Lynsay Hilsabeck

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Lynsay Hilsabeck, 33
Lives in: Portland

Lynsay Hilsabeck’s life is full and happy and refreshingly unconventional. When we met on a bus in Madrid in 2011, Lynsay was 29 years old. She was a successful career woman with a quirky sense of humour and a teenage daughter that she was raising on her own. Four years later and Lynsay has a second child, is happily married and recently uprooted her life in Phoenix, Arizona, and relocated to Portland, Oregon, her soul city as it turns out.

Though we can all say that life is made up of very distinct chapters, each different from the last and almost always outside of our expectations, they don’t typically unfold in the same quick and surprising succession as they have in Lynsay’s life. Her career developed whilst raising a daughter on her own, amidst changing relationships and finding her way.

Now, at 33, Lynsay is wholly centred and wise beyond her years. She appreciates fresh air, sunny days and margaritas in backyard bars. But, most of all, she loves her family and the time she spends with them.


Lynsay Hilsabeck, how would you describe yourself now as opposed to yourself ten years ago?

What comes to mind first is: less cautious. I remember being pretty scared of a lot of things in my younger days. Scared of conversation. Scared of doing some things the wrong way, making the wrong choice. I had a really difficult time deciding which way to go if there was a fork in the road. I worried a lot about what the consequences would be if I did this or if I did that. So a lot of the time I would shy away from a situation or not go towards an opportunity because I was afraid of the unknown.

Now I try to take certain risks. Obviously I have a family so I can’t be skydiving or anything like that! However, I read somewhere that the longer you try to ignore something the more power you give that thing and the more fear you have towards it, until it becomes more of a monster than it actually is. I try to address my fears and take things head on now. I would also say I am a better and more loving parent, I am a much more patient person. I have tried to slow down and enjoy life and not freak out about things.


My life was in a strange sort of limbo.
Self-discovery and advocacy
had not sunk in.


Lynsay (left) with her two beautiful daughters, Sierra (middle) and Phelyn

Lynsay (left) with her two beautiful daughters, Sierra (middle) and Phelyn

What were you doing with yourself ten years back?

At 23, I was already married. I was married to my now ex-husband, trying to have a perfect family life, trying to make house and home. It was the weirdest point in my life. I almost feel like I was a completely different person and I sometimes forget about that phase in my life. I got married when I was 21. I grew up in a very Christian household and I had thought that in order to get out of my parent’s house I needed to get married. Even though that sort of commitment was not good for me at that time, the guilt of religious influence and my parents led me into decisions at a very inappropriate time. It wasn’t the right choice for me at that time. My life was in a strange sort of limbo. Self-discovery and advocacy had not sunk in.

Quite a bit has changed since then. I think more about myself, about what I want, and I take care of myself more and, in turn, I’m able to take care of the people that are around me.

Obviously you had your first daughter quite young, so whatever plans you may have had as a teenager changed. What has your career ended up looking like?

Well, I had my first daughter at sixteen and graduated from high school early. I started college right away and was able to take some classes but I really wasn’t sure about what I wanted to do at the time. So I went to cosmetology school and did hair for four years, which was fun, but I was still all over the place as far as what I wanted to do.

I ended up going back to school about five years ago, it took me four years and I got my bachelors in psychology. I had every intention of going back and getting my masters, I really wanted to work with kids or with troubled teen mums or something like that but I ended up sticking with a job that I had gotten a few years earlier. It was a corporate job for an I.T. reseller company and I stayed there for eight years, all throughout my college. I got divorced in that time, a lot of things happened.


I’m just not a very good bullshitter.


I was comfortable in that job. It was good money, they kept on moving me up, giving me promotions. I didn’t really feel like I wanted to leave and I felt like it was my fall back. It allowed me to be successful in my own way, moving up in the ranks made me feel pretty good but then towards the end I felt suffocated. I was drained of all creativity. It was pretty awful so I knew that I had to make a move and get out of where I was. I wanted to get away from managing people. I was really over managing people.

Why’s that? What did you find difficult about it?

The politics. I couldn’t deal with the politics because I’m honest to a fault. I always say what’s on my mind, I’ve never been good at holding my tongue, staying quiet when I should. I would always just blurt out my feelings or say something to the wrong person and give them the wrong impression and I never really cared. Honestly, I just always said how I felt and I was able to continue to move up but only to a certain point. I never wanted to be involved in anything higher than where I was…like director level or anything like that. I’m just not a very good bullshitter. I think that’s probably where it all lies.

