5 Life Changing Things I Wish I’d Figured Out 15 Years Ago

As I careen toward 40 I’m noticing that I have little tolerance for things not being done well, or being done haphazardly. It’s hard to explain. Coming of age in the early 90s in Vermont gave me a scrappy DIY mentality, and I had to be pretty creative about making my way in the world. I feel like I’ve spent the last few years filling in gaps!

I realize folks grow up a lot faster and with a lot more information at their fingertips now, but just in case:

1. Don’t just throw money in your 401K without looking at it. I haven’t fixed this yet but I did put together a plan with an advisor and I’m giving myself until the end of 2015 to implement. Don’t stick with the default funds. Know where your money is going and how hard it’s working for you. Research what works best for your goals, and balance the mix so that when you get to retirement, you have diverse buckets of income – pre-tax and post-tax. Invest at least 10%, especially with employer matches, and split between 4-5 funds max. Look at outside investing / having a retirement fund set aside in savings account to invest outside of your 401K.*

2. Buy things that fit you well. I finally snapped during work on Thursday while wearing a severely uncomfortable bra (seriously, this past Thursday, it’s taken me 25+ years of wearing bras to do this?) and had a sweet older lady at the lingerie shop tell me I’ve been wearing the wrong size for years – once she figured out the size and the best brand for me, I walked out feeling like a new person. My back felt so much better that I almost started crying with relief. I also recently bought sneakers to wear when traveling, because every single time I tried to wear cute shoes while traveling I got blisters and ruined my trip.** Don’t ever wear clothes or shoes that hurt, pinch, or make you focus on the clothes instead of what you’re doing in that moment. Learn what fits you. Know what that means. Get things tailored. Buy multiples of staples when you find something that you love and that is comfortable. Especially underwear and shoes. It makes life easier.

3. My great grandmother used to say “never pay someone to do something that you can do yourself” and my great grandfather used to say “never do something that you can afford to pay someone else to do.” Find the balance between the two. Figure out what to outsource, and what you want to tackle yourself. Cleaning. Cooking. Gardening. Car maintenance. Home renovations. Blow outs. Some people just hate to clean and would rather spend the time doing other things, so the expense of a housekeeper is worth it. Other people want to save money and learn to be self-sufficient, so they DIY home renovation. But you can outsource basically anything, so don’t spend your life doing things you hate. If you DO decide you’re going to do it yourself, buy the best tools possible to get the job done well and efficiently.

4. It might be your job, but it’s not your problem. I am someone who throws myself into work 100% and I need to remind myself to step back and not internalize when things don’t go as they should. That doesn’t mean I don’t do my job well or have empathy & compassion for the situation – it just means that it’s important to create healthy boundaries when things at work get stressful, so that I don’t internalize or bring it home.

5. Prioritize making friends when moving to a new place. I’m still getting my friend fix in when I travel or through texts across the country, and now 4 years into being in Vermont I’m like “shoot, I need to make some local friends.” It’s really, really awkward.

Stay tuned for the life changing things I DID figure out 15 years ago, I didn’t spend my entire 30s bumping around like a lost kitten.

What’s on your list?

* Talk to a financial advisor. I am not one. But if you’re coasting along like I was, this might be a good place to start & a starting point for questions to your financial advisor.

** See photo illustration for life lesson 2a, trips ruined by broken feet can be redeemed by sitting for hours in the Plaza’s Champagne Bar and letting waiters bring you everything you need. They’ll even charge your phone for you. 


  1. Yes! Love this! I find that I have absolutely no patience for uncomfortable clothing lately. That’s a tiny daily annoyance that I just don’t have room for in my life. I’m also really recognizing the significance of the mashup of #4 and #5 in my life right now. I live and work in a tiny town, and I really enjoy my co-workers, which means that my work and social lives are dangerously intertwined for my mental health. I need non-work friends!

  2. 2b: Get fitted for a bra more than just the once. Changes in diet and activity may not have changed the number on the scale or the size of your pants but they can change your fat-muscle distribution enough that your bra size changes. Somehow I lucked into the bra department in Nordstroms as a high school kid and learned the glory of a well fitting bra but I’ve neglected to go in and get resized in the last three years. :-(

  3. 2000, just moved back to SF… the things we wore back then while trying to figure out who we were thinking we knew it all. I think my clothes were too big for me.

    I would add “use all your vacation” and “getting laid off is not the end of the world”.

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