My 30-Day Mission to Finally Master a Push-Up

Every winter, I use my family trip to a remote, beach in the Bahamas (a total Wi-Fi dead zone) as motivation to get back into a regular workout routine. I start each morning with a 7 a.m. run and strength-training circuit, pouring sweat as I crunch and lunge in 90 percent humidity beneath the beating sun. Go me.

But even as I tack on more distance or add another set as the days go by, there's one exercise that always eludes me: the push-up. Every time I try to do one, I fail. And I'm not being self-deprecating. I literally can't. As I slowly bend my elbows, lowering my nose to the floor, I hit that ascension turning point…but nothing happens. Shaking, my arms collapse and my body slumps to the ground. I lie there in a heap, feeling like an embarrassment to all womenkind.

After yet another year of working out every day and taking endless amounts of commentary from my sister ("Seriously, Katie, you can't even do one?"), I decided enough was enough. New year, new upper-body strength. But since I've tried and failed before (though if I'm being honest, I've become the girl in the workout class who goes straight to modified push-ups before even trying one regular push-up) I decided I needed professional help to give me the boost I needed to finally master the elusive push-up.

"Let's face it, push-ups are hard," says Holly Rilinger, a New York City-based Nike Master Trainer and founder of LIFTED. "You're literally pushing all your weight from the ground while maintaining stability through the body." (Holly is the trainer behind our 30-Day Push-Up Challenge.)

What I needed, Holly said, was to build up my pectoral chest muscles, but also strengthen other muscle groups: "Core stability, quad strength, and triceps are all required for a perfect push-up." So I asked her to craft a flexible program that would work me up to the perfect push-up, but that wouldn't interfere with my hectic work schedule — something I could do at home with minimal equipment.

So I committed to her three-day-a-week plan for four weeks. This is how I fared.

30-Day Push-Up Plan

Week 1: Day 1

The workout: 2 rounds of 12 modified push-ups, 12 bodyweight squats, a 30-second elbow plank, and 10 triceps dips, with 30 seconds of rest between exercises.

I wake up at 7 a.m. to realize I am in my cold, New York City apartment and not in the Bahamas. Crap. Well, I guess let's get started.

I breeze through the modified push-ups (and by breeze I mean I hit number five and thought to myself, I hate push-ups-why did I agree to do this?). Twelve squats, easy. Plank, never enjoyable. Triceps dips — I'm gonna need a heavier chair because this Ikea piece of crap keeps sliding out from under me. As I finish the second set, I feel accomplished. Maybe I really will master the push-up.

Week 1: Day 2

The workout: 2 rounds of 15 modified push-ups, 12 bodyweight squats (add dumbbells), 12 triceps drips, 60 seconds of side-plank (30 on each side).

Holly's upped the ante. Did I mention I can't do side-planks either?

I work my way through the modified push-ups, pausing slightly after number eight (I'm bad a math, but I think that's more than halfway through). All in all, not so terrible. The bodyweight squats I don't mind, but I'm pretty sure I forgot to keep my chest up. Will perfect that on round two.

Side-plank time: I have to put one foot in front of the other just to stay afloat, but I make it through. After that, I try using my coffee table for the triceps dips but remember it was a wobbly-legged hand-me-down from my sister. Mental note to unscrew one of the legs on her coffee table next time I stop by her apartment.

As I wrap up the second set, I'm not really impressed with my performance. But no time to criticize. I need to get in the shower.

Week 1: Day 3

The workout: 15 modified push-ups with shoulder taps, 12 tempo squats (descend for 3 seconds, hold at the bottom for 2, then raise back to standing), 10 walking planks, and 15 dips. Rest 30 seconds between exercises and repeat for a second round.

Is Holly crazy? I was supposed to do this one on Friday, but it's winter, and wine on the couch beat out my desire to exercise. So, on Saturday morning, I head to my weekly HIIT class at Exhale and promptly curse myself for not having done this routine yesterday, since my body is now wiped and the last thing I want is extra-credit exercise. But I know if I skip now I'll never recover.

Knees on the floor, I descend in the push-up position, raise back up, and tap…tap. I make it to eleven-and-a-half and decide my body just feels too heavy. That's good enough, right? (I know it's not.) The tempo squats I quite like. Just think, Ass getting stronger. Ass getting stronger.

Time for walking planks. Holly wrote that I'm to start in a high plank and then lower one arm at a time into an elbow plank, then raise back up to a straight-arm plank. I've done these before in barre class, I realize. The lowering isn't so bad, but getting back up…the struggle is real. And I definitely moved my hips way too much.

Fifteen dips and I'm out. Oh, wait, two rounds. UGH.

