My Biggest Regrets

I had my 10-year high school reunion this past weekend and it got me thinking about my biggest regrets.

I have to admit I didn’t really want to go. I cherish my weekends because I only get 2 out of 7 days with my son. By the time Friday rolls around, I’m burned out and just want to stay home. Anyway, I had one thought that motivated me to go: “Janey, you never took the time to get to know these people while you were in high school. Do it now. You are talking to people outside your circle, learning new things; how could that ever can be a waste of time?!”

That triggered other thoughts about my biggest regrets and what I would tell my younger self. Then, coincidentally, I listed to Amy Porterfield’s interview of Sheri Salata, Oprah’s Executive Producer, and she had a very similar message! I found myself writing down everything she said and I felt the urge to share with you! [I also got to see Sheri Salata speak in person, which was amazing. If she’s ever in your area, I highly recommend going to listen to her! She is so funny and witty and is able to relate to everyone in the room.] So I intertwined a few of my regrets with hers:

What I would tell myself…

In High School

Spend less time studying and more time trying new activities and talking to different people. I graduated with 90-some people and I only knew 10 of them really well. I didn’t even know where half of them lived! I was SO focused on school. I knew I had to pay for my college education so my goal was to get as many scholarships as possible. I would stay up until 2am studying, on the regular. I wish I would have studied a little less and spent more time LIVING! Looking back, those were the easiest years of my life and I wish I would have just relaxed and enjoyed my youth.

In College

You have the rest of your life to work! I was paying for my rent and tuition so I always had 2 jobs, sometimes 3, at a time. I wish I would have lived at home to eliminate the rent expense altogether and then I wouldn’t have had to work so much.

As for my major, I go back and forth on whether I would choose something different if I could go back in time. My mom told me, “Time is money; get in and out and do not change your major.” I’m glad I received and followed this advice. I chose to major in finance so I could easily get a job. However, I didn’t really enjoy finance. I loved psychology and sociology so I did a double-major in human Resources to fulfill this interest.

Do you think you really needed a college degree to get the job you have now? That’s the question I ponder with colleagues and friends. For most careers in business, you absolutely need a college degree. In some companies, you need an MBA just to get a management position. However, I saw a lot of successful people climb the ladder without business degrees. Getting an undergraduate degree was a must for me but I can understand it’s a tough decision for creatives and entrepreneurs to make when college tuition is over-inflated. While I wish I would have worked a little less in college, I fully believe you need to have work experience when entering the workforce, regardless of the industry! I see too many college graduates with no work experience. Here comes some tough love: there’s no excuse for this. Why would anyone hire you if you have absolutely no experience?! It doesn’t have to be the perfect internship. Start small and take the next step, or the next job, that gets you closer to your desired field.

At 22

This may be a beautiful no or an unanswered prayer, you just don’t realize it yet. Trying to find an internship or job is excruciating! There’s a catch 22 where the employer wants you to have experience but you just need to land that first job in order to get experience! As I mentioned above, that’s why it’s important to start small with a job in high school or in college. From there, you can take baby steps to get to your dream career. Also, don’t feel bad about job hopping! For me, that was the only way to get a raise or promotion. The financial services industry is notorious for hooking college grads on a higher-than-average salary and then not giving those employees a raise for several years. You have to do what’s best for you!

At 25

Set the bar a little lower. Don’t put a deadline on your dream. For some reason, I thought I had to be married, have 2 kids, have a master’s degree, and be a manager by the age of 30. I remember hitting 24-25, and being a little disappointed. I wanted to change the world and here I was living the life I swore off: 1 of 30,000 employees; just a checked-out zombie keeping her head down and slaving away.

Sheri says it better than I can: “It takes courage to choose to dream rather than continue down the same path. You can always start over. It’s never too late to make your dreams come true. If not now, when?” As Sheri explains in her book, The Beautiful No, she tried several different careers, got turned down for a really good job and therefore took the entry-level position at Oprah at the age of 35! Trust God’s plan and have faith things are working for you, not to you. I was rejected so many times for jobs and promotions, but now when I look back, I’m so thankful I didn’t get that opportunity. I would not be where I am today if it wasn’t for that rejection.

At any age

Stop worrying about others think. When I was listening to Sheri at a conference, there was a moment the entire room was brought to tears, including me. I can’t quote her verbatim but she was talking about the moment her mother was on her death bed. As she held her mom’s hand, she could feel her reckoning with God and her regrets. Her mom regretted wasting so much time worrying about others’ opinions and would do anything for one more day. Wowza. Breaks my heart just to write this.

I used to be fairly confident and didn’t worry about what others thought of me. Then I became a mom. Suddenly I had no idea what I was doing. Where is the manual for this?! Everyone had a different opinion and approach to breastfeeding, sleep training, work-life balance, self-care, etc. And how did I handle that? Hopped on good ole Google and researched my life away; resulting in more confusion. I remember reading somewhere, “We research and seek input in the areas we are least confident in.” Yup, sounds about right.

I’d be lying if I said I don’t worry at all what others think but I’m getting better. The first step was to recognize I’m in a vulnerable place when I’m seeking others’ input and I need to be careful what I digest and listen to. Another thing that helps me reel in these thoughts is Rachel Hollis’ words of wisdom: “Someone else’s opinion of you is none of your business. Don’t let someone else have an expensive opinion on your life. You’re the one that has to live with your decisions, not them.”

What’s your advice for me?!

Alright, I have a lot to learn as I enter my thirties and God willing, have more children, and eventually go through the empty nest and retirement phase. So what would you tell someone in their 30s, 40s, and 50s? Feel free to comment below!