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Lifestyle Blogger | Biz Owner | Career Mentor

I'm Anna Osgoodby and I'm a creative business owner and lifestyle blogger based in Tacoma, Washington. By day, I'm in full girl boss mode running my business Bold & Pop with my seriously awesome biz bestie & Co-founder, Mallory Musante. Together we specialize in helping business owners and bloggers with their social media, branding, and Squarespace website design. By nights (and weekends) you can find me adventuring around the Pacific Northwest with my trusty weenie dog, Scooter and sharing my adventures on my blog.

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Growing up, I was always the girl with dreams bigger than I could imagine. I grew up in a small cow town in Washington, but always knew there was so much more to the world than that and was couldn't wait to break out and make something of myself. I didn't always have the details fully worked out, but I had a general plan and that's all I needed at the time. I had my college major picked out by the end of my sophomore year in high school, enrolled in our running start program to take college classes my junior year, my college major courses planned by my senior year and first first half of my 20's planned. Graduate college early, get into the senior experience program in Portland, explore that city for a few years, move back to Washington, work at a big fancy office in Seattle, buy a cute condo, get married at 23 (this one seems especially crazy looking back now), adopt a dog or two and live happily ever after.

And in those early days, my life was going according to plan. I graduated from high school with my Associates of Arts degree, boom 2 years of college done, was the first in my family to go to a university and got accepted to the college I wanted (Go Ducks!), and I cruised my way through my pre-major classes to get into the journalism program. Check, check and check. By my second year at University of Oregon, I was excited to apply for the senior experience program for seniors that allowed them to finish their last quarter of classes in Portland, while interning in the city and working on a campaigns class with an actual client. One app and interview later, I was in! Next up? Land an internship in the city. A week and a dozen applications later, I had my first internship interview. One drive to Portland and an hour later and I had aced the interview and was offered an internship on the spot. There was a heck of a lot of hard work in between but everything was going according to plan. Until it wasn't.

I finished up my last quarter of college in 2009 right in the middle of the recession and while my eyes were bright, actual career prospects were grim. I was the only person in my program to graduate with a job offer from my internship. It wasn't a job at a big fancy office, but it was a foot in the door to the industry and I was determined to make the most of the experience. It was a part-time position and I still kept my evening job at Safeway to make all of my bills but it was something. In 2010, my boss decided to move the office to NYC and offered me an opportunity to come along. I had only been to NYC once before, but decided to take a chance and give it a shot. It definitely wasn't apart of my "plan" but I was determined to make the most of my career and it seemed like a good opportunity. A month later, I boarded a flight with a one-way ticket to move 2500+ miles away to an apartment that I had never seen before (that was double my rent and half the size of PDX), with a roommate I had never met before. Sometimes I look back and think about how crazy that could have turned out but somehow it all worked out. At the time, I only planned on staying a year so I think the magnitude of it all just kind of floated away from me, plus let's be real here... I was 21 at the time.

I planned to stay a year, but that year became 2, 3, 5 and then 6 very quick. I was growing in my career, I had made some great friends, I had started this blog, oh yeah, and I had met a guy. After a few years in New York, my family came to terms with the fact that coming home might not be in the cards. I had build an amazing life for myself in the city that I loved, but those airport goodbyes never got easier and I always struggled with being homesick. Needless to say, moving home was kind of a sore subject in the family. So on a visit home for the holidays in 2011 or 12 (and after a few glasses of wine), I told my Mom that by 2015 I would have a plan for a career that allowed me to be bi-coastal and spend more time on the west coast. I didn't have a plan, heck, I didn't even have any ideas at the time, but the seed had been planted and the idea was always in the back of my mind.

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A few more years went by, I moved into my own apartment -- it may have been less than 400 square feet, but it was all mine and I felt like I was living on top of the world. I was repping some big-name clients, managing the social media department at the agency I worked for, making a solid salary, and getting some really great opportunities for my blog. While there were plenty of things that weren't perfect, things looked pretty good from the outside. By the time 2015 rolled around, the idea of being bi-coastal was still on my mind but I still didn't have a reallll plan. Until everything came crashing down. While I loved the work I did, and those I worked with at my job, the office I worked at had always had somewhat of a hostile environment. I had always been pretty lucky because I ran my own department, but as the new year began, it became clear that the target had been placed on my department. Having your job threatened was (unfortunately) a pretty common occurrence at the agency, but it was a new experience for me and it was not something I was going to get used to. So I started looking for other opportunities and interviewed at a handful of places before becoming bummed out that I just wasn't really finding anything that I loved. Queue that bi-coastal idea. I started talking with my co-worker about how I wasn't really finding anything I was excited about and how I really yearned for a job that offered more flexibility to be back on the west coast more, but the idea of freelancing freaked me out and how it would be great to have a sort of collective where we could work together on projects but also have the freedom to be on our own. To my surprise, not only did she love the idea but she suggested we pair up and make it happen. And for the first time, I realized... dang we could REALLY make this happen! A few months later things escalated further at work and when my boss told me she was going to lay off Mallory and was considering closing my department, I put in my notice too. It was time to put everything we had on the line and see if we could make this dream a reality.

So in December of 2015, with a few weeks left to spare, I kept my promise to my mom of becoming bicoastal and Mallory and I launched Bold & Pop -- a social media, branding and web design collective. I kicked off being my own boss by spending a month back in Washington and spent more time home in 2016 than I had the 6 years combined. I didn't know where this new path would take me, but the new found freedom of being able to spend more time with family was a game changer. Being a business owner has been one of the most challenging and rewarding experiences of my life. It's definitely a journey of a lot of highs and lows, and one that will truly test every ounce of your character, but it is a decision that I'm so happy Mallory encouraged me to make the jump. Because let's be real, having my biz bestie along for the ride is the true win! Helping fellow business owners and bloggers crush their goals and bring their brands to life, while also living out my dreams, is justttt about the best thing ever.

By the time 2017 rolled around, life was ready to hit me with another big curve ball. On one of my trips home, my boyfriend of almost 7 years and I decided to unexpectedly call things off. Like, just resigned our lease a few weeks before and now we had to try and get out of it unexpected. I never saw it coming... and while the thought of moving back to Washington full-time was something that was always in the back of my mind... it wasn't part of my new life plan. It was a weird time. On one hand, I was devastated to be ending this chapter of my life and saying goodbye to the life I had built, but on the other, also slightly relieved and excited to be back in Washington permanently. Life happens, and if there's one thing this planner has learned over the years it's that you can plan all you want, but sometimes there's a bigger plan for you and you just have to learn to roll with the punches. So after 10 years of living in a different state than my family, I packed up my belongings, hired cross-country movers and booked another one-way plane ticket -- this time to Washington. And this time I'm here for keeps (for real!). I bought a new car, moved into a new apartment, started some new hobbies. All of the newness! Life can be one heck of a journey and have some messy moments but as long as you are learning along the way, I've learned it's all going to work out one way or another.

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SOMETIMES YOU HAVE
TO LEAVE THE ROAD
TO FIND YOUR PATH

 
 
 
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Here are a few of my favorite things