Wednesday, November 19, 2014

Ask Cloud: Have Kids, Will Travel, Want Career

A long time reader has sent me a question for my occasional Ask Cloud series. Here is the question, edited lightly to preserve anonymity:


I've been following your blog since grad school (7+ years) and have really enjoyed seeing into the future as I'm probably 5 years behind you kids and career-wise. I'm struggling with what to do next and since your career has taken a few twists and turns, I'm wondering if you have any insights.

Short summary is that I have a life science PhD and have been working at a small company in a related field for 6 years.  It's great for flexibility as I've built up my career capital there but not so much for career (or salary) development. 

I am currently on a maternity leave and the odds are 50/50 whether my company will exist a year from now.  This has let me dream about the future a bit - my husband and I have decided we want to make travel with our kids a priority and have started on a 5 year plan. We realize taking a full year off could be difficult career wise, but working remotely is definitely a possibility. We'll be traveling a lot this year so we know we'll learn a lot from this experience!

I'm in a long scanner phase trying to figure out where the next career move is - do I: 

1. move to a bigger company, develop my career more and salary more? 
2. go back to my company (if it exists) as the flex work opportunities would be high
3. Work towards a travel friendly career (I was taking some programming courses before pregnancy brain made it too difficult. I've decided to start a blog/twitter travel account and experiment with social media this year (@raisingtravelrs). I've considered a teaching English to adults certification, and I've picked up crocheting, which maybe could support a small business if we lived in a low-cost country, who knows!)

As you can see I don't need traditional resume help, I'm more focused on how I want my resume to look in 5 years.


First of all, wow! Someone who has been reading my blog for 7+ years has essentially been reading from the start. I am truly honored to have someone who has stuck with me that long.

Now, on to an attempt to answer your question.

There is a lot to think about in there. I can certainly sympathize with wanting a career that is more conducive to a travel-heavy lifestyle. That is in fact one of the things that pushed me to make a change in my own career.

I'll give you my thoughts on your options one ant a time:

Option 1: Move to a bigger company

There can be a surprising amount of flexibility in a big company, but I think a lot depends on your boss and how invested he/she is in having you stay. I think this is true even in companies that have great flex work policies- the culture of your particular team will determine whether or not using those policies will be possible without stalling your career.

My gut instinct on this option is that you'd need a couple of years of standard work hours to build up the credibility and track record that would make an average boss willing to stick his or her neck out for you and fight for the flexibility that you really want. You could get lucky and get a better than average boss, or land in a better than average corporate culture- but that is very hard to suss out ahead of time, so my opinion is that if you go with this option, you should be mentally prepared for it to be a couple of years before you can really get much flexibility

However, the better money is definitely something to consider. My current work arrangement was made possible by the large buffer of savings we'd built up. Money really can buy career freedom, and it might make sense to have a long term strategy that includes time spent just accumulating money.

Option 2: Return to your current company

This is certainly an appealing option, since you've already got the credibility there to get the flexibility you want. I'd think about a couple of things when considering this option: the extent to which your lack of career growth will bother you and whether the uncertainty about the company continuing to exist would hinder you in taking some of the "big" flexibility you want. There is no right answer to either of those questions- it is a matter of knowing how you (and your husband) react to different types of risk.

Option 3: Change to a more travel friendly career

I think this is the hardest option on your list- even though it is the option I've decided to go with myself. Sure, coding and writing (for instance) are both careers that can be quite travel friendly, but getting to the point where you can actually make that work is tough.

Most of the coders I know who manage this are quite experienced. This helps both because they are great developers (practice improves performance, for sure!) and because they have a deep network of potential clients. Their high hourly rate and large network make it easier for them to turn work down when it doesn't suit them, secure in the knowledge that they'll be able to survive until the next job becomes available.

Writing as a full time career option is tough for different reasons, mostly around the fact that the supply side of that market is quite full. I fantasized about quitting my job and becoming a full time writer for quite awhile, and then I came across an old post of John Scalzi's in which he laid out some details about his finances. At this point, he was a NY Times bestselling author with a solid collection of books, and he was still making roughly what I was as a middle manager. Now, neither of us were hurting for money (and I'm almost certain he now makes far more money than I do, given how his career has taken off) but it gave me a shot of realism, which changed how I thought about that career option.

Now, I don't want to say you wouldn't succeed in either of those careers! Obviously, people do. I am just explaining why I consider this such a difficult option.

Towards the end of your description of this option is a potential way to mitigate this risk, though- which you could actually use to mitigate the risks in any of the options. I'll call it option 4.