Week 2: Day 1

The workout: 5 full push-ups, 30 seconds of wall-sits, 10 modified triceps push-ups, and a 30-second high plank with shoulder taps. Rest for 30 seconds between exercises and repeat for 2 rounds.

This week, the training wheels come off. As I start my big-girl push-ups, I make it three-quarters of the way down to the floor and chicken out, raising myself back up. I don't want to fail. I cannot have another house of cards moment. I decide to do three half-assed push-ups and two full-tilt modified ones. At least those are getting easier.

The rest of the routine goes well. Quad exercises, I realize, are much easier for me. If only this were a squat challenge. The modified triceps are a bit awkward, but the high-plank shoulder taps are much less painful than the time I had to lower down to the floor. (It's the small victories in life, people.) I try to focus on form and am confident I kept my hips square and in line with my shoulders.

Week 2: Day 2

The workout: 15 dumbbell triceps kickbacks, 1 minute of wall-sits, 10 negative push-ups, 5 full push-ups. Rest for 30 seconds between exercises and repeat for 2 rounds.

Today I learned a fancy new move: "negative push-ups." These require lowering to the ground from the push-up position for four seconds, then returning to the starting position. "The work here is controlling the eccentric contraction," she outlined. I promptly googled and discover this means "controlling the motion of an active muscle while it's lengthening under load." Here's roughly how it went:

Push-up 1: Descend, descend, descend, descend. Knees to the floor, raise back up. Not so bad.

Push-up 2: Descend, descend — this hurts — hover, descend.

Push-up 3: Hover, descend, hover, descend.

Push-up 4: Hover, down an inch, down an inch, down an inch. Pretty sure that was cheating.

I more or less continue at this self-determined pace until I reach 10. (Okay, nine.) I'm too wiped out from my attempt at the whole negative thing to do the regular push-ups.

Week 2: Day 3

The workout: 5 full push-ups (as many as you can, and finish with modified), 15 dumbbell squats, 12 modified push-ups with a side-plank rotation, 45-second wall-sit, and a 45-second plank. Rest 30 seconds between exercises and repeat for 2 rounds.

TG no more negative push-ups — they remind me of Chaturanga, which of course I can never do in yoga class. This workout didn't go terribly, but the side planks did not go well.

Week 3: Day 1

The workout: 7 push-ups, 15 squat jumps, 15 modified triceps push-ups, and 60 seconds of side-plank with hip taps (30 seconds on each side). Rest 30 seconds between exercises and repeat for 2 rounds.

It's like this woman is trying to kill me; it'll be death by side-plank, I swear.

Week 3: Day 2

The workout: 8 full push-ups, 1-minute wall-sits, 20 triceps dips, and 12 negative push-ups for 4 seconds each. Rest 30 seconds between exercises and repeat for 2 rounds.

More negative push-ups? Oh goodie, my fave. Dreading the torture to come, I start my routine pondering how quickly I can count to four — wait, did I just do a push-up? I was so distracted, I didn't even realize the rock-solid move. Holy shit. Is this actually working? I lower down a second time and, without hesitation or trembling arms, shoot back up. I make it to five regular push-ups before lowering to my knees to finish out the set.

Week 3: Day 3

The workout: 9 full push-ups. Rest 30 seconds and repeat.

Thoroughly confident, I'm excited to challenge myself in today's program. I lower and raise, lower and raise with control and at a steady pace. I decide to focus on form and switch to modified after six.

Week 4

The workout for each day this week: 10 jump squats, 1-minute plank, 1-minute wall sit, 15 push-ups with side-plank rotation, 15 dumbbell squats, and 10 full push-ups (as many as you can complete, finishing with modified). Rest 30 seconds between exercises and repeat for 2 rounds.

We're in the home stretch and the intensity is heightened. I make it through days one and two and have to make some modifications, and am ready for the final workout. As I start to jump, I feel sluggish. After moving into the plank position, I make it 30 seconds before collapsing to the floor. I'm supposed to crush this workout, I think to myself. Did I really do all this for nothing?

My phone rings-saved by the bell. It's my sister: "Hey, do you wanna go to Barry's with me on Saturday?" I start to speak and then, "Oh wait, it's arms and abs day, you probably won't wanna do that, since, well, you know…"

I tell her I'm in the middle of something and have to call her back. Reignited by my desire to prove her wrong, I head straight into push-ups with side-plank rotations. I slowly lower down to the floor, raise back up, and twist. Lower down, raise back up, and twist. I complete the first set of exercises, turn up my headphones, and power through to the third.

It wasn't perfect — I definitely sagged my hips and wobbled around at times. But as I lowered down into my final push-up, I paused above the ground — oh God, here goes my house of cards — wait, I muscle my right arm up an inch, then my left. Raising up in four, three, two, one — look, a positive push-up. Mission accomplished.