the "Alan" May Challenge

Real Estate Agent with Jameson Sotheby's International Realty

Cathy Streib and Carol Williams are throwing a May Active Rain Challenge. I, of course, had to turn it into an Alan May Active Rain Challenge.  Here is mine.

  1. What was your first job
    My very first paying job was delivering papers.  I had two routes where I delivered about 200 newspapers daily, via my trusty banana seat stingray bicycle.  I was also tasked with collecting the money from the subscribers, which proved to be the worst part of the job, and the reason I eventually quit.
  2. How long have you been in real estate?
    On some days, it seems as though it's been eons, and other days I feel relatively new.  But I actually started right around the turn of the century.
  3. What is your biggest fear and what have you done to try to overcome it?
    Yeesh!  I don't know that I actually have a biggest fear.  I don't love heights, but I'm not acrophobic.  I don't love snakes, but I'm not Ophidiophobic.
  4. What would you do, if you knew you wouldn't fail?
    Vegas, here I come.
  5. What is a habit that you would love to eliminate or change?
    Well, it used to be biting my nails, (I used to chew my nails 'till they bled) but I conquered that many years ago.  I've always struggled with my weight, so I guess the habit would be overeating.
  6. What's your favourite meal?
    This one's easy for me.  Filet Mignon, baked potato and asparagus with butter... accompanied by a Vodka Martini, - shaken hard, with olives (multiple) .. and Tira Misu for dessert.
  7. What is something you wish you'd done?
    I wish I'd travelled more.
  8. Who has been most influential in your life?
    This one is tough. There have been a lot of influences in my life, good and bad.  I'm going to have to go with my dad.  A great deal of who I am as an adult, is due to my father.
  9. What are you favourite business-related books?
    I don't have any. I don't read business-books.
  10. Other than business books, what are your favourite things to read?
    I love to read historical novels.  (ie: James Michener, Ken Follett, Jeffery Archer, Jean Auel)... you get the idea... I also love science-fantasy (ie: Lord of the Rings, Asimov's Foundation Series)
  11. What are your top five favourite movies?
    1) the Shawshank Redemption
    2) Dances with Wolves
    3) Saving Private Ryan
    4) the Wizard of Oz
    5) Braveheart
  12. If I came to your city to visit for one day, what is the one thing that I must do or see?
    Ohmigosh, this is Chicago!  One thing?  Really?  If I had to choose only one thing, I would suggest taking the Chicago River Boat Architecture Tour.  It gives you the chance to take a leisurely cruise (literally) down the Chicago river with a narrated education of many of the iconic skyscrapers that make up downtown Chicago.  It's an eyeopener even for the locals.
  13. If I came to your city to visit for one day, what is the one restaurant you would recommend?
    Well, that would depend on the type of food you enjoy.  Chicago is a serious restaurant town.  If you're a steak eater, I would recommend Gibson's.  One of the great Chicago steak-houses.  If you like high-end asian, I recommend LeColonial.  Amazing high-end Vietnamese food that leans heavily toward France.  White linen table clothes, waiters that scrape the crumbs away, heaven wrapped in banana-leaves.   If you like trendy and delicious, I recommend The Girl and the Goat.  Stephanie Izard's incredibly creative restaurant that allows you to eat foods you would rarely consider.
  14. If I was going to relocate to your area what advice would you give me that is unique to your area?
    I guess that depends where you're coming from, but in general, I think the best advice I could give when moving to greater Chicagoland is "buy warm clothes".
  15. Do you have any special talents?
    I can curl my tongue.  Does that count?
  16. Do you have any quirks?
    I can curl my tongue!  Does that count, again?
  17. What is your best character trait?
    I wear pants, now, in all of my zoom meetings.
  18. Have you ever done anything that you would never do again because it was too hard or too dangerous?
    Yes.  Almost everything I did between 18 and 21.  It's amazing that I'm still alive today.
  19. What is your favourite thing to do in your spare time?
    What is this "spare time" of which you speak?
  20. If you could live anywhere in the world, where would you want to live?
    I spent a few years living in Israel, when I was young.  I would live in the old city of Jerusalem.  It's not a religious thing... it's just an amazing city, steeped in history, and sacred to three of the world's major religions.
  21. What is something that we don't know about you that would surprise us?
    I'm shy.
Posted by

 ALAN MAY, Realtor®   
Specializing in Evanston Real Estate and North Shore Real Estate

Jameson Sotheby's International Realty, 2934 Central Street, Evanston, IL 60201
Office: 847.869.7300      Cell: 847.924.3313      Email:

Evanston Real Estate & North Shore Real Estate
Licensed in Illinois


Comments (12)

Ray Henson
eXp Realty of California, Inc. (lic. #01878277) - Elk Grove, CA

It was fun learning a bit about you.  I enjoy many of the same authors and movies as you, all good choices.  I will second the recommendation to go on the architecture boat tour.  We did that an enjoyed it a lot.  You definitely need a big jacket for that one.

We are going to Israel at the end of June.  It is a bucket list item for Mary Margaret.  It will be a short, quick, guided vacation.

I would share that favorite meal with you.  Delicious!

May 23, 2022 09:04 AM
Alan May

Israel, at least for me, isn't a "quick visit" option.  I have too many people/places to see... I need a minimum of 3 weeks.

May 23, 2022 09:06 AM
Kathy Streib
Cypress, TX
Retired Home Stager/Redesign

Alan- thank you and you did not disappoint!!!!  let's just get this out of the way...I too can curl my tongue...could we be a traveling road show???

