends, volunteer at an animal shelter or with people facing challenges, it’s the best feeling. I need to do more of this. It’s amazing how a couple hours of volunteering or a weekend activity can change someone else’s day. Such an easy thing for me to do!

I am the annoying friend that encourages my friends who are single to keep dating. It goes back to me wanting to learn back handsprings in my yard or making new friends. If you want something bad enough you have to go for it. I at times treated dating as job hunting. I felt that if I put minimal effort in, I wouldn’t achieve what I wanted which was ultimately a relationship. I have currently been dating someone for almost 8 months and its going great. Dating can be very difficult. Don’t let it ever make you feel like you aren’t worthy of love. I have had many bad dates, disappointments, I have been ghosted, love bombed etc. You know how it is out there if you are dating. But I always knew my worth. I knew that I would find someone that would treat me like gold. My dad & mom always gave me great advice, but my dad always said to me and girlfriends growing up, “You will KNOW if a guy likes you”. That simple message stayed with me forever. I never would have to question myself, or how someone felt about me. It would go without saying. It is the simplest advice but the most impactful.

I know I have shared a few lessons already but since this is 37 lessons, I have decided to list them out with hopes that someone out there learns and grows from this. So, here we go:

  1. Keep certain things personal – Don’t overshare with others
  2. If you are having a bad day – emotions are fleeting – base things on facts. Chances are its temporary
  3. Do not take anyone for granted
  4. No one can make you happy, but yourself
  5. Don’t be afraid to ask for help
  6. Go after what you want
  7. Try to find the positives in your challenges – this is where strength comes from
  8. Face your fears, get out of your comfort zone
  9. Always keep your interests while in a relationship
  10. Don’t settle or stay in a situation that you are not happy in
  11. Stay active & work out
  12. Keep making new friends throughout life
  13. Age is just a number
  14. Networking is sometimes just as good as sending out a resume (or better)
  15. Stay determined
  16. Try new things! This past summer I went to a roaring 20’s party… I also tried Zip Lining and loved it
  17. Know that change is inevitable – don’t fight it. The more you embrace it the easier it will be
  18. Keep learning, I took an entrepreneurship class at Babson a couple of summers ago
  19. Pay attention to what ingredients are in your products, less is more. I worked for a popular cosmetics company for 15 years and I constantly had parabens, talc and not such great things on my skin. I am very careful now and use organic & natural products when I can.
  20. Let go of things that are not right for you
  21. Forgive & move on but that doesn’t mean you have to forget
  22. Spend time with family
  23. Don’t gossip
  24. Find your favorite places to visit. Whether that be a special beach, cafe, or yoga class etc.
  25. Be with someone that respects you and treats you right!
  26. Learn from grandparents or people who have more experience than you
  27. Sunscreen
  28. Eat healthy – learn to cook
  29. Be comfortable in your skin, you are the only YOU – OWN IT
  30. Stay positive, even when times get tough or you are discouraged – look for the silver linings
  31. Do not compromise your morals or values
  32. Buy those shoes, or whatever it may be!
  33. Be kind to yourself, its ok to have a Netflix night!
  34. Stay youthful – It’s ok to have the sense of humor & playfulness
  35. Laughter & humor can carry you through hard times
  36. While dating – Lean back – the guy should lead!
  37. Don’t change who you are for anyone

Bonus lessons:

  1. Be your own advocate
  2. Music is great for the soul

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One thought on 37 Lessons in 37 Years by Jessica Taylor.

  1. Jess, You’ve come a long way, congratulations. Brave, raw, real, been there done that. Nice to know that we all go through something and come out the other side, stronger. A fantastic article

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