Saturday, May 27th, 2017

Decision Time: What Do I Do Next?


Returning home to Massachusetts has been an odd experience.

I’d forgotten that guacamole turns gray after you leave it overnight.  I’ve returned to yelling at the TV during Dancing with the Stars.   And I’m freezing.  Boston had one of its worst winters in recent memory this year, and though it’s mid-May, the trees are only beginning to bud.

Coming home has reinforced what I already knew: while I will always be a proud Bostonian, I do not want to live here long-term.  At least not at this point in my life.

My original plan was to spend the summer working at home, then move abroad during the fall — probably between September and November, and definitely before it started snowing again.  I wouldn’t make any big decisions about the location until August or so.

But I have to be realistic about one fact:

There’s a fairly decent chance that I’ll end up in a country as expensive as the US.

I need to be prepared for that.

Which means that I need to be financially self-sufficient by the fall.

Now that I’m not traveling full-time, I have the time to work on the income-generating projects I’ve been planning for months.  And there are a lot of them.  I also have time to ramp up considerably on the work I’m doing now.

I have two choices of what to do next.

Option One: Work full-time and do online work part-time.

By doing this, I’ll likely be able to save more money. I’ll be able to start the new phase of my life with a decent amount of savings, which would ease the pressure once I move.

However, I don’t think I can commit to a full-time job. I will be in Mexico with Nourish Retreats from May 28 until June 4, I have wedding activities for my friend Alexa the following week, and I have a special guest visiting me in Boston from June 26 through July 9.

The only job to which I could ethically commit would be temp work. Which I’ve done before, and which is all right, but it’s really low-paying work.  I’m not sure it would be worth putting my car back on the road or commuting to Boston by train for $9-12 per hour, then coming home and working all night.

It would give me more of a financial cushion for the fall, but I’m not sure that I would have the time to develop my new projects. And that’s what it comes down to.

Option Two: Do my online work full-time.

It will most likely mean less money in the short term. But since I’m living at home at the moment, I don’t need much, especially if I decide to keep my car off the road.

Doing my online work full-time would give me the time to develop several different business ideas, including two time-intensive writing projects. And by the late fall, I hope that at least a few could become viable income streams.

It’s a risk — a big one. But ad sales on and my other sites have been going quite well lately, and I know I can make much more than I’m making now.

I should also mention that as a Massachusetts resident, health insurance is thankfully not an issue.

There’s a lot to decide.  And I will be thinking a lot over the next few weeks.

In the meantime, there will be lots of great new material on the site. Many, many more posts on Asia, posts on my three weeks in the UK, posts on my upcoming trip to Mexico with Nourish Retreats, posts on my upcoming trips this summer.

But you’ll hear a lot about my journey into entrepreneurship as well.

No matter what happens, I assure you that there are exciting times ahead!

But for now — what do you think I should do?


50 Responses to “Decision Time: What Do I Do Next?”
  1. Stephanie says:

    Man I kind of hate you for living in Massachusetts and not having to worry about health insurance.

    I’ll be doing something along the lines of option 2 this summer, but with some more domestic travel thrown in the mix. My mom sounded kind of surprised when I told her I wouldn’t be temping or anything this summer, but I really do think my time is better spent fully committing to an online career. The one thing that does make it a bit easier for me is I still have a nice little cushion of savings. Still, it IS kind of scary too be putting all of my eggs in one basket, so I totally get where you are coming from.

    Hopefully we can inspire each other to go go go!

    • Stephanie, it’s nice to know you’re in the same position. I think that working full-time online is the best decision — if I can manage to discipline myself enough!! We could be a support system for each other!

      • Stephanie says:

        Definitely! The time management and discipline bit is by far the hardest for me. My mind starts wandering and all of a sudden I’ve killed two hours on Jezebel or something. If I’m going to make this work I’ve got to learn to focus!

  2. Shannon says:

    As someone working full time and pursuing my dream work on the nights and weekends, I’d say go with option 2 if you can. Every day I wish I had more time and energy to sink into what I hope to be making my life career out of – but it’s difficult some days to come home from a 10 hour day and put another 4-5 hours into what I really love. I do it, but it can be exhausting. I can’t help wondering if I’m holding myself back unnecessarily instead of just taking the leap. My sensible side tells me there will be a “better” time to take that leap, but if you’re already in a position to make that move, I say go for it and don’t look back. It sounds like you have a strong foundation with your ventures to build from already.

