Running in Boxer Briefs: My First 5k Race

On Sunday morning around 7:45am PST, I participated in the SF Marathon’s 5k. Thanks to my discovery of Vibrams Five Fingers and a strong personal desire to push myself physically, I’ve taken a liking to running, (which I used to hate) and enrolled in a 5k. Outside of a few minor setbacks, my training has gone well and my knee has not really bothered me, thanks to the forefoot running style I employ with the Vibrams.

It was my first athletic competition in over 2 years (since retiring as a national championship winning collegiate gymnast) and I had a lot of fun. I also ran it in just a t-shirt and boxer briefs. Here’s how it went down.

Final Days of Training

After my last hard training run on Monday (Runkeeper), my ankles were pretty sore (I’ve discovered I overpronate) so I took it easy – icing my ankles a lot and taking ibuprofen to manage inflammation. I did a short, easy run on Thursday just to keep my cardio fitness up – it was pretty warm and my pace was both slow and yet difficult (Runkeeper). Not a great start but it would have to do.

I find running with music really helps me push when I’m tired so I put together a special mix that was around 26 minutes – plenty of time to get past the finish line. See mix in the footnotes. I spent some time in the days before imagining the path I would run, visualizing runners along side me and my staying focused on my own pace and pushing through the hard points toward the end. Remember kids – visualization helps you master skills.

Rest & Diet

I knew I needed to get more rest and move my sleep schedule closer to race conditions. The race was around 7:45am and I’ve typically been sleeping around 2:30am and waking around 9:30 – 10am. I ended up getting decent sleep on Friday but Saturday I went to bed at midnight and woke at 6:20am – so not great.

I drank a lot of water and tried to avoid heavy foods the week of the race. Nothing like the need to perform at optimal physical conditions to cause you to eat healthier. I avoided beer and desserts and tried to eat more fruit. Avoided coffee and soda too, so that the Red Bull would have a stronger kick (see Race Day)

Race Day

Just arrived. The starting line hasn't crowded up yet

I normally run in a pair of board shorts that have pockets so I can stash my iPhone to listen to music while I run, but I recently picked up a nifty little thing called the SPIbelt, a super low profile iPod-holding belt so I could wear a lighter pair of shorts. It was cold the day of the race so I wore sweatpants, an extra shirt, regular shoes with socks and a bag to change into my race gear at the event.

Ate oatmeal for breakfast, drank more water + a couple Advils, tried to move my bowels in the morning (to get lighter and offset “runner’s diarrhea”) but no luck. Drank most of a Red Bull on the way to the subway because studies have shown that caffeine and taurine can increase physical performance and endurance.

Woops – Boxer Briefs It Is

Wearing my vibrams! And boxer briefs...

The SF Marathon 5k was held by the bay, along the Embarcadero. It was really cool to see so many people young and old lined up along the starting line. I already had checked in and got my race bib – it was attached to my Stanford gymnastics shirt which I wore to rep my school. I guess I also wanted people to know that though I like running, gymnastics was and always will be my first love.

Anyway, it was getting closer to the race and I wanted to get into my race gear. I stripped of my sweats, put on my Vibrams and took off my extra shirt. As I stuffed everything into the bag and prepared to hand it to the race coordinators for safe keeping, I noticed a breeze round my nether region. I looked down and realized I was only wearing my boxer briefs. Crap.

My thought process at that moment:

  • Dammit – I thought I had put my shorts on, what the hell??
  • There’s no way I can get to the apartment to pick up my shorts and get back in time to start the race.
  • I guess I could roll up my sweat pants and run in those. Boy that would sure slow me down.
  • Screw it – I didn’t train for a month and wake up at 6 in the morning to run a slow 5k. I’m running in my skivvies – let ’em stare!

And with that, the decision was made. I mentally pretended that I was just wearing thin, tight grey running shorts. I don’t know if anyone else bought into that particular illusion, but it helped me. No one I encountered said anything, including my photographers.

The Actual Race

Happy but freaking exhausted. Yes, I'm wearing my medal.

Wow – running in a crowd is very different from running by yourself. Weaving through tight spots, having to slow down to avoid bumping into others, judging your own pace – these things are difficult and take mental and physical effort to manage.

My rooommate Michael Righi had recently run a 5k and he mentioned how he got a little too enthusiastic at first and ended up struggling the 2nd half of the race. In recalling that story and considering my competitive nature, I knew I had to hold back a little and pace myself early on.

I ended up pacing a little too slowly – running around an 8:39 min mile when I should have been closer to 8 min. Even though I wasn’t that tired, I took a 20 second walk break at 10 minutes (and another at 20 minutes) to let my legs rest and catch my breath a bit, letting my sprint forward with more vigor.

In the last half mile, I really sped things up. I would target runners ahead and try to catch them. I passed a number of people toward the end which felt great. In the last 400 meters or so I broke into an all out sprint. It felt like I was holding my breath under a pool and seeing how long I could last before passing out. I could barely see anything when I crossed the finish line. Somehow I managed to not pass out before the finish line.