Option 4: Build multiple income streams

There is no natural law of the universe that says you have to have a single career. There is a lot of advice out there claiming that you HAVE to focus on one and only one thing to be successful, but I think that is not universally true. Some people really do best when they focus, but others do better when they have multiple things going at once, some folks like to do different things in succession. It might help to read (or re-read?) one of the books I referenced in my old post about being a "scanner" with special focus on figuring out what approach seems most natural to you.

Also, consider that you have skills that you've already built up over the years that you can use to contribute an income stream. You mention crocheting, for instance.

I think the key to using this option is to be clear about how much money you're likely to garner from each stream, and to pick realistic projects given your skill level. For instance, I have an idea for some apps that I think could do pretty well. But I don't have anywhere near the skill level required to write those apps. In fact, I don't even feel like I could do a good job specifying the apps right now. So, instead of jumping straight in on those apps, I have a couple of easier projects to do first, to help me build the skills I'd need to tackle the more complicated apps. (And I have other income streams that can keep me fed in the meantime.)

Once you start thinking about income streams, you can get quite creative in building a work life that will really work for you. For instance- my recent decision to become a publisher wouldn't have occurred to me before I switched to an "income stream" mindset. In this mindset, I don't have to make heaps of money as a publisher. I just have to do well enough to make it worth my time (and to convince authors to publish with me). Only time will tell whether or not this approach works for me, but I am loving this new mindset right now. It is helping me take risks that I wouldn't have had the courage to take when I was in my "build a single career" mindset.

That brings me to my final thoughts on this. I think one of the hardest things about making this sort of change is that regardless of which option you take, you're stepping off the usual path. A lot of people will express incredulity at your plans. You'll probably have an internal critic that expresses incredulity at your plans! Also, like most changes, it will take time to execute. You can be executing your five year plan flawlessly and still look a bit scattered or lost in year two, and people won't necessarily keep their opinion on that to themselves. So, if you do this, you have to have some method for keeping your final goal in sight, and you need to develop a way to get a realistic (i.e., not overly pessimistic OR overly optimistic) gauge of your progress.  I'm still working on that part, but I'm far enough into my own career change to know that these things will be important for my long term success.

That's all I have. Any readers want to weigh in with ideas and/or advice?


  1. If your programming job can be done 100% remotely, then it will be done in India. Don't bother training for a job that doesn't exist.

    Coding, and finding and fixing bugs, takes concentration. Can you really do it while traveling and w/o consistent daycare and schooling for your children? Be realistic.

    1. The programmers I know who combine work and travel mostly do it in a work-travel-work-travel pattern- i.e., they do project work, and turn down projects when they want to be traveling.

      I also know some IT consultants who pick up freelance work while they're traveling. I think they use local day care, though- they tend to stay in one place for several months at a time.

  2. I'm a lot more optimistic about writing as a career than many people are, but it is a career like anything else, meaning that to earn a good living just from writing, you really have to build up your experience and connections. However, it is a good supplement to a lot of other things as a secondary income stream. So your reader is doing the right thing by starting a blog to figure out what she can write about that might attract an audience, to start building a platform, and to get practice at the craft. And hey, if she's been reading here for 7 years then she's been getting a good sense of what works!

    1. It is good you're optimistic about writing as a career! I think it is highly unlikely I could ever be successful enough in it to have it be my main source of income- but then, I am not taking the time to build networks in the writing world and really focus on improving as a writer. That is all subject to change, of course! I'm enjoying writing as a second income stream, and maybe someday I'll decide to focus on it more.

  3. FIrst, thanks for the in-depth analysis, it's really helpful to hear someone else's thought process on this. I find my typical social circle can't get past the various barriers they see (kids are too young, risk in changing jobs, risk in moving, etc).

    Your final thoughts are bang on - my inner critic was raving this week, particularly as we were trying to plan a month-long stay in NYC, in the winter, with a 3mo and 3.5yo (any combo of those things seems to strike fear in many people!) I'm still working through better ways to get through those moments, but they may just be part of the process of being more comfortable with risk and change.

    I'm not sure yet how to track progress, right now it's the little things, like being away from home for a month and having the 3.5yo thrive in the new adventures.

    I have some buffer before I have to decide on the job front, but I am slowly working towards option 4 by experimenting with a few different things to see what might stick. I'm hoping my website will give me both writing and tech experience as I tinker under the hood with the HTML/CSS and write-up my traveling with kids posts.


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