That’s something to be proud of though, I think. Did you feel like you fitted in?

I feel like the reason why I did well there is because I connect with people on a personal level. My teammates always came to me with issues regarding work but also issues regarding their personal lives and I really, really loved that. I think that’s really where my speciality lies, communicating in a raw form with people and not on a business level. I would put on my ‘suit’ and, you know, talk this and that but I just I hated it. It was so boring to me. I had a hard time with that sort of thing, but I did a good job and I think that I was able to continue on the path going up mainly because of my relationships with people.

Sisters: Sierra and Phelyn

Sisters: Sierra and Phelyn

You and I met in Spain on what, I believe, was your first month away from your eldest daughter? 

Actually, it wasn’t my first month away from her but it was my first month away from the States. She actually, from the age of nine, started to go back to her home state where she was born to visit her dad for the summers.

Was Spain a big turning point?

Yes it really was. Earlier I talked about fears and one of my fears is flying, another one is being alone or rather travelling alone, you know not having someone there to help guide me, and another one is the ocean…flying, then flying over the ocean to travel on my own was terrifying. It was pretty big but I enjoyed every second of it, I wanted to put myself out there.

That particular year a lot was going on. At that time, Wesley (my husband now) and I had just gotten back together after a nine month break-up. So a lot of stuff was going on and I was about to turn 30.

It was very big for me. It was definitely life changing. Getting away from your specific lifestyle, your country, your culture, your everything and stepping outside of that and learning somebody else’s and respecting somebody else’s was very eye opening.

Since then you’ve gotten married, had a second child and moved states. There’s been a huge amount of change in your life. What are you doing now?

Well, the last year that I spent in Arizona my husband and I just really wanted to get out. It’s a beautiful place but we were just ready to find somewhere that we could settle down and possibly buy a home. We had all of these of questions, like, ‘If we were to do this and this and this, where would we do it?’ It wasn’t that we were necessarily ready to do it at that time but we wanted to plan it out, get moving and also stop burning our hands on the steering wheel in the summer because it was so hot!

We ended up moving to Portland, our whole family, and we absolutely love it.

I have to tell you this one story, though. So we walk into our apartment for the first time, after travelling all the way up the coast with two dogs and a cat. It’s gorgeous, it’s hardwood floors and we have a gorgeous giant window in our front living room. We open up the window and we’re about two and a half stories up. We check out all of the other rooms and come back into the living room just in time to see our dog jump out the window!

Oh no!

[Laughs] Yeah…he just flies out the window.

What?! This story ends ok though right?

It does. So luckily he still has his leash on [laughs] and I fly across the room and I catch the tip of his leash. So he is dangling out of our window on a leash, right in front of our neighbour’s window below us. So it was a very emotional five minutes. There was the extreme excitement of seeing our amazing new apartment in Portland and then all of a sudden, Oh shit, my dog just jumped out the window. So I was laughing and crying at the same time because it was so intense.


Life and the universe
have been very kind to me.


Lynsay’s husband, Wesley, with their daughter Phelyn and dog Kitsuné

Lynsay’s husband, Wesley, with daughter Phelyn and dog Kitsuné

We found out we were pregnant in October, after we’d been here a couple of months, and I had a really great pregnancy. We had always talked about getting married but with what I had gone through before with my previous marriage, I just didn’t really see the need for it. But when I think about it now I like being married, in fact I love being married. I like calling Wesley my husband and having this little family unit. It’s been a wild and crazy ride since we’ve arrived in Portland: baby, marriage, we bought a house, but it’s been good. Life and the universe have been very kind to me.

So you’re in a very happy place right now?

I am and it feels really good to say that.

What’s your typical day like these days?

I work from 6am-3pm. Both Wesley and I work at an I.T. security company, he works in marketing and I work in finance. Working 6am-3pm is great for me because I get off early enough to pick up my daughter from play school (I call it playschool instead of day care because it makes me feel better). I love my job, I love the people I work with, I love the management.

Great! And now on to a bigger, more general question. What, in this whole life of yours, has surprised you the most?

The maternal instinct that I have with my second daughter. I did not have that with my first because I had her at such a young age and I was just incapable of having that yet. I was too young and didn’t really know how to feel that or act on that yet. Of course I loved her but had no idea what being a mum meant. I think I was probably enabled by my parents a bit too because my mum just totally took over where I left off. She was in love with my daughter and helped me out so much. And then having my second daughter, I didn’t anticipate feeling that way about something / someone. It was pretty amazing and it continues to grow every single say. So I would say that’s one of the only things that has really surprised me.