My last minute had me going at a 6:57 min/mile pace which for me is blistering and and according to Runkeeper at one instant I was actually going at a 5:39 min/mile pace. Wow – it’s cool to know that’s how fast I’m going when I sprint all out.

The Results

My final time was 24:33, which was a minute faster that my previous PR of 25:30 for a 5k. I was nowhere near hitting sub-20, which I ambitiously aimed for in the beginning of July. I think I’ve topped out on the quick training gains from just a few months of running and it will take much more work to lower my time further. Here’s my Runkeeper results.

I placed 86th out of 1673 competitors, 23 out of 123 in my division (Males 20-29),  neither of which is saying much since I’m sure there were tons of marathon and half marathon racers who could have smoked my 24:33 time without even trying. But being in the top 25% still feels pretty good given this is my first road race ever.

I picked up all the free food volunteers were handing out, got a photo with my medal andhad a free beer (Sierra Nevada brown ale) at 8:30am (hey – I earned it!) Then went back to the apartment to work on the startup.

Next Up

I really enjoyed the 5k and racing in general and if my knee, God-willing, holds up – I hope to be doing more of it. My ankles were definitely pretty sore the next day so I’m giving myself a bit of rest. My roommate got so pumped after hearing about my 5k that he wanted to go do another one this weekend. He wanted me to come and run with him – more for fun than for time. I thought about it, but decided it’s not my style. I could do a light run for training – but if I’m at the starting line of a race, I am not going to be holding back.

The next big target I have in sight is the 2011 Men’s Health Urbanathalon in San Francisco. I’ve seen ads for this race but didn’t quite understand what it was until recently – it looks like a lot of fun. It’s about 10 miles and held in New York, Chicago and San Francisco. The “Urban” part is that there’s a lot of running in the streets and a series of “obstacles” that force you to throw in some parkour moves (scaling a wall, swinging across a giant monkey bar – like thing, climbing over “crashed” cars).

I’m also thinking about Warrior Dash (which one of my friend’s has done and vouched for) and down the road – Tough Mudder.

If I do the Urbanathalon, I’ll be following a low mileage half-marathon training plan and throw in some body weight cross training on my off days. Will let you know how it goes. I might do some more 5ks or even a 10k in between now and the Urbanathalon which is early November. Let me know if you’re planning to do the race as well! We can swap training tips.


[Running Playlist] Kai asked me for my playlist in the comments. I had debated posting them since everyone has a different taste in music. But what the heck, here’s what I listened to. The race playlist officially cut off after 300 Violin Orchestra.

  • Ellie Goulding- Lights (Bassnectar Remix)
  • Britney Spears – I Wanna Go
  • Nayer feat. Pitbull & Mohombi – Suavemente (Prod. by RedOne) 2011
  • Ke$ha – Blow (Cirkut Remix)
  • Enrique Iglesias ft. Usher – Dirty Dancer (album version)
  • Basshunter – Angel In The Night
  • 300 Violin Orchestra – Jorge Quinetero
  • LMFAO – Party Rock Anthem (feat. Lauren Bennet & GoonRock)
  • Katy Perry – E.T. – Dubstep Noisia REMIX 2011
  • DROP IT LOW   (Remix)  Kat Deluna feat. Fo Onassis
  • Eminem – Till I Collapse – Dubstep Remix 2011
  • Far East Movement – Like a G6 (Eyes Remix)

[Photos of the run] Don’t scroll down if you dont want to see me running in my boxer briefs! You can really tell I’m sucking wind at the end there. Click photo for larger view.

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Jason Shen

Jason is a tech entrepreneur and talent expert. He is CEO of a performance hiring platform called Headlight, a Fast Company contributor, and an advocate for Asian American men. Follow him on Twitter at @jasonshen and subscribe to his private newsletter.

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Leave a Reply

  1. Jason,

    Awesome to see this summary. Congratulations on your first 5K. What was on your playlist?

  2. I wore a Stanford tank too! For caffeine, try the energy gel packets w/ caffeine – they are my godsend. Let me know if you’re up for a 5-10K in the city. I’m not training w/ my group until next year, but I’ll need to keep it up. My friend and I may do the Big Sur half in November. I’m officially addicted!

  3. @CatherinewithaC Ha – showing the Cardinal pride! =) I’m thinking about Warrior Dash which is a 5k (with mud and obstacles and stuff) but also some more normal races. Will keep you in mind! Let me know if you’re interested in WD.

  4. i have to say, some of these photos look suspiciously similar to some that Anthony Weiner also took. Are you trying to create your own Shengate?

  5. Congratulations! Just going through with the run when you didn’t even have the right gear is really impressive.

  6. @jackdanger Haha thanks! I’m not particularly shy about what I wear and I really just wanted to have a fast time. Whatever it takes, right?

  7. UFM Running Underwear has all the bases covered. Whether your preference is the Brief or the Boxer Brief, UFM Running Underwear for Men is designed with the Athlete in mind support system,, an internal conduit is tightened and a pouch is created.

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