Im in commercial insurance sales  (yeah, I know, evil sales person...Boo Hiss).

So, I occasionally do in-person cold calls to businesses.  

Instead of driving/CTA, I want to start cycling.  

My issue is that in the back of my mind I always wonder if people will judge me for being a cyclist.  

Do people view cyclist as losers that are unprofessional and unsuccessful?

Or does this belong in the category or "You shouldnt care what those types of people think"?

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haha, true! It's a process, but this city needs cycling. It's perfect for it. Ride safe!

I work at a law firm in the loop and haven't ever been made to feel less than for bike commuting. I would actually go so far as to say it's the opposite-- people are more often impressed and interested!  

I will say however, I put maybe an embarrassing amount of effort into keeping at least the illusion of looking polished (although on days like today I stand no chance) and also invest in a super reliable deodorant. 

Will people will judge me for being a cyclist?   In Chicago?  Yes, some.  In many other places in the world, no.

Do people view cyclist as losers that are unprofessional and unsuccessful?  Some people.  The unprofessional and unsuccessful ones, generally.

Does this belong in the category or "You shouldnt care what those types of people think"?  I think so.

On the other hand, how are they going to know that you cycled to your meeting?  If you're talking about wearing cycling clothes instead of what would be considered appropriate attire for the circumstances, then that's a whole other issue.

When circumstances permit, I go to business meetings on my Brompton.  I generally show up early, and freshen up and change some clothes if necessary.  A few times, I've had the bike out of view for the initial greeting, like behind something or in a closet in the reception area.  People have been pleasantly surprised when I retrieve the bike on my way out, or start carrying it with me behind them on the way to their office or conference room.  I just treat it as transportation, rather than a symbol of me being a "cyclist", like that's something different.

  

 When I commuted when I worked construction so it really did not matter how sweaty I got getting to work as I'd be drenched with sweat any way no matter what.

 But one spring when I restarted my commuting ways my boss commented,,, "you doing that shit again"

 Like I was not going to leave every last ounce of strength and energy on his job and "waste" some riding to work.

 When I got to work I was all fired up ready to tear the world a new butt hole and enhanced my job.

 I kept riding then even more just to piss him off.

Way to GO Manny !

 He had no clue back then as to my madness as my commutes was my only riding during the work week, on Wednesdays I did a 100 miles , 11 going to work then the rest afterwards after a nice 10 hour day digging ditches

 Back then I was competing in Ultra cycling and needed to be in shape for my bigger rides come the weekend and needed to ride no matter what.

 

If, when you arrive, your state (disheveled or not, etc.) meets what their perception of you should be, you are good to go...  If, for whatever reason, regardless of the bike, you do not meet their expectations for how you should look (or, how you would like the potential buyer to perceive you), you have a problem.

If it is a warm day, forget biking over for me - I would be a sweaty mess... Sheesh, even driving in A/C I might be a mess...

Just make sure you nail what YOU want their perception of you to be....

I too commute by bike to a law office. No negative comments. Lots of positive comments, including from my boss last week.
YMMV

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