four things i learned from being the boss for a year

February 12th, 2015


Many of you may remember that a little over a year ago, I left my job at a law firm to start my own legal practice. I was at a crossroads in my career, and I knew that if I ever wanted to make this jump, this was my window.

And oh my gosh: what a year it’s been.

{Actually, it’s been almost a year and a half at this point, but it took me about six months to have enough spare time to draft this post, ha.  Such is life.}

It’s been really, really amazing. And also really, really hard.

Sure, having a baby added a whole new set of complications (I touched on them a little bit when I wrote about being a working mom). But many of the challenges that I’ve worked through in the last year have nothing to do with being a mom, and everything to do with starting a business.

So I thought that I’d put together some small pieces of advice that I’ve gathered throughout the past year. Starting a business takes full commitment, all the hours you can devote to it, and a ton of creativity and energy. It takes flexibility, determination, and an incredible amount of grunt work.

And once you’re done with that, here are a few more things to keep on your mind.

Delegate Everything You Can.

My first day working at a huge law firm in Manhattan, we learned: When you can delegate, you should. I was 25 at the time, and honestly, I felt nervous and awkward at the idea that I was qualified to assign tasks to anyone (even my secretary, who at that point had more years of experience in the legal industry than I did).

But my firm made clear: this was the first and most crucial skill that I was expected to learn. A client would not put up with me spending two hours drafting mailing labels because I thought it was awkward to ask my assistant to do it. I was expected to take advantage of their resources, so that I could do what they paid me for: being a lawyer.

In retrospect, it was the best lesson I could have learned. Like many of us who are perfectionists, I have a tendency to micro-manage projects, and I worry that no one else is going to do every task as well as I can. But… that tendency sucks up a ton of time that’s better spent elsewhere.

Your time is valuable. Spend it challenging yourself, learning new skills, and pushing your brain to its limits. And when you can get help, do it. So delegate whatever you can, and focus your time accordingly.

Stop Worrying.

Ok, truthfully?

This one took me a long time to learn.

My first year in business, I worried a lot.  I worried when I quit my stable, high-paying job, I worried during my first few months as I waited for the phone to ring, and I sometimes still worry. There are so many worries for your mind to fixate on: What if I lose this case? What if I don’t get this client? What if my phone stops ringing?

But, you know what? All of those things are out of my control. They always were. Worrying is never going to make the phone ring, and it’s never going to change whether you succeed. It’s going to make you miserable, and distract you from taking chances that might just pay out in the long run.

So I’ve started to let go of my worries, and embrace the flexibility and creativity that get stifled when you spend every minute worrying about things in the future.  Right now, what I’m doing is working.  And focusing on that is more productive than all the worst- and best-case scenarios I can think of.

Build a Network.

Success isn’t just a measure of how hard you work; the relationships you build are equally important. I’ve been lucky throughout my career to work with incredible mentors and colleagues, many of whom I still regularly call on for advice. Especially when I first started my practice, my network of seasoned, experienced lawyers answered my questions, vetted my ideas, and provided me with countless hours of knowledge and advice.

And here’s the great thing about being a woman: we are natural networkers. We’re comfortable talking. We keep in touch. We maintain larger social networks, and we bond incredibly closely with our friends. This is one aspect of business that’s sitting there, waiting for us: all we have to do is reach for it.

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When the Going Gets Tough… Just Keep Going.

The biggest thing I worried about during my first year in business? The topic of all those sleepless nights?


I worried that I’d spend a year, or five years, or ten years, doing this, and I wouldn’t be able to make it succeed. That my sheer force of will wouldn’t be strong enough.  I worried that no matter what I did, some element of success was out of my control.

Some days that failure felt imminent. When I didn’t get a case that I really wanted. When I was up at midnight because the baby hadn’t slept and I had a brief to finish. When I had to take a deep breath because my to-do list was a mile long and I was still on the first item.

In short: When any obstacle got thrown in my path, that fear re-emerged.

But it’s been a year, and I haven’t failed. Sure, there’s some relief there. But there’s also something even more valuable: I’ve come to terms with the fact that that even if I did, or if I still do, failure isn’t the end of the world.

So here’s what I say to someone who’s in the position I was in a year ago, worried about the uncertainty but itching to try anyway:

Life is long and you’ll have many chances to do many things. Maybe this one will work out — hopefully, it will. But if it doesn’t? You’ll pick up the pieces and move forward.

You will be wiser for the experience, even if it’s painful.  Failure can teach you lessons that you’ll never learn from success. That, in itself, has value.

One of my favorite pieces of inspiration is a speech that Steve Jobs gave for Stanford Commencement in 2005. I’ve probably read it a hundred times, particularly in moments of doubt and uncertainty.

His last few words are hanging on a print in my home office: Stay Hungry. Stay Foolish.

My first year in business was hungry and foolish. It was scary and exhilarating and maddening and stressful beyond belief, and it was also one of the things that I will be proud of doing for the rest of my life. It was jumping off a cliff to see if I could fly, and it was unlike any experience I’ve ever had.

It has profoundly changed the way I think about my career, in ways that will be with me for the rest of my life. It has given me responsibility, discipline, and drive that I couldn’t have imagined a year ago.

For every sleepless night, there was another full of exhilaration, full of celebration, and full of tiny little victories that kept me going, day after day.

I learned a thousand lessons — sometimes that were exciting, some that were painful.

I learned when to trust my gut and when to trust my experience… and when to just flip a coin and call it a day.

I learned that, at the end of your first year, the process of making these decisions is just getting started.

I learned that every day brings some new challenge that I am stronger and better for having overcome.

For a girl whose life has been spent on a pretty rigid trajectory, I learned the freedom of inventing a path for yourself, and the flexibility and grit that it requires.

And, you know what? I’m still learning, every single day.

So ask me again at the end of Year Two.


Tags: work

4 responses so far ↓

  • 1 Laura // Feb 13, 2015 at 12:33 am

    Slightly off topic from this post (I apologize) but do you have any recommendations for stylish, reasonable bags big enough to fit legal files and a laptop? Thanks!

  • 2 Katy // Feb 13, 2015 at 12:17 pm

    I use my Brahmin bags all the time!  I’m not sure about the laptop (I usually use my iPad with a bluetooth keyboard for travel) but they definitely fit redwelds with files.  Before that, I had a Longchamp bag that was also great!  I should do a post on this, actually!

  • 3 Emily // Feb 13, 2015 at 7:45 pm

    Thanks so much for this great post! I’m a new mom to an eight month old boy and lawyer too.  Sometimes I feel really overwhelmed but reading about other working moms makes me feel better.  I know other moms make it work so I can too. So thanks again!

  • 4 Jack // Dec 28, 2017 at 6:02 am

    All discounted products and much more at

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