I'll be Working on Vacation – What's Your Idea of Work/Life Balance?

My father turned 60 last month. The plan was always to bring him to Ireland for his 60th birthday. Unfortunately, the recession hit and I'm a little short on cash, so we're scrapping the plan until his 61st, and going on a short family vacation to West Palm Beach.

It's been a long time since I went on a real vacation. Since starting Brazen Careerist, I haven't really taken any time off. Work is always on my mind, and I've found some way to work every single day for the past 18 months. In a lot of ways it doesn't seem right to drop everything and take a real vacation. We just took in some funding, we're gaining new users and readers faster than ever, and I'm full of ideas for where the site should go in the next six to twelve months. The truth is, shutting off for four days doesn't even sound like fun.

So, Ive decided that I will be working on vacation. I won't be sitting in front of a computer all day, but I will be running new ideas past my brother and Rebecca. I'll be discussing our latest financing round and other issues with my parents. And I'll probably put together a PowerPoint presentation for our March board meeting on the plane and at the airports.

I have allowed work to completely, totally, consume my life, and I couldn't be happier. After years of discussing what work life balance really means I've realized that to me, at this point in time, working on vacation is my perfect work/life balance.

What's yours?

For more thoughts on working on vacation, check out the post I wrote from Napa Valley, California (my last real vacation)

When Working on Vacation Isn't Really Work

I'll be Working on Vacation – What's Your Idea of Work/Life Balance?

My father turned 60 last month. The plan was always to bring him to Ireland for his 60th birthday. Unfortunately, the recession hit and I'm a little short on cash, so we're scrapping the plan until his 61st, and going on a short family vacation to West Palm Beach.

It's been a long time since I went on a real vacation. Since starting Brazen Careerist, I haven't really taken any time off. Work is always on my mind, and I've found some way to work every single day for the past 18 months. In a lot of ways it doesn't seem right to drop everything and take a real vacation. We just took in some funding, we're gaining new users and readers faster than ever, and I'm full of ideas for where the site should go in the next six to twelve months. The truth is, shutting off for four days doesn't even sound like fun.

So, Ive decided that I will be working on vacation. I won't be sitting in front of a computer all day, but I will be running new ideas past my brother and Rebecca. I'll be discussing our latest financing round and other issues with my parents. And I'll probably put together a PowerPoint presentation for our March board meeting on the plane and at the airports.

I have allowed work to completely, totally, consume my life, and I couldn't be happier. After years of discussing what work life balance really means I've realized that to me, at this point in time, working on vacation is my perfect work/life balance.

What's yours?

For more thoughts on working on vacation, check out the post I wrote from Napa Valley, California (my last real vacation)

When Working on Vacation Isn't Really Work

A Bad Economy Is the Perfect Time to Start Over

My first six months in Wisconsin were interesting to say the least. Ryan Paugh and I lived on $1,000 a month in a beat up old house on the East Side of Madison. We worked from home, we rarely went out, we fought with each other, we fought with Penelope, and we watched the snow pile up on the cold Wisconsin ground month after month.

By all accounts, it was pretty terrible. I was used to having lots of friends, going out all the time, and counting on a good paycheck to come in every other week.

But then we raised some money. We took bonuses, we got regular paychecks, we hired people, we rented an office, and I moved in to a nice place with my brother and bought a flat screen TV. It was great. It was comfortable.

It was boring.

Any true entrepreneur will tell you that the best time in the life of a start up is the beginning. You work tons of hours and you can't wait until you're funded because that's when you'll be able to do the things you really want to do.

But once you get funded, the headaches just begin, and it starts to feel like a "real job." It's easy to get comfortable, to forget about all the hard work you put in before there was cash in the bank. And strangely enough, you end up wishing you could go back to the beginning or sell your company and start a new one.

Rather than being completely focused on the company, I found myself walking down the street, sometimes nostalgic about the little apartment Ryan and I lived in and sometimes dreaming about our big exit and all the money that would come with it.

Then, before we even realized what was happening, the market crashed, investors pulled back, and we didn't have salaries anymore. The whole company had gotten too comfortable; we weren't prepared to handle the downturn.

But oddly enough, three months later, things are going really well. We made a decision to switch up our business model and bring in revenue any way possible. Every dollar we make is treated like gold, we've managed to cut our burn rate by nearly 50% without losing any productivity, and we've realized just how many ways there are to make money, without begging someone for a multimillion dollar investment

I'm confident that we're going to make it through, and I'm convinced that when Brazen Careerist does end up a success, we will have George Bush to thank (Did I really say that?). The recession allowed us, or some might say forced us, to reevaluate and start over.

In a way, I did get my wish, Brazen is like a brand new start up, except we have a site that's already built, we have founders who have all done this part before, and we have a whole army of people that want us to succeed.

I've learned a lot from this whole experience, both personally and professionally. Difficult situations are the best learning opportunities; when things are good it's very difficult to see how you can improve. But when times are tough you have the opportunity to make difficult, life-altering decisions. Great businesses and great leaders embrace difficult situations and thrive when times are tough.

The question is, when adversity is staring you in the face, will you get comfortable, or will you embrace the adversity and emerge stronger than ever?

Generation Y: Here Are the Real Dues We Need to Pay

When I hear older generations talk about Generation Y having to pay their dues, I get a little sick to my stomach. Not because I'm trying so hard to avoid the whole thing (I am), but because I have more important things to develop before worrying about a fat paycheck and a corner office with a view.

Due paying gets a bad rap because it's consistently associated with cubicles, meaningless work and low-paying jobs with little benefit. But I believe that there are other inevitable obstacles—more important ones—that we need to conquer before deciding where we stand within the working world.

Here are three due-paying opportunities that we all need to think about before fussing over the traditional connotation of "paying your dues."

