How I manage to travel while maintaining a demanding job

One of the most frequent questions I am asked by people I’m friends with on social media but am not close with is: Do you work? Ha. Well, yes, in fact, I do work. Actually, I work at large corporate law firm. And to put it lightly, biglaw isn’t really known for its flexibility. Despite the fact that I’m not gone as often as I seem to be and I work pretty crazy hours when I am home, I do think I manage to pull off having a bit more flexibility than the average biglaw associate.

Once people realize that I have a demanding job, they typically ask how I balance my job with travel. First let me put out a disclaimer: I know I saw this all the time, but really – I post a lot of old pictures. I usually take short trips (I just take a ton of pictures and continue to post them for long after I have gotten home). And when I’m home, I often work weekends and late nights. Having gotten that out of the way, although there is no one correct strategy to living life while maintaining a demanding job, here are a few pointers I have:

  • If you want your job to be flexible with you, be flexible with your job. The partners I work for give me a larger degree of flexibility because they know how hard I work. When we have had deadlines approaching, I have spent entire weeks working past midnight, sometimes until as late as 4am…and then showing up by 10am for the next workday. Because of this, when I ask for some time off, my partners are more flexible with me.
  • Get comfortable with last minute planning…and last minute canceling. Most demanding jobs are unpredictable, which makes planning a vacation 5 months in advance a little bit difficult. For long vacations like South America and Asia, I generally do plan months in advance and communicate my plans as soon as I make them so my bosses have plenty of time to prepare for me to be out. However, by far the vast majority of my travel is made up of shorter (generally weekend or weekend plus a day) trips. I need to be available on weekends when client work demands it, so sometimes I end up doing work from my hotel room and my vacation turns into less of a vacation. Oh well. I have gotten on a flight on a Friday, landed for a layover, read an email that I needed to be at work Saturday morning, and gotten on the next flight back home, without ever having made it to my destination. And guess what – I didn’t say a single word about it to my bosses. No matter how safe I try to be in my planning, inevitably things will come up and I will need to cancel trips. It’s unfortunate and I lose money every time, but I’ve decided that it’s worth it.
  • Shorter trips are the way to go. Do I enjoy spending 10 hours on a plane to spend 2 days on the west coast? Not really. I would much rather spend 4 or 5 days in a place that I’m flying across the country to be in. But I can’t have it all my way. I try to pack as many things as possible into very short trips. Usually I do pretty well 🙂

How I manage to travel while maintaining a demanding job

One of the most frequent questions I am asked by people I’m friends with on social media but am not close with is: Do you work? Ha. Well, yes, in fact, I do work. Actually, I work at large corporate law firm. And to put it lightly, biglaw isn’t really known for its flexibility. Despite the fact that I’m not gone as often as I seem to be and I work pretty crazy hours when I am home, I do think I manage to pull off having a bit more flexibility than the average biglaw associate.

Once people realize that I have a demanding job, they typically ask how I balance my job with travel. First let me put out a disclaimer: I know I saw this all the time, but really – I post a lot of old pictures. I usually take short trips (I just take a ton of pictures and continue to post them for long after I have gotten home). And when I’m home, I often work weekends and late nights. Having gotten that out of the way, although there is no one correct strategy to living life while maintaining a demanding job, here are a few pointers I have:

  • If you want your job to be flexible with you, be flexible with your job. The partners I work for give me a larger degree of flexibility because they know how hard I work. I am usually the first person in the office and the last person to leave the office. When we have had deadlines approaching, I have spent entire weeks working past midnight, sometimes until as late as 4am…and then showing up by 10am for the next workday. Because of this, when I ask for some time off, my partners are more flexible with me.
  • Get comfortable with last minute planning…and last minute canceling. Most demanding jobs are unpredictable, which makes planning a vacation 5 months in advance a little bit difficult. For long vacations like South America and Asia, I generally do plan months in advance and communicate my plans as soon as I make them so my bosses have plenty of time to prepare for me to be out. However, by far the vast majority of my travel is made up of shorter (generally weekend or weekend plus a day) trips. Because I work in biglaw, I need to be available on weekends when client work demands it, so I can’t just plan to be away every weekend either. Usually, I plan my vacations at the last minute. If it’s Friday, and I know I won’t need to work over the weekend, I will usually take a road trip somewhere. If I know I’ll have the weekend off a little earlier in the week, I may book a flight somewhere. Usually this works out for me, but not always. I have gotten on a flight on a Friday, landed for a layover, read an email that I needed to be at work Saturday morning, and gotten on the next flight back home, without ever having made it to my destination. And guess what – I didn’t say a single word about it to my bosses. No matter how safe I try to be in my planning, inevitably things will come up and I will need to cancel trips. It’s unfortunate and I lose money every time, but I’ve decided that it’s worth it.
  • Shorter trips are the way to go. Do I enjoy spending 10 hours on a plane to spend 2 days on the west coast? Not really. I would much rather spend 4 or 5 days in a place that I’m flying across the country to be in. But I can’t have it all my way. I try to pack as many things as possible into very short trips. Usually I do pretty well 🙂 While they certainly aren’t ideal, I’ve learned to accomplish a lot and really enjoy short trips.

Having said all of that, why do I have a demanding job? Read more about that decision in my next post.

No, I’m Not Lucky

I can’t count the number of times people have told me that I’m “lucky” to have the lifestyle I have.  I’m not.  It’s easy to write it off as “luck”, but the truths are that: (1) my life is not as glamorous as it seems (at least not always); and (2) I work really, really hard.

I’ve had this discussion with a few of my friends who are also often labeled as “lucky” – and have heard some express frustration and anger over the label.  While I personally write it off as a misunderstanding, I think it’s worth explaining a few reasons why those of us who are labeled as “lucky” by many don’t have the same view of ourselves:

  1. You could probably do it too.  No, seriously.  It’s just a matter of defining your priorities and deciding what’s important to you.  Most of us don’t go shopping for new clothes often.  We don’t spend weekends at bars ordering overpriced drinks.  We work and we travel.  Caveat: Yes, of course I realize that not everyone could do it.  But the majority of people who have told me that I’m lucky could, and this post is directed at them.
  2. We don’t talk about how lucky you are when we see pictures of you getting drunk on a Friday night.  We have decided that we enjoy other things more than weekends partying.  It’s okay that you haven’t.  But your $10 cocktails add up – and we would rather spend that money going on an adventure.  We know that we could just as well blow money at bars and clubs, but we don’t want to, and we don’t call you lucky for making that choice.
  3. We actually work really hard.  I know… it’s hard to believe that from looking at our social media.  But, need I remind you that social media can be deceiving?  The fact that I have literally thousands of pictures saved from past travels and post one a day does not mean that I’m never working.  In fact, I work all. the. time.  Not only do I work more than 40 hours a week at a law firm, but I have developed several additional sources of income that keep me busy even when I’m not at my full time job.  For example, right now I’m writing this blog post.  There are about one thousand other things I would rather be doing.  However, I know that this is what I need to do to continue to live the lifestyle I want to live.  So instead of watching other people do it and calling them lucky, I do it myself 🙂
  4. There is such a thing as posting pictures late.  I know most of us post pictures in gorgeous locations every day.  That doesn’t mean we are always there though.  Most of us take literally hundreds of pictures a day when we are traveling.  Instead of annoying everyone with hundreds of posts in one day, we post one or two and save the rest for later.  That means we have thousands of leftover pictures to choose from.  In fact, more often than not, I’m probably not at whatever location I post a picture from on a given day.  I think the same is true for a decent amount of other “lucky” people.