Chicago Mountaineering

Comedian Gail Forrest moved to a beautiful 3rd floor apartment in Chicago, and now must navigate the snowy ascent like a Sherpa.

I just moved to a new apartment and now surprisingly find myself in training for a whole new career – Sherpa. I couldn’t resist the vintage charm, large rooms, and perfect location of this place – a block away from Whole Foods to the West and Lake Michigan to the East. I felt like I had hit the housing jackpot. At the time, I completely ignored the fact that it was on the third floor in a building without an elevator. Big deal no elevator, right? Wrong. I also forgot about winter in Chicago as I hadn’t experienced one in ten years. Winter in Chicago may as well be winter in Nepal. I think they are interchangeable which makes my training possible. 

Winter in Chicago may as well be winter in Nepal

There are two ways up to my apartment: the carpeted front door stairs which, like a gentle hill, climb up to the third floor, and the back outside stairway which is Everest-steep, metal, and treacherously slippery when wet with snow. It appears to disappear “into thin air” until it reaches my back door. My parking spot is at the bottom of that stairway. It’s dreamy to have parking but not when it’s the descent from hell to reach your car in winter. Dogs are only allowed in and out on those stairs and yes, I have a dog.

My Sherpa training days begin with what I need to wear to make the trek from my apartment down the back stairs and head west to base camp — Whole Foods. It takes me 15 minutes to put on enough clothes to venture out.  I wear my Uniqlo long underwear on top and bottom (no La Perla lacy bra and panties like Sandy Hill, the socialite who attempted Everest wearing the sexy undergarments), a heavy J Crew knit sweater, my  go-to Gap sweat pants, thickWigwam wool socks and ankle-high Timberland boots for starters. Then comes a lightweight down jacket from J.O.T.T. and last, but definitely not least, my North Face winter-weight down coat. My mittens are good to thirty below, or at least the salesman at REI said they were. I have an old pink wool hat which is my attempt at style given the rest of the outfit. My face warmer covers me up to my eyeballs and fits over my Covid mask. I can barely breathe or move, but trudge onward.

I carry cases of wine for strength training and to mentally toughen up in order to stop crying when scaling the back stairs

Sherpas are a freakishly strong and resilient group. They must carry an unbelievable (70 lbs on the recent winter summit of K2) amount of weight on their backs in technical gear, tents, food, and supplemental oxygen up to base camp and beyond. I carry cases of wine for strength training and to mentally toughen up in order to stop crying when scaling the back stairs.

This east ascent with bags of food leaves me gasping for air and wishing I wasn’t hungry. I don’t feel the need for supplemental oxygen but I am thinking of fixing ropes on the railing in order to bring sustenance up more easily. I’ve also considered staging a little wine bar on the second landing as a place to rest and re-consider why I rented an apartment on the third floor. Was I hung over or high?

Up to this point I do not need crampons when plowing my way through the latest snowfall to Whole Foods. I must, however, remember to check Amazon for them as they might make it easier to stay on my feet over the ice-glazed sidewalk. I slipped and nearly wiped out a Cocker Spaniel and his owner the other day but at the last second caught myself and prevailed. Harrowing, but a victorious moment in my training.

I’m afraid my little rescue dog Tulip is not happy about her new third floor home or the winter. She dreams of the South of France not Nepal. She loves running on the beach not scaling a snowbank. Poor Tulip cannot figure out where or how to pee or poop in snow.  Without a blade of grass in sight or smell she stands, stares at me, and looks longingly back at the door. Snow is not in her job description as I adopted her in LA. 

She also refuses to see the west ascent to the back door as an opportunity to live the life of a St. Bernard or Newfoundland. I am thinking the best way to get her up without a fuss is to “short rope” her so I do all the work and basically pull her up the stairs. It is a useful method to avoid great risk to a less experienced or endangered climber. She definitely isn’t experienced on uncarpeted stairs.

My friend Diane has tried both the east and west climb since I moved in. She made the gently rolling hike from the front door without being short roped, a need for supplemental oxygen, or longing for a wine bar on the second landing. The east stair climb nearly called for an ambulance or St. Bernard; whichever could get there faster! Clinging to the railing half way up she reached into her pocket for her inhaler as her breath was becoming more shallow. My Sherpa training came in handy as I held her purse until she could breathe again. 

I decided to plant a victory flag at the top of the stairs and move.

We noticed that a number of the items listed here are now on sale. Should you need a Chicago sherpa outfit, now may be a good time to shop.


  1. I lived in Chicaago and experienced the third floor walk-up! I always had a gorgeous apartment, and a miserable climb up three flights with groceries, a leather bag and winter clothes. Some things just don’t change, so I finally moved out of state! Thanks for the memories, Gail!

    • Glad I could remind you ! Yep, some things never change and that is winter in Chicago….next year back to So Cal! Last one here for sure. Happy for you that you are in a better, warmer place.

  2. So where are you and when is it time for either bumping carts together at Whole Foods – or a drink in the newly opened restaurants? Mary

    • I am just down the street! Have been here for a few weeks, and all unpacked and set up. I walk every day but don’t do much else because of the plague that has befallen us. Had shot 1 and scheduled for two on the 19th after which I might feel a little relief. I rarely see anyone except Tulip. How are you? I won’t go out until after the second shot and bummed it’s too cold to sit on a park bench and drink! Soon. We can take a walk


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Gail Forresthttp://www.gailforrest.com
Gail Forrest recently started doing standup which she finds is a complete blast. Gonepausal is her blog and she has a book on Amazon by the same name filled with stories of her skewed, funny view on midlife and all its attendant surprises. Humor is the only way forward at this point.


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