Discover who your true friends are.

If you're more than a year out of college you've likely figured it out—everyone you considered friends at school is not going to be there forever. In fact, it's quite possible that you'll encounter some mild betrayal before long. It comes with the territory.

I consider myself pretty lucky. But there are times when I'm utterly let down. And because everyone has their own goals, though sometimes fairly hazy goals, you shouldn't dwell on the people in your life that didn't end up being as loyal as you thought they would be.

What I've learned to do is this: whenever somebody lets you down, put your energy into someone who consistently picks you up. Those are the people you want to center your life around. And it's those people who will continue to add meaning in your life as you pay your dues as a twentysomething.

Discover what it's like to be alone.

While I continue to realize that I still have some true friends, there are still days when I can't help but feel lost and alone. And I think that most people feel this way at some point.

Whether you're single, dating or married, we all have to figure out for ourselves where we fit in the world. Sure, you can count on your loved ones for support, but it's you alone who makes the decision about where you fit and what makes you happy.

One thing I've learned since moving to Madison and starting Brazen Careerist is that life can't be measured by your social life alone, and it's certainly not measured by a paycheck or by where you stand in the hierarchy of the working world. The most important measure in life is how you feel about yourself. And some of the biggest revelations will hit you not when you're out partying with friends or working towards a higher salary, but when you're by yourself, alone and kind of unsettled by the things that are still missing in your life.

Sound depressing? Sure. It's seldom a fairy tale experience for any of us. But what you learn through these experiences is what you need to move forward and be more of the person you want to be someday.

Feeling alone is a big part of paying your dues. Don't fear it; try to embrace it and get comfortable.

Discover your fear, and conquer it.

Lately I've been reading Christine Hassler's 20 Something Manifesto. I learn best from listening to other people's experiences and this book is jammed-pack with twenty-something life.

Today I read about fear and I can't stop thinking about what Christine says:

If you have a skill, dream, or desire that you are passionate about pursuing, perhaps the biggest obstacle you will face is your own fear…Fear can keep us in bad situations, and also from pursuing our passions. Fear can often be a stronger motivator than the desire for success, stopping us in our tracks before we even find out what we want.

Lately I've been talking to a few people who seem to have something in mind that they want to do, but aren't sure how to really do it. But I'm starting to believe it's less about the actual drawing out a plan and more about drawing up the courage to make it happen.

Whether it's leaving a new job, starting a new one, moving away from family and friends, or any other daunting scenario I've ever faced, the most difficult part of the transition was mustering up the courage to do it. But once I sucked things up and overcame the fear of failure, everything else was gravy in comparison.

And sure, I still encounter little failures along the way. But they only make me better. A few scars are worth the irritation because you'll look at them later and remember what you did wrong that put them there in the first place.

So before you fret about office politics or the way the working world views Generation Y, think about developing yourself. People are always going to whine about how lazy and self-absorbed young people are, so let's just spend these years paying real dues first–ones that will actually pay off for the rest of our lives.

What to Do When You Hit a Juncture: Don't Put Life on Hold

One of the most important things I've learned over the past year is that you should aim to live in a place that mirrors your own personality. Unfortunately, most of us won't find ourselves in that perfect place from the get-go. So it's important to not let it get you down, or keep you from achieving your goals.

I have no intention of staying in Madison for more than a couple years. Just enough time to get our business going and hopefully move somewhere that suits my personality. But a couple years is a long time. If I just put things off because I'm waiting for the perfect place to take action, I'll miss out on a lot I've looked forward to for years. Timing isn't always everything. The other half is putting your dreams into action.

What I realized through my lack of action over the past year is that great things can happen in a juncture. We're really just procrastinating when we deceive ourselves into thinking we should wait.

Have you ever told yourself these things in a juncture?

If I'm just patient, good things will happen to me.

Image Credit: jenvanw
The first time I probably told myself this was in high school. And it was probably over a girl. Because I was probably awkward and goofy.

But with confidence and a few more years under the belt, we should all learn that patience is only half a virtue. The second half is a willingness to put yourself out there, even if it might crush your ego.

If you're in a new city and you're social life sucks, it's probably because you're not taking enough risks. Being quiet and reserved can seem like the right move because it's safe, but in fact, it's killing your chances of meeting the right people.

Weekend homework assignment: Go to the bar and put yourself in a situation that runs the risk of making an ass out of you in front of the opposite of sex. Sound like an all-time backfire? Maybe.

But maybe not. Great relationships usually begin during awkward moments. Test the theory out for yourself. If you fail, miserably, I'll owe you a drink.

I should just put in more hours working. I'll enjoy myself later.

When we first came to Madison we lived via late-night meetings, skipping out on happy hours – it was a first-class ticket to depression.

And I really hate that I used to live like that. There's a risk of having only weak relationships when you choose to live this way. Fall into this trap now, and who's to say you'll escape from it later?

My new approach: go out whenever you can reasonably afford to. As long as it doesn't seriously affect your work, it's as an important element on your path to success as climbing that ladder every day.

Everything I create here won't matter once I leave. Why waste my time?

I once met a girl from Mexico who convinced me to study Spanish. I went home and bought Rosetta Stone. Granted, I'm susceptible to foreign girls, but it's proof enough to me that short-term friendships can affect our lives.

Now that I'm finally settled in Madison, I'm embracing every new friendship I possibly can because I've learned to be okay with "temporary." Change is going to happen and nothing is permanent.

People who can adapt quickly to change can find happiness almost anywhere. So learn to embrace where you are all the time, even if deep down you wonder if you will ever think anything but "this sucks."

It's doubtful that anyone in their twenties is completely in tune with their environment. And even if you are, that will probably change as you grow older. What's important to realize is, as long as you're willing to embrace where you are today, you're probably going to end up in the right place tomorrow.