How I Left My 9-5: The Process

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I frequently receive questions and comments with regard to how I left my job and cubicle life to work from home and currently, not work at all (at least not in the way most people define “work”). I’ve been out of the SEO world for a handful of months, but it’s only been in the last few weeks that I’ve really felt I’m starting to have enough clarity to share more about how I made those big life changes, how things are going, and what the future might hold.

I’ll start by saying this: I did not quit my job overnight. It literally took me four years to work up to leaving, both from an emotional standpoint and a financial one. I’m a planner by nature and I have a hard time with uncertainty, which is why baby steps work well for me when I’m gearing up to make substantial changes.

Four years ago, I would have been completely unprepared to leave my 9-5, as much as I wanted to run far, far away. However, what I was prepared to do was to start making a case to be able to work from home. I accepted an offer with a company where, thankfully, this was an option, though not one the founders supported, and only for a couple of employees who lived out-of-state and were deemed valuable enough to retain. Seeing as how I had been an employee for maybe two weeks when I realized this, I made it my mission to prove my value over the coming months. Aaron and I also talked a lot about leaving Boston to try something new, which was the second piece of the work-from-home puzzle: getting out of state.

About six months and a lot of discussion later, we decided we wanted to try life in San Francisco and started seriously contemplating how we would make that happen. Shortly after, a couple of my fellow SEOs quit their jobs, leaving my employer short-staffed. I volunteered to take on some of the overflow work, knowing it would make me more difficult to replace. Around this time, I also received a very positive performance review, and so I nervously worked up the guts to confide in my manager that I was moving to California, but really wanted to keep my job (a calculated risk). With several of the company’s biggest accounts on my plate and solid relationships with all of my co-workers, he was understanding and accommodating. I began working from home as a full-time employee six months after I started.

Knowing my employer wasn’t completely comfortable with having me work remotely, I spent the next few months demonstrating that it was a non-issue. I had their biggest account at this time, and I used it as a way to show them I wouldn’t disappoint. It wasn’t easy and I didn’t love or even like most of the work, but I was hellbent on not going back to cubicle life, so I gave that account my all. That summer, the client renewed their contract for more than double, and shortly after, I started talking to my manager about switching to part-time contract work.

Going from employee to contractor was tricky, especially because the company had a firm stance on not allowing people to work part-time. Fortunately by this point, I was close enough with my boss that I could tell him I was thinking about pursuing culinary nutrition and writing, while still wanting to stay on as an SEO (he was again surprisingly supportive, because it turned out he was dealing with some health issues related to diet). I reiterated my commitment to the company and their clients, and agreed to keep all of my accounts until they could transition a few to other employees. This meant I was still working full-time for a while, but I was charging an hourly rate and actually making more money as a contractor, which incentivized them to bring my workload down to part-time.

To make things slightly more stressful, I became a contractor at a time when my company had recently decided they were going to stop using freelancers. The only reason I was able to convince them to let me make the switch was because I had over two years of good history with them, and again, I waited for a time when they were short-staffed to entertain the idea.

It was also around this time that I started blogging and putting energy into the things I enjoyed, while simultaneously phasing out the SEO. As a contractor, some weeks were busy and others were slower, and for the next few months, I mostly took on whatever work came my way to keep the peace. There was a short period where they cut my hours in half, which was scary financially, but it gave me the time and mental space I had wanted all along. For a while, I tried to convince myself that I could deal with this setup indefinitely, doing work I didn’t enjoy but on my own terms (sort of). This was short-lived and I started to realize I needed to get out completely.

You might think I would have continued to scale back my hours and push back on projects, but I did the opposite. When the company told me they wanted to contract me for up to forty hours a week, I maxed out my hours. I decided to make as much money as possible from January 2013 through July 2013 (when I finally gave my notice) to ensure I had a little bit of a safety net on top of our other emergency funds. Needless to say, the first half of the year was exhausting, trying, and ultimately, totally worthwhile. I made more money in those seven months than in all of 2012, all while staying committed to my blog and gearing up for the next phase.

It’s a lot to digest, but there are a few points I want to emphasize before I end this post:

Leaving my job took years of strategic planning, discipline, and patience. That’s not to say that what I did is what you should do if you’re looking to do the same, but don’t let yourself get bogged down in all the things that are preventing you from ditching the cubicle. Start taking small steps in your preferred direction, and over time, you’ll look back and realize you’ve completely transformed your life.

Seek out the things that will allow you to have the schedule/mental space/financial ability to work towards your goals. Sometimes life gets a little worse in the short-term to accomplish this, so try to look at the big picture.