    Good luck!

    • Shannon, I’m so glad you commented — I know you’d have a good insight. That is exactly what I was doing before I left — 11-hour days, including commute, then working on my site until 2 AM. (When I moved home, my mom was horrified at my work habits.) I won’t get anything done if I go back to that.

      I did once have a boss who spent a long time saving up before quitting her job to try and make it as an artist. I’m not sure how that turned out for her, but that could be a viable option for you!

  3. Leah says:

    I am DYING to see whether or now you take the plunge into full time online work! I desperately want to do this too, and I do have a stable cushion, however, I’m TERRIFIED that if my online biz falls through that I’ll have been out of the work force too long and be unemployable!

    What’s that saying, “Fortune favors the bold?” 🙂

    • Hahaha, thanks, Leah! And I really don’t think you would be unemployable if you spent a few months working on your business, then returned to the workforce, if you listed it as your job. I think it would only matter if you worked in a rapidly changing technical industry and were completely out of the loop for a few years or so.

  4. Dan Thompson says:

    I agree with what some others have said here. I say do your online thing full time to start with and see how it works out… especially if that’s what you’re hoping to do long term(ish). Here’s the thing, you can always pick up a temp job. If it gets too hard, or the money just isn’t coming in fast enough, go get a temp job, but one thing is for certain, you’ll never know until you try it. You’re young enough that you could recover from almost anything financially (within reason of course) and you’ve got plenty of time to “start over” several times and not screw yourself later in life. I say do it.. chase your dream and see where it goes. The job market world is too easy to get sucked in to and, as you know, will start eating at your spare time to the point where it is a hassle to do your online job… or you’ll be working so much you can’t have any fun.


  5. Jeanie says:

    I’m kinda sorta in the same boat!

    I’m a terrible employee, my bank account is dwindling fast, and I don’t want to be in the position of “kept woman” even though my darling Gene has absolutely no qualms about it.

    BUT–I’m not…positioned right to “make money online” especially from ad sales and affiliate stuff.

    I’m nosing around Flexjobs for telecommuting opportunities, especially for my field of clinical social work. Considering working for the kids of military personnel. Paid travel, paycheck, and all benefits! There’s that “terrible employee” factor though…

    Fortunately, as a card carrying Native American, health/dental insurance isn’t an issue for me either. Plus–I’m mostly vegan and working toward more exercise, so I rarely get sick to begin with.

    I er, haven’t interacted with you before, but I’m a long time follower! Hope you don’t mind that I’m talking to you like we have been bff’s since diapers. 😉

    I’m interested to see what you decide.

  6. Tim Raveling says:

    Big decisions! If I were you, I’d definitely focus most of your time on your own work, building your contacts, etc. I left my stable, reliable job a couple years ago to build my own business (with the specific requirement that it could be done while on the road, anywhere in the world). It was a bit touch-and-go at first, but now it basically lets me travel as much, as long, and wherever I want. And like Dan said, if you need cash now, you could always pick up a temp job somewhere.

    Have you thought about expanding your writing income at all, by, say, writing a book? You’ve got a large enough audience you might be able to swing a deal with a publisher. If not that, online publishing is getting increasingly easy–Kindle publishing on Amazon is a snap, maybe 20 min (not including cover design and formatting), and you get 70% of the profits.

    • Tim, thanks! It’s good to know that you’ve done the same thing.

      Yes, I have two ebooks planned for release this summer, with two very different sales strategies. I’m really excited!

  7. Kate, I think it would be super tough to do some temp job around Boston for the summer. It would be low pay, no real community, and boring– talk about a 180 degree turn from where you are at right now. I am fortunate not to be in this situation, because I teach in China, which gives me a steady income. Granted I don’t spend all day traveling or exploring, but that would be too much for me anyways. I can say that working 16 hours a week is pretty awesome because it gives me a great home base, and the flexibility to write and travel (locally) a lot. So, don’t discount the possibility of finding a part time job overseas. Teaching English isn’t the only opportunity available, there are other things that could allow you to work part time– and still be able to continue all your online projects. Just something to think about. Wish you the best! I will be home to Cape Cod in middle July– really looking forward to going to the beach!

    • Tom, I’ve heard a lot of good things from you and Mike about teaching in China. You guys have a great gig!