Our dear friend's passion was volunteering with his wife in the Israeli Army. He did this for many years for two to four weeks at a time. His wish was to live there half the year. 

May 23, 2022 11:39 AM
Alan May

That could be problematic.  You could be risking your American citizenship by volunteering for a foreign army.

It's different if you're a dual-citizen and you're drafted, but if you volunteer... I'd be very careful.

May 23, 2022 12:41 PM
Hannah Williams
HomeStarr Realty - Philadelphia, PA
Expertise NE Philadelphia & Bucks 215-820-3376

Alan May One of my dear friends just moved to Isreal. She said more American move there than Florida 

May 23, 2022 12:55 PM
Alan May

Hannah Williams I researched your statement, and your friend isn't correct. 

In 2021 about 330,000 Americans moved to Florida.  In the same year only 3,168 Americans immigrated to Israel.  Not even a close call.

May 24, 2022 04:58 AM
Cara Marcelle Mancuso
Golden Girls with SW Desert Homes - Tucson, AZ
Call a Marana neighbor, I'm THERE!

I LOVE the Chicago River tour....can't wait to take my husband one day soon.  It's always so fun to read your posts -- thanks for sharing.

May 23, 2022 01:09 PM
Alan May

I've taken the tour a handful of times... and best part is one of my colleagues, from my own office, was the docent who was giving the tour.  Fun.

May 24, 2022 04:58 AM
Kathy Streib
Cypress, TX
Retired Home Stager/Redesign

Alan- I don't know what his status was but he went with a group every year. His dream was to have dual citizenship but sadly he passed away several years ago. Each year he opened his home to a group of young tennis players from Israel.

May 23, 2022 07:09 PM
Alan May

I'm sorry for his passing.

May 24, 2022 05:00 AM
Carol Williams
Although I'm retired, I love sharing my knowledge and learning from other real estate industry professionals. - Wenatchee, WA
Retired Agent / Broker / Property Manager

Hi Alan,
I'm not a martini fan but I do love extra olives in my Bloody Marys.  Jerusalem is one of the most fascinating cities I've ever visited... Israel in general is fascinating.  I have taken that Chicago river boat architecture tour. It was a beautiful day and an excellent tour. I would do that again.

May 24, 2022 06:23 AM
Alan May

Martinis are definitely an acquired taste.  My father-in-law acquainted me with them.  ;-)

May 24, 2022 11:27 AM
Anna Banana Kruchten CRS, Phoenix Broker
HomeSmart Real Estate BR030809000 - Phoenix, AZ

Hi Alan what a fun read.  You shy?  I would never have guessed that with your quick sense of humor.  Love the idea of the boat architecture tour. I toured the Frank Lloyd Wright home and enjoyed that - boat tour would be more fun I think.  You sound like a couple of my brothers - lucky to be alive after doing stupid stuff when they were really young. Somehow you all managed to grow up!  Really fun read!

May 24, 2022 10:00 AM
Alan May

We would never tolerate our own children doing half of the stuff we did as kids.

May 24, 2022 11:27 AM
Debe Maxwell, CRS | The Maxwell House Group | RE/MAX Executive | (704) 491-3310 - Charlotte, NC
The right Charlotte REALTOR!

You're a$$!! LOL

Loved your answers and chuckled most of the time. There are things that I did as a young adult that makes me also ask, how on earth am I still here?!! 

If I ever come to Chicago to visit, I would call you - you are an amazing agent and I am sure you would be a fabulous guide. The architectural tour sounds fabulous to me.

BTW, Ryan is moving back next month. I'm sad to see him leave NC again but, his heart is in Chicago. If he ever settles and buys, you know we'll be reaching out to you! more thing, I can curl my tongue too - is that not normal?! LOL

May 31, 2022 09:30 PM
Alan May

I dunno if it's normal... seems to be in my family.  My older sister was able to curl her tongue and also able to touch her tongue to the tip of her nose.

Jun 03, 2022 06:24 PM
Ed Silva
Mapleridge Realty, CT 203-206-0754 - Waterbury, CT
Central CT Real Estate Broker Serving all equally

You are right about so many things to do in Chicago. I always like going to Lawry's for the special way they serve their beef, and one would not expect you to be shy f the prolific way you write

Jun 01, 2022 06:07 PM
Alan May

I dunno... Lawry's isn't what it used to be... there are so many steak houses that are so much better.

Jun 03, 2022 06:25 PM
Tammy Lankford,
Lane Realty Eatonton, GA Lake Sinclair, Milledgeville, 706-485-9668 - Eatonton, GA
Broker GA Lake Sinclair/Eatonton/Milledgeville

If that's the actual cruise ship.... no thanks, way to crowded for me. you are NOT shy and we had the same answer to #19 which I find hysterical with all the dates we seem to have in common.  Oh and I've never ever seen the wizard of oz.

Jun 03, 2022 11:44 AM
Alan May

Nope... the cruise ship goes out onto the lake.  This is strictly the river cruise... much smaller boat, and far fewer people.

Jun 03, 2022 06:25 PM
Lyn Sims
Schaumburg, IL
Real Estate Agent Retired

Agree on the boat tours - great way to see the city. I thought you didn't do these type of posts?

Jun 03, 2022 12:31 PM
Alan May

I don't.  This is a figment of your imagination.

Jun 03, 2022 06:26 PM