Be on the lookout for opportunities, and when they present themselves, take them!Β There is only going to be so much planning and analyzing and worrying you can do. Life is uncertain, and staying in a joyless situation for the stability is not a good enough reason to stay.

I’m thinking I’d like to turn this into a series of posts, with the hope that my experiences might help you take on a big life change, whether that’s switching careers or just generally stepping off the beaten path. Next, I’ll likely talk about the financial aspects of leaving my job.

I don’t have it all figured out (far from it), but every day I learn a little more.



Leave a Comment

  1. I am looking forward to reading more! I don’t have a 9-5 job at the moment, but I know that eventually I would like to do something really flexible that allows for creatively and travel on regular basis. I will be really interested to read about the financial aspects of leaving your job! Thanks for sharing!

    1. Amanda says

      I agree, the flexibility thing is key. It’s really nice to feel like you have some say over how your day is structured.

  2. I am all for this turning into a series! I am on the same path, working in social media for a corporation at the moment. I’m not hating it, but I know that down the line I will want to leave to pursue my own dreams and goals. It’s a really scary concept, but I love that you are willing to share!

    1. Amanda says

      Thanks, Abby! “Not hating it” is more than a lot of people can say about their jobs, unfortunately. I think it’s great that you’re considering pursuing your own dreams down the road. πŸ™‚

  3. You must ave ESP….or there are enough like-minded people out there wondering how this is done!

    I’m busy trying to make it through the day at my 7 to 4, 5, 6, 7 as an engineer. Can’t wait to read this post when I get home. You’re an inspiration – thanks for giving me the hope that you really can “have your cake and eat it too”!

    1. Amanda says

      haha My bet is there are a lot of people who want out of their 9-5s. I still have a lot to figure out about how to make all of this work (especially financially), but I’m happy to share my experiences thus far and I hope they will at least get the wheels turning for others who are looking to do their own thing. πŸ™‚

  4. What an inspiring read! Thank you for sharing your story! I feel I’m in the middle of a large, busy intersection not sure which road to take. I know I can always go down one and then turn around if it’s not the right one, and that there probably is no “right” one, and that’s something I need to work through.

    1. Amanda says

      Thanks for commenting, Stephanie! You are exactly right. You can always make a decision and change your mind as you learn more. That’s something I struggle with too – thinking in terms of making the “perfect” decision that’s going to suit me forever, when in fact, life is ever-evolving! Don’t put too much pressure on yourself to get it “right” the first time. <3

      1. Yes–the “perfect” decision! Oh, man! I struggle with that concept all the time. Part of being a perfectionist that has been a lifelong struggle, but one I’m working to overcome.

        Thanks. πŸ™‚

  5. Really glad you’re doing this series! Can’t wait to read more!


    1. Amanda says
  6. Emma says

    Thanks for sharing this Amanda. I’m doing a masters at the moment but will be wrapped up by September and am starting to worry about ending up stuck in a 9-5 for the rest of my life. It’s always reassuring to hear about other options working out for people.

    1. Amanda says

      I too worry about having to go back to an unfulfilling 9-5 (dreary cubicles haunt me), but I really do believe we’re capable of creating the life we want. Like I said in my post, baby steps. And leaps when the opportunities present themselves. πŸ™‚

  7. This is a very timely post. I’ve worked as a Mental Health therapist for children and adolescents for 15 years and am completely burned out. I *need* a change but financially leaving my job is very scary! I’ve got 3 kids to think about, with one in high school right now and college around the corner. I know though that the time to “leap” has to be soon. I’m hoping 2014 is my year for change.

    1. Amanda says

      You definitely have a lot on your plate, Anna. I hope 2014 will be your year for positive change too. <3

  8. Kier says

    Fabulous! You do need to be strategic when planning a big move like this, and often it is hard to keep your “eyes on the prize”. So I admire your 4 years of planning and preparing! There have been many times in my life where my husband and I have decided to save X amount of $$ so one of us could leave our job, only to fall in to old habits a few months later, with no more money in savings.

    Finally, things clicked and our dream of quitting both of our jobs to travel for a year or make big, risky, career changes, was strong enough to actually do something. We started saving every penny, put our house on the market and were prepared to hit the road as soon as possible.

    Now here I sit in January, still in my house, still in Iowa. 2014 is not shaping up how I imagined it would (was hoping to be commenting on my favorite blogs from some village in SE Asia). However – we both left our jobs (or are leaving – Friday is my last day!) to pursue other passions. And as soon as our house sells – hopefully our dream of jet-setting around the world for 365 days will be shortly realized.