      And I had no idea you were from the Cape! Let me know when you’re home!

  8. That certainly is a lot to think about…
    Perhaps you could do a little of both? Online and some part time work.

  9. Melvin says:

    There is a lot to decide? Really? I don’t think so! Go for the online job! 🙂

    Serious… you’ve got the stuff to do it! It’s definitely the tougher way of life, but also the better one! Go for it as long as you can and maybe get a side job to earn a few extra bucks.

    Stay patient, but I’m sure you’ll make it!

  10. Wow, as many others mentioned, I am pretty much in the exact same boat as you (and I’m even from Massachusetts!). I know exactly how you feel, I am trying to spend as much free time as I can to ramping up my side projects and finding various ways to make more side income, with the hopes of quitting my job and doing it full time. It is a really hard decision, espeically because of all the pressures from family/friends. I love Boston in September/October and early November but ugh the winter is horrible, I love the fact that I am a Bostonian too, but I can’t say I 100% see myself here forever either. Usually, I find going with your gut sometimes is the answer in these situations. I have given myself a year from now until it comes time for my own gut check, so I will be following your decision closely.

    • It’s so good to hear that from a fellow Masshole, Liz. I have NEVER enjoyed the snow. Not ever. And the fact that this place is covered with snow from at least November until March has really been taking a toll on me my whole life. I don’t want this anymore!!!

  11. Lina says:

    Work abroad!

  12. Jeremy says:

    Try to get a job on a cruise ship. You’ll save money up fast and then you can get back to pursuing blogging for a living in a matter of months. Wandering Earl can give you the inside scoop…

    • Jeremy, cruise ship jobs sound awesome, and I know Earl is the guy to ask! But for me, it’s not an option — too much of my work depends on me having regular access to good WiFi, and that’s just not a reality on cruise ships.

      • Jeremy says:

        Fair point. I think good WiFi will be demanded by people taking cruises in the very near future if not already. So good WiFi may not be a dealbreaker very soon. Oh and I vote for option 2 as well. Follow your dreams as soon as you can because the longer you wait the harder it gets to try it.

  13. Scott says:

    I am a fairly new reader to your site, I have enjoyed your stories, your vision and positive attitude. I found this post to be very interesting for me, because I feel like I am at a crossroads in my life as well, however we are at different places, I am much older and more financially secure, however my responsibilities require I work full time, as I own two companies in two different states. but I long to travel the world and do a fair amount of it, but never enough. My advice is to simply follow your passion, it may mean a combination of all your ideas. And if that doesn’t work, make no decisions until after your Yoga Retreat, after all; perhaps the answer will find you. Whatever your future holds I’m looking forward to reading about it.

    Thank you,

  14. Molee says:


    You and your “special visitor” should go to Australia or New Zealand on the Work & Holiday visa. It took them like 8 hours to approve my application and my boyfriend’s. THAT will give you plenty of stuff to write about AND you can travel and see some of the most spectacular scenery in the world. If your SV is a UK resident, it’s also super easy for him to get a WHV to work here.

    So you end up doing some backbreaking work, picking berries, up north, and then you can work at the bars down here. And the minimum wage here is about $15 for minors and more like $20 for everyone else. There’s only about 4% unemployment here too.


    • How cheeky you are, Molee. 😉

      And the working holiday visa program in Australia and New Zealand has definitely crossed my mind of late. Great tip, and I had no idea that the pay was so high and unemployment was so low!

  15. Dave says:

    Now’s the perfect time to take option 2, especially if you’ve got the support of your parents. I wouldn’t trade the freedom I have now for more money working for someone else….but I might for a new Audi. Just kidding 🙂

    I say go for it…the need to succeed will motivate you beyond belief.

  16. That sure generated a lot of comments and #2 seems to be a popular choice. I heartily concur. If you follow your passion, the money will come. Good luck!

  17. I pursued Option 2 after I got laid off. I live in uber-pricey Australia, but I make more than I ever have doing a mix of freelance writing, blogging, ghost posting and copy editing. There is no better time than now for you to do this. It will be hard work and it will take a bit to ramp up income, but if you put your mind to it, it will work out fairly quickly.

    Good luck! And if you ever want to chat about this line of work, get my email from my site home page.

