A Woman’s Work: Samantha

Samantha is my baby sister, but she’s not a baby anymore.  She is thirty, a new mom, and an entrepreneur, although she probably hates that term.  Sam was born when I was just shy of my 8th birthday, so I’ve always thought of her as little.  She’s not though, she’s a full-fledged grown up.  (She probably also hates that term!)  It’s really amazing from my perspective as the big sister to look at how she’s made these unexpected and really cool decisions about what she’s going to do and how she’s going to do it.  She just impresses me. 

She’s not necessarily doing something she expected to do, but she’s doing something she loves — which is way more important.

1) What is your job?

I am a new mom, and also one of the owners of a restaurant called Dillon’s Local in downtown Plymouth, MA.

2) How did you wind up in that job — was it something you always wanted to do, a career change, etc?

I double majored in history and political science at Umass Amherst — and I have the student loans to prove it — but after college I worked for years as a bartender and waitress.  I was employed at so many different places, and always thought I would eventually leave the service industry, but I was having fun and not ready to stop doing what I was doing and look for a 9-5 job.  I figured I would use my degree eventually, but the longer I worked in restaurants and the more I learned the intricacies of the business, the more I fell in love with it. I did not, however, love working for absentee owners or in huge restaurants with way too many employees. While working at a nearby bar & grille, I met my now-fiance, Colin.  Together we decided to try this whole restaurant thing for ourselves. For years we essentially ran bars and restaurants for other people…so we figured, why not do it our way?! 

3) What other jobs have you done in the past?  What was the path that brought you where you are now?

In high school I worked at Dunkin’ Donuts, then during and immediately after college I worked at low-paying or volunteer internships and I substitute taught for a while.  But I always had the bar industry as a fall back — it’s hard to walk away from leaving work with cash in hand and switch to waiting for a paycheck!  I worked at small bars, huge restaurants, dives, fine dining establishments, and everything in between. One year I worked at at least five different places. I was sick of bouncing around, and so was Colin. So we worked together and saved up all our money and took the risk!  We are now co-owners of our own place (along with our Head Chef), and we work for ourselves and do things the way we think they should be done.  But, just to complicate our venture, I found out I was pregnant about one month after we opened our restaurant.  Surprise!  Colin and I had to shift gears a bit — we went from opening a business and a follow-your-dreams mentality to working for something even more important: our son.

4) What do you love about your job?

I love everything about my job — both jobs!  I love being a mom, even though it’s still new to me. John Francis is only 7 months old so I am definitely still learning.  My outside job is the most rewarding one I could have ever imagined for myself.  I never thought I would be a business owner, but it suits me (and Colin) well.  I get to socialize and talk to my friends and strangers all day.  I get to run a restaurant with my partner how we think it should be run.  It’s nice not to have to follow someone else’s rules.  We get to be creative and we get to set the standards ourselves.

5) Have you faced any challenges/struggles to get where you are today?

I was broke for years after college! I’m still broke, but it’s for a good reason now. Money is always a struggle, but when you do something you love it doesn’t seem to matter as much. Bouncing from job to job was torturous. Working for someone else was never what I wanted. I do not like to be bossed around!  So now that I get to make the decisions, I am much happier.

6) Has becoming a parent changed your perspective on work?

Becoming a parent has changed my perspective on everything in life!  Gone are the days when I came first.  Now everything I do is for my little guy.  I’m still up all night, but it’s a much different scene.  I went from a pretty carefree existence to one that is way more worthwhile and I wouldn’t change a thing. 

7) What advice or inspiration can you give to other women — about anything — jobs, work, family, parenting, life in general — what do you want other women to know?

I’m new to the whole mom thing, but so far I think the best advice I’ve received is to RELAX.  I’m going to mess stuff up in work and at home, and it’s going to be okay.  I’m still struggling to balance my schedule, so I’ll take any advice I can get on that!  I’m pretty much winging it…but so far it’s going pretty well!

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Sam is managing a crazy new life in a pretty chill way — in the course of a single year, she became a self-employed business owner AND a new mother.  But she is happy and content and confident and it’s so clear that she loves her life.  Even when things get stressful, she gets over any momentary freak-outs, straightens up, and moves on to make things work.  And you know things can get stressful when you’re running a business and taking care of an infant!  (In my highly unbiased opinion, though, John Francis is basically one of the sweetest and cutest babies ever to grace the face of the earth, so that has to make things easier!)

The thing that makes me happiest reading Sam’s words is this: “Money is always a struggle, but when you do something you love it doesn’t seem to matter as much.”  It is absolutely true that doing something you truly enjoy makes all the hardships worthwhile.  And I love seeing my sister so happy and so fulfilled. 

And you guys, Dillon’s Local is seriously awesome — right on the water in Plymouth, MA, it’s a cool, cozy, unpretentious place and the food and drinks are seriously AMAZING.  They’ve already won awards for best local bar and been featured in the Boston Globe and at the Phantom Gourmet Food Festival at Fenway Park in Boston.  So not only are Sam and Colin happy, they’re also killing it in a very competitive industry.  I’m so proud of them both.  If you’re ever in Plymouth, MA, you should totally go eat there.

Thank you Sam for taking the time in what I know is an insanely busy life to answer these questions!

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Do you know someone I should interview for “A Woman’s Work”? Shoot me an email at

jessica@littlenestingdoll.com and let me know.

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4 thoughts on “A Woman’s Work: Samantha

  1. Alexis

    Loved reading this and getting to know your “baby sister” a bit more. I wish I lived close enough to try their restaurant, too!

    Reply
  2. Jane

    This makes me feel old!! Super impressive though, and if I can get a night out I would definitely try her restaurant.

    Reply

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