    I have really enjoyed reading your posts and look forward to seeing what is to come!

    1. Amanda says

      You definitely bring up a good point with regard to planning and preparing (and saving!). It can be challenging to stay committed to the end goal when it feels like it’s in the distant future. Sorry your 2014 isn’t going as you hoped thus far, but it’s still early and it sounds like you and your husband have made great strides and will be ready when the timing is right – that in itself is worth celebrating! I hope your house sells soon, and congrats on leaving your job! xo

  9. Kait says

    Thank you so much for sharing this behind-the-scenes look with us. I feel like so many of us only see the ‘after’ and get frustrated and a little overwhelmed when trying to apply it to our own lives. Also YOU ROCK! 6 months and working from home? AMAZING. <3 <3 <3

    1. Amanda says

      Thanks, Kait. <3 I know what you mean about only showing the 'after' and that feeling out of reach. Part of my motivation for sharing the process was actually because I felt like quite a few people were under the false impression that this career change happened overnight. That's totally not the case, and also, I don't want anyone to feel like just because they can't make a big change today, doesn’t mean they can’t start making small changes to get to that big change. It takes work + discipline + patience!

      1. Kait says

        And we so appreciate it! I can think of so many of my mentors who I feel were “overnight successes” but yet none of them were. There was planning and strategy and unfortunately by the time I’m a fan, I don’t see that. Derek Halpern actually did a blog post about i this week and man screen shots of his old videos were hilarious! It totally humanizes the process and reminds us that there is work involved!

        I have a great accountability buddy this year who is pushing me to stop sitting on my hands and being overwhelmed with the big picture and start making decisions. I know I personally would love to hear more about your strategies for breaking things down and not giving into the “holy shit htere’s so much to decide and do” paralysis. πŸ™‚ xo

      2. Amanda says

        I think very few people are overnight successes, and usually when they appear to be, there was likely a lot of planning and set up to create that opportunity! That’s awesome that you have an accountability buddy. We all can benefit from that reality check from time to time. I’ll start thinking about my strategies for breaking things into more manageable pieces and see about turning that into a post. Thanks for the suggestion! xo

      3. Kait,
        My mom has volunteered to be my accountability buddy because I have the same problem of being overwhelmed by the big picture and not making any decisions. I completely know how you feel!
        I’ve found it helpful to just do one thing. Tell yourself you’ll just do one thing and you feel SO much better after and it helps you build momentum to do more. Good luck!
        Stephanie/Whole Health Dork

  10. Caitlin says

    thank you so much for posting this! i wanted to learn more about this journey. you worked your butt off for so long to get to this point and it’s incredibly inspiring. i cannot wait to read more from the series πŸ˜‰

    1. Amanda says

      I appreciate the sweet comment, Caitlin. Let me know if there’s anything related to my career change that you’d be interested in hearing more about. πŸ™‚

  11. Wendy says

    Hi Amanda,
    I just discovered your blog via I was looking for another vegan blogger in my area (I’m from Nashua) and found you, neighbor!

    This post is exactly what I needed today. I cannot shake my lack of passion for my 9-5 job in higher ed, and I have a fire in my belly right now to make a change.
    Your post resonates with me because I too am a planner, and I value the security of my income so much that I can’t just stop. Reading about your 7-month overload of contract work reminded me that I can bust my tail and prepare for my eventual change – that as scary as the change is, I can strategize and still make it happen on my terms.

    I have always connected with the blog world but fear has gotten in the way of really pushing it forward – who will actually read what I have to say (besides my mom..!), how will I ever learn photography techniques, etc but you’ve completely inspired me to go after it – because I have to, otherwise I will probably implode inside my cubicle. So I am going to get cracking on this infant-blog of mine and I have to thank you for your post since it reassured me that I can make it happen, even if it is scary, and someone only an hour away can plan and execute it, why can’t I? Thank you, you have no idea how much I needed to read this post!

    1. Amanda says

      I’m so happy you found my blog, Wendy! I know exactly how you’re feeling. I remember starting my cubicle job 4+ years ago and feeling like I would implode if I stayed there! It’s totally understandable to get overwhelmed when you’re thinking about a big career change, but as I mention in my posts, breaking things down into baby steps is what seems to work best for me and may help you too. Keep doing the things you enjoy and phasing out the things you don’t and slowly but surely you will get there!
      P.S. I’m thinking about doing a blogging series based on what I’ve learned (and I’m constantly learning), but for now – don’t worry about who will read. Put yourself and your passion into your posts and the rest will follow over time! <3


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