  18. Sarah says:

    I agree with the whole “go abroad” movement of some of the other people commenting. Obviously I am bias, but a summer camp stint at an ESL gig in Korea is always appealing! 🙂 And they usually start around the beginning of July! You would make boatloads of cash, live rent-free (sometimes), and still get to travel. Win-win-win, right!?

    Hopefully I didn’t make your decision more difficult. But it’s definitely something to consider!

  19. Definitely go with your heart – It sounds like it will be soul destroying for you to go back toa crappy job with long hours when all you’ll want to be working on is your other projects – go for it, and give it your all, i say!

    I hope to take this plunge in about a years time, so look forward to seeing you succeed!

  20. Ben says:

    Hi, sounds like you have a big decision on your hands. If you don’t mind me asking, what types of revenue are you going for with you #2 option (obviously I’m not asking specifics to steel the ideas 🙂 , but just the type of work) ? I would love to be able to do something similar to fund my travelling.

    • Hi, Ben —

      So far, most of the income is selling ads (for lack of a better term) on my three sites. I’m working on two ebooks that I hope to finish by early August and sell with two very different sales strategies. There’s a creative project that I’m laying the groundwork for now, but promotion won’t begin until the holiday season. I’m starting new sites for affiliate programs and a new travel site. The possibilities are endless!

  21. I vote for #2 Kate! I’d LOVE to see your journey further into entrepreneurship. I know it’s easy to make more temporary money with a J.O.B., but you know you’re more cut out for working on things on your own terms, AND I think it’s a better investment to spend that time setting up your OWN income streams that have the potential to grow into more sustainable long-term assets, especially since you’ll be at home, you can take a little bit more risk right now. 😉

    • Cody, I’m really glad to hear what you have to say! Thanks so much. 🙂 You’re right, I’m in a great position for the next few months and I should take advantage of it.

  22. Katie says:

    I also have dreams/plans of starting my own business but I have a mortgage, huge amounts of student loan debt, and ongoing health care coverage is a necessaity (I don’t live in Massachusetts & I have a pre-existing condition). If it wasn’t for those 3 things, I would totally opt to just quit my full-time job and try to make a go with my business plan now.

    Since you don’t seem to have any of those issues holding you back, I say go for option #2. At least you’ll never have to wonder what if…

  23. Anthony says:

    Good luck! It’s been a blast reading and I will continue to do so.

  24. Anthony says:

    I say go for option 2 and follow your dreams! I sounds like it is the right time to do it and you have the support of your family at the moment which gives you a bit of cushioning.

  25. Claire says:

    What about waitressing? You have a great personality, so I’m sure you could make good tips, and it’s probably fairly flexible, and would give you time for planning your next adventure?

    • Claire, I’ve waitressed before and I enjoyed many aspects of it. I have thought about going back, particularly part-time, but I still don’t think they’d tolerate my schedule. 🙂

  26. I say go with option two and use the temps whenever you really need the extra. One thing for sure is there will always be people looking to hire. Once you start working a full time job its easy to get comfortable or so busy that online is not something that is really possible.

  27. Reena says:

    It sounds like you’re in a unique position to dive into the online gig full-time right now, so I would go that route if I were you. Like others have said, temp jobs will always be there (and the economy stinks right now anyway) so you don’t really have a lot to lose. Sometimes the biggest risk is to take no risk. Good luck with your decision!

  28. Alex says:

    Whatever you decide, good luck to you! You have a great cheering section here!

  29. Carla says:

    Simple. Sell your car and move ASAP. You have online work anyways, right? The longer you stay there, more things will tie you down and quiet down that little voice in your head urging you to leave. If you don’t plan to maintain a lavish lifestyle, I’m sure you could re-root yourself anywhere, quickly, without the so-called financial cushion. I can tell you from personal experience, that the financial cushion idea is, for some the responsible choice, yet for me, just a symbol that stands the fear of failure. If you lose this fear, you can be off in no time!

  30. Hi Kate, Found your blog through my daughter, Bridget Fay who lives in MA. I own an interactive marketing agency in San Diego and we’re often looking for contractors (and pay more than $8/hr). Check out our web site at and give me a call.

    I’ve enjoyed your blog very much and my business partner has also traveled the world – and often wrote about it as well.

    Cheers and welcome home!!

  31. The Hairy Chef says:

    go for #2…

    great things always come in twos…

Speak Your Mind

Tell us what you're thinking...
and oh, if you want a pic to show with your comment, go get a gravatar!

− three = zero