so you're dating your boss?

This is me at work. Riding on my boss's back. Who is also my boyfriend. Life is weird, huh?

I know I've really been off the map lately and terrible about posting, BUT it's been a bit crazy around the office the past couple weeks. (I use the term office loosely of course because my office also happens to be where I eat, sleep and vacuum up dog hair. Glamorous, ain't it?)

We've been going through some changes around the company including launching a brand spanking new website (that I helped wireframe by the way and wrote all the copy for! If you have time, feel free to enjoy some of the surprises I threw into the FAQ page!) in only two weeks and transitioning to a completely new business model. Needless to say it's been a bit hectic. Not to mention I'm redesigning this blog from the ground up (remember, it's step two of my four steps to my Etsy shop), and I've been working on it with just about every free second I have. However, I got to thinking, with all this time Jason and I have been spending on these major biz changes and all the pressure we've both been under to make it happen, maybe there's an interesting blog post in here somewhere. (Careful, I use the term interesting loosely, too.)

When I told my friends and family I was leaving my agency job at the end of last year to come on board with Jason's t-shirt wearing business, you can imagine some of them were a bit skeptical. (Actually, some of them were more than skeptical... some were convinced I was making a colossal mistake and would regret it for years to come. Yay for trying to justify my life choices to others!) I mean, I heard every logical objection under the sun.

Living together is very different than working together. I give it six weeks and you're going to get on each other's last nerve.


What if you guys break up over this? You'll be homeless AND jobless? (Okay... as accurate as that one was, that's a bit dramatic even for me!)


You'll never be able to separate work from the rest of your life. It'll consume your relationship.


What if you end up resenting him because you're not making enough money? 

You guys get the point: what if, what if, what if? In some of the favorite words of my dear friend Jason Sadler, you can 'what if' yourself to death!

I knew all the risks entering into this arrangement, but I also knew that I was willing to take those risks. I trusted that our relationship was strong enough and mature enough to adapt to this change, and in addition to that, I knew that even in the worst-case scenario I would be okay if it didn't work out. I'm confident in my skills and abilities and if it really came to it, I felt I could find another job. (Can you say Starbucks? I'd be a kick-ass barista...)

I feel like this is an important lesson in life for anyone, whether you're the one taking the risks or you're the friend trying to understand someone else's choices. In a conversation the other night with my good friend Margaret, she put it just perfectly: "I'm aware of the consequences, I'm just not fearful of the consequences," she said. Wow. It was so powerful to me. That's the key to every crazy decision I've made in my life. Each time, I've known it wasn't the safest route to go, and I've known that people were going to have their reservations, but I wasn't afraid of it not panning out because I knew I was strong enough to handle whatever might happen.

So back to the topic at hand. The truth is, it is actually working out. (Thank goodness! Homeless wouldn't be a good look for me...And honestly, now that I've really built myself up, I'm pretty confident I would not in fact be a kick-ass barista. I've been ordering the same drink for five years and I still mess up the correct order of the words.) After about eight months of doing the whole living together/working together thing, I feel that Jason and I have settled into a very healthy and happy way of operating. People ask me all the time, how do you do it? I usually toss around a few generic answers or sarcastic remarks about us laughing through it or him being a jerk of a boss, but just the other day I really started to sit and think about it. How do we do it? What lessons have we learned to make it work?

So I came up with six simple things that I think are the keys to keeping our dynamic solid. (I'm experimenting with the whole "six things" layout versus my typical unstructured and tangential rambling. We'll see how it goes.)

1. Respect each other's opinions. // Perhaps a bit obvious, but respect is HUGE for us. I didn't quit my fledgeling career in the ad agency world at two very reputable companies to put up my feet and be a glorified assistant. I have opinions - business opinions, design opinions, financial opinions - and I want to feel like I'm not only heard but that Jason trusts my instincts. From day one he has kept me in the loop and consulted me on virtually every decision. This doesn't just make me feel included, it makes me feel valued because when I take a stand on something, he takes my advice. Respect isn't just about listening, it's about truly making the other person feel that they have something to bring to the table. 

