I was in a seminar with people from different fields outside of real estate and I loved hearing their stories as they brought new perspectives to the room about sales. One of the topics we hit on was grooming or dressing for success. I want to relate a story that I found quite interesting and has stayed with me for years.
A good-old-boy, third-generation farmer from a long-established family in Ontario’s former tobacco country wanted a different career and had the desire to get into financial planning.
He thought it out and then went from farm to farm to see all his relatives and other people that were intertwined with his family for generations. He drove in his pick-up truck and wore his jeans and baseball cap. For six months, he called and called and didn’t make one sale.
In despair, he went to a family friend, a Dutch uncle, and asked him to tell him honestly what he was doing wrong.
The old-timer said, “You come in looking like us, acting like us and you are one of us. Problem is, we don’t want one of us, we want a professional.”
The man thought on it long and hard. He decided to make a change. He borrowed a friend’s car