How Failing Led Me To My Greatest Success

What if I fail?

It’s a question that I’ve asked myself often. I’m going to guess you have too.

Back when I was in my 20s, I was careful to only take on challenges that I was pretty sure I couldn’t fail at. I would dip my toe in, test out my skills in whatever I was thinking about tackling, and if I decided my chances of success weren’t great enough, I’d move along and focus on something I knew I could crush.

But on this day, 6 years ago, I was on my way to visit my best friend Shannon and I found out I was pregnant. Well, I didn’t just find out…I thought something was up and I took a pregnancy test. When I saw the results, the room went silent, time stood still and I felt like I was drowning. 

I felt like my life was over. O.V.E.R. I cried so hard while sitting in Shannon’s Hermosa Beach apartment that it still makes my stomach flip when I think about it. I was consumed with the fear of failure. Consumed. Paralyzed by it. 

There was no dipping my toe into single working motherhood…no, no, I was thrown into accepting that reality and I was terrified. 

When I was about 4 months pregnant I couldn’t keep my fear of failure to myself, and I really came undone. So I called my on-again, off-again ex, Jim. Which may seem like an interesting person to reach out to, but it made sense at the time. And all these years later I am glad I did.

Our conversation went a little something like this:

“Hey … it’s me … are you busy?” I asked him, expecting him to say, “Yes.”

“Nope,” he said.

“Are you alone?” I asked, hoping the answer was yes.  

“Yep. Are you alone?”

“Not funny Jim, I am starting to freak out. I heard the baby’s heartbeat today…”

“I know, you emailed me. You know that baby looks like it already has big cheeks, right?” he inserted.

“Yes, I noticed that. But what I am really having a hard time with right now is my life. It is not in any condition to have a baby. I mean I want this baby, but I just don’t know how I am going to get from here to there. And what if I fail and f*ck this child up? Then what? …”

And then the tears came. They flowed with force. And once I started down the path, I couldn’t stop…unravelling about obstacles big and small, perceived and real.  

“I am so scared. And even though in my core I know that everything will be OK, I don’t know HOW and it scares the shit out of me. I don’t know how I am ever going to go to the gym again, or get a haircut or do my laundry at the Laundromat two blocks away. And I am so mad that it hurts. And everyone is so worried about me that I feel smothered, and on the other hand I feel completely alone. I don’t have an example of how to do this. There will be no one there with me at 1 a.m. when the baby won’t stop crying. There is no one to tell me that I am not going to f*ck this up royally. And on top of it, I work in one of the most demanding industries and I go to work at 3:30 a.m. And everyone keeps telling me what a great mom I’ll be and how everything will be fine and for some reason I find it infuriating. ”

I heard Jim open a beer. And take a deep breath. And then he began to speak.

“My mom got haircuts all the time and never when Dad was watching us, so there has to be some way to get that done. You have figured everything out so far in this city, and haven’t failed yet. So why do you think you will fail with this? Yes, your life will change and your friendships with be redefined, but that isn’t such a bad thing. You and the baby are a team. And yes, there will be things that you can’t do, but an entirely new world will be opened up to you.”

I wiped my eyes and took a deep breath. We continued talking for a while longer, and somewhere in there I took one tiny, small, infinitesimal step forward.

“You really believe everything you just said?” I asked, wanting more than anything else, an ice-cold beer.

“Yep. I do.”

“Thank you. You did make me feel better.”

“I know I did. Listen…Just try focusing on the next 7 months instead of the next 7 years,” and then he laughed, “I just realized how neurotic moms become neurotic moms. In front of you, you have all these months of testing and doctor’s appointment and people telling you all the things that can go wrong, and you go from a normal carefree girl that I used to get wasted with, to a mom. It’s actually quite amazing. And you are already doing a great job.”

I look back at then and now.

And in some ways, I totally did fail. I am no longer in New York City, I no longer work in news, and my life looks NOTHING like it did before. The house, the suburbs, the working from home, the car, all of this was not in my plans. So yes, I failed at maintaining my old life. I tried to hold on as long as I could … and then, one July afternoon, I decided it was time to stop holding on to the old image of my life and to really accept what was a much more manageable life for Ellie and me.

And while I failed at maintaining the old life, what I gained when that fell away was something pretty incredible. An even closer relationship with my sisters, an ability to see my parents whenever we want, a reconnection with high school friends who have known me for more than half my life, a new and challenging career path, new co-workers that I really enjoy, a lack of shared walls and downstairs neighbors who hate the sound my boots make when they hit the floor, and a chance to sort of write the script of my life as I go.

Accepting this is not all easy. There are some days I miss my old life so much that I can’t help but cry. In fact, I did just that a couple weeks ago. But thankfully those days are few and far between and I chalk them up to the fact that making peace with missing my old life is a process…one that may never actually be done.

I keep that boarding pass from 6 years ago in my office so that I have a constant reminder that both my life and my ideas about failure have changed.

On that day and in that phone call a few months later, I was measuring my failure and success by the terms of my old life. And if I look at my reality through that lens, then yes, I did fail. But, and it’s a big but here, if I open my eyes and take in the big picture, I see I am succeeding at a life that I am very much in love with.

It’s not like I have all the answers, I still worry about a laundry list of things…um…all the time. But I’m no longer paralyzed by the fear of failure. Which may, in itself, may be the greatest success of all.