2. Pull your own weight. // The whole working together happily thing falls apart unless you wake up every day intent on being an asset to the company. This is especially true when the company is super small because every bit of effort counts. I may have made risks to take this job, but I'm mindful of the fact that Jason took a big risk too. I know just how hard he works for every dollar brought into the company, and just like any other part of the team, when I get paid I want to know that I earned it. So I choose to approach it like any other job - by being proactive, being valuable, being indispensable. I do that, feel no guilt on payday because I deserve every last cent, and Jason doesn't come to resent me for carrying dead weight on the company's back. (Hint: guilt and resentment are kind of killjoys in a relationship.) It may sound a bit extreme (and maybe that's just my commitment to the company showing through) but he works hard and so I know that to keep things in balance I have to work hard too. (Hard work of course is an easier pill to swallow when you love the company you work for.)

3. Make time to walk away. // Not only do Jason and I work in the same office, but that office is also our home. I'd be lying if I said it was easy to keep clearly defined boundaries. It's not at all. Although we have an office, it's not unlike us to be sitting on the couch with our laptops in front of us, continuing to work long after "the work day" is over. I mean, when you're dating the boss, there's nowhere to hide. It's not like I can pretend I didn't see an email come through until the next morning. With all this blurring of work and leisure, that's why we both know it's important to take time to walk away together. We'll take breaks to take Plax for a walk, or work out, make dinner, watch a movie, etc. And during that time we do our best to turn down the volume on work. (Notice I didn't say turn it off. If you know any entrepreneurs, it doesn't get turned off. It's impossible. But we try our darndest.) Work may creep into the conversation, and that's okay. As long as we're laughing and spending quality time together, it works.

4. Define the roles up front. // (This little section is probably going to end up sounding a little anti-feminist, but what the hey. It is what it is.) Part of making it work is knowing who the boss is. Before I started, I asked Jason for a list of responsibilities that I would be responsible for. Along the way that list has changed dramatically, but periodically I stop to ask so that I know where the boundaries lie. I take care of my territory, and he doesn't micromanage (which is an integral part to keeping my sanity.) As I mentioned, he asks for my input on nearly everything, but at the end of the day, he's the boss. And I totally respect that. He is the one that built this business from nothing, not me. And while I may have its best interest at heart, we could go round after round on decisions if we wanted to. Which is why it's much more efficient when there is one person steering the ship. Knowing this and respecting this up front diffuses a lot of arguments. It also makes me feel more purposeful and fulfilled in my own work because I know exactly  what I'm in charge of.

5. Show appreciation. // You know when you work really hard on something and you feel super proud of the way it turned out and you get NO acknowledgement from your boss or manager? And you know when you work really hard on your relationship and you focus all your energy on all the areas you feel you've been lacking in the past and get NO acknowledgement from your significant other? Yeah... stack those two emotions on top of each other and it's enough to make a girl run for the hills. That's why appreciation is so important. Saying thank you and recognizing each other's work is even more important than it is in a typical work environment because feeling under-appreciated has the potential to seep into the relationship. A little acknowledgement goes a long way.

6. Let things go. // This is one that definitely took a bit longer for me to adopt than the others, but it might be most important of all. There are always going to be arguments and disagreements. I'll be having a bad day sometimes, or he'll be having a bad day. Sometimes I don't feel like brainstorming, and sometimes he doesn't feel like listening to all my nit-picky design changes. So when things get heated, I take a step back, breathe deeply, and remember that I have the unbelievably rare pleasure of building a company with my best friend. That gratitude is enough to make me drop whatever momentary grudge I may have.

And there you have it. For all inquiries from this day forward, maybe I'll just direct interested parties to this blog post. But really I think this one was for me. I'm proud of everything we've been through thus far in our professional relationship, and I'm proud of how we've kept our personal relationship in tact. More than anything it's so reassuring to know that the gut feeling I had when I started this thing was right. If anybody could make it work, I knew it was us. Looking forward to the future of IWearYourShirt, and I'm honored and inspired to be a part of such a great team.

And to have such a hot boss. That doesn't hurt either.