And the reverse of that, what has let you down? 

Hmmm…you know school loans really get me down. [Laughs] Seriously. I have just started paying back my school loan now and it’s discouraging because there’s so much talk about, ‘Your government wants you to be educated, people want you to be educated, jobs want you to be educated,’ and it’s so difficult to get that education. They make it seem so easy but actually you have to take out loans and then at the end of it you’re indebted to them for the rest of your life. Having a daughter who is finishing high school in two years it’s hard not to have a negative view on that. I want to encourage and inspire her and unfortunately I’m not at the point in my life where I can pay for her college and that makes me sad. So I’ve really pushed for her to make sure she’s got good grades, hopefully scholarships can come into play for her.

So I would say that debt in general. But school debt in particular…I have this piece of paper to my name but it feels like I have a ton of bricks on my back.


As much as you might
want to stay in that moment,
the universe doesn’t.


If you had a chance to sit down in a room with sixteen-year-old Lynsay, what advice would you give to her?

I would tell myself not to waste my time on worrying. I remember going through some pretty awful break ups and they messed me up a little bit and it was such a waste of time. Love and broken hearts are awful but time heals and that’s one thing I wish I didn’t waste my time on.

And to prepare for things. I wish I had saved more money. I wish I had gone straight through school without wasting so much time. And to enjoy myself a little bit more and enjoy my daughter at that time a little bit more too. I would say all of those things. There are many things I thought were important that were absolutely ridiculous which of course is a learning experience in itself.  So at the same time, I would tell myself not to avoid too many things because I wouldn’t learn.


I think that women have magic.
We’re magical, multi-dimensional
and complex.


Do you have any regrets at all?

I think that I do have a couple of them but I feel that I know that those things that I regret also shape the kind of person that I became and that they probably helped me avoid more mistakes in the future. So in a way I have learned to embrace them and love them so I try not to regret too much because it absolutely consumes you. I don’t want to be the person who continually talks about what went wrong or what someone did to me. Life goes on. As much as you might want to stay in that moment, the universe doesn’t.

Ain’t love grand? Lynsay’s husband, Wesley, and daughter Phelyn as a new born.

Ain’t love grand? Lynsay’s husband, Wesley, and daughter Phelyn as a new born.

What’s the best thing about being a young woman?

I think that women have magic. We’re magical, multi-dimensional and complex (in all the good ways). When you look at a woman straight on, you see one thing, but if you look at her from the side, you can see all the layers there are to discover. We play so many roles in life: mothers, sisters, daughters, creators. Powerful, powerful people in all kinds of positions but despite all of this we’re still doubted, and fight so hard to protect our rights, bodies, opinions, and that makes me sad. There are a lot of political things going on right now that demonstrate that we still have a long way to go. We have voices that are breaking through slowly. But to me, the best thing about being a woman is: we’re just magical.

And lucky last, our favourite Friday Best question, what do you think we should talk more about?

Animal extinction. I don’t know about you, but this scares the shit out of me. When it comes to this topic, humans are just plain evil and stupid. There is absolutely no need any longer to hunt and kill unnecessarily. We, as a species, have run so many beautiful creatures into the ground because…well, we just can. It’s frightening to me that people just don’t care, or look the other way. It is certainly easy to do so. But there’s so much we can do! We make choices every day that effect these practices: what we eat, where it comes from, what we buy, where we buy. Just ask the questions and do the research. Can you imagine a world without lions, and tigers and bears? Oh my!


Things I Love

Being a mum

I’ve been a mum for over sixteen years now. I
love my daughters to absolute pieces and they
keep me challenged mentally and physically
ALL THE TIME. The power we have to create
and mold these amazing little beings is
almost incomprehensible.

Living in Portland

I cannot say enough wonderful things
about the city I chose to settle down and
start a family in. Lush forests, greenery,
gardening, recycling, amazing mass-transit,
encouraged cycling in rain or shine, mom
and pop shops all over the place. This place
makes me feel like I can do anything and everything.

Weekend brunch

It’s more than just the food, you guys, it’s about
the experience. We love to entertain and have
people over to our home on the weekends.
Catching up with friends on happenings over the
week, talking about ideas regarding projects,
parties, life events. Life is about balancing
relationships, children, friends, work and everything
in between. Brunch is the perfect reason to do so!


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