Bobbi made The Escape

Today Bobbi is here to share how she left her job to build a fun and fulfilling business of her own!

How Bobbi made The Escape

Tell us about yourself and what you do

I’m Bobbi! I’m a freelance web designer and social strategy consultant!

I’m lucky that I get to do something that I love while helping people make serious moves and a lasting impression with their businesses and blogs. I fell into web design accidentally, really, but doing so has had such a positive impact on my life and career that I wake up daily feeling so thankful that this is how I get to spend my days.

My spare time revolves around reading, crochet (don’t laugh), and trying to convince my fiancé that we should have a Harry Potter-themed wedding!

How long ago did you make the escape?

It’s so scary to think about this now, but way back in 2009! How has it been that long already?!

What roadblocks did you face when preparing to leave your job?

I didn’t face any roadblocks, really. I wasn’t living up to my potential, I was incredibly frustrated in my role, and I desperately needed an escape and a re-evaluation of what direction I wanted to take, so I made it happen.

How did you know you were ready?

When I booked a plane ticket to England to stay with my sister for a few months! It was coming on winter and we had plans to take a few trips while I was there, it just seemed like the best way to reconnect with myself and what I wanted to be doing, Eat, Pray, Love-style.

What is the best part of being your own boss?

It is so, so cool and empowering to know that you drive your own destiny. My business being successful is directly tied to how much I pour into it and I know that when I book a project, not only am I about to help bring someone elses vision and passion to life, but I’m doing something concrete for my future. It’s a pretty great feeling! I know, “I get to wear jammies while I work!” is a big selling point, but I take it really seriously and am grateful that I have the opportunity to make the decisions and create the services and products that are driving me forward.

What challenges have come up?

Honestly – a lot! But, that’s how it goes and you’ve got to work with what comes your way. Once I got a handle on saying, “No,” life got much easier! I think that being someone who naturally wants to please, I had a hard time setting boundaries and setting realistic objectives for a long time. That made for a lot of sleepless nights and feeling as though I was falling behind, but then I realized what was going on and made steps to set my business up in a way that makes sense and is productive and fulfilling for both my clients and myself.

I think that being kind to yourself is 100% the fastest way to facing challenges head on and finding solutions in a positive way.

What are your work days like now?

Every day is different, but there’s a structure there, if you dig deep enough. I’m generally answering emails before I get out of bed (I know, bad). Once I’m up and have properly doused my brain cells with a healthy helping of coffee, I tackle the biggest things first. Anything that requires a lot of concentration, I take care of in the morning. Since I’m 5 hours ahead of the East Coast of the US, the mornings are my time to work in peace and get the big ticket items out of the day.

If I haven’t gone to the gym in the morning, I try to sneak it in around lunch time. If it’s raining and cold outside, I am unashamed in saying that I keep myself indoors where it’s warm with lunch and some reading.

After that, it’s back to work, wrapping up loose ends, dealing with inquiries, and working on side projects or taking a Skillshare class or doing some other form of development to keep myself up to date with what all the cool kids are doing these days. The time difference definitely keeps me on my toes; I’ll think I’ll be wrapping up at 6pm, but that’s only 1pm or earlier for my clients, so there’s usually a flurry of end-of-the-day emails that I like to take care of before I switch off for the day.

It can get hectic, but it’s fun, and I wouldn’t trade that for anything.

Thanks Bobbi! If you’d like to keep up with her check out her blog, portfolio, and follow her on Twitter.


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  1. says

    It’s so,so inspiring to hear success stories. I’m trying to make a success of my own freelance life, which has recently taken a turn for the better. I’m taking a web design class in grad school this semester and I’m excited to put those skills to use for other people after I finish the class.

    • says

      Megan – I’m so, so excited for you that you chose to jump! You’re going to smash it and I can’t wait to see what you do!! <3

  2. says

    I love Bobbi, I’ve been following her for a while now, and it’s great to hear about her whole success story in this post! I knew some info from reading her blog already, but it’s even more inspiring to read this and know how amazing everything has turned out for her!

    Thanks for this series, while I’m not nearly ready to start my own freelancing, I love these bits of inspiration to know that it is achievable in due time :)
    Memoirs of a Pilgrim

    • says

      Jamie, thank you for your sweet words!

      Sarah is amazing, I think that she’s doing a great service to the creative community with this series. She’s been one of my favorites for a while, I was honored that she asked me to be a part of this series! <3

  3. says

    Bobbi did my blog design too! The saying ‘no’, is such a difficult part for me in my Physiotherapy business too! Love this series :) Lulu

  4. says

    I love reading these “I Made the Escape” stories! And I’m planning that someday you will be featuring me too as a creative person who has made the escape from dreary office life. ;) My day job is actually pretty cool by most standards, but I’ve known for a while it’s not for me, and I’m on the path of exploring what IS for me. What I love most about Bobbi’s story is her “Eat, Pray, Love” style hiatus after leaving her job. Most “success stories” I’ve read are from ladies who are super-organized with multiple freelance gigs going on the side before they leave their day job. I think that’s fantastic, and obviously the most rational choice, but I myself am thinking about taking a little time off to travel and explore. I’m turning 30 this year, and part of me feels like I should have done that at 21, but again I’m turning 30 – not 90!! It’s always a good time to chase your dreams – no matter what age. (Hey even at 90 too!) Thanks again for putting these posts together!

    • sarah says

      I think a hiatus sounds like an awesome idea. I had a mortgage to pay, so I jumped straight into work, but if you’re able to take some time off I’d say go for it. You’re gonna work harder than you ever did at an office job when you’re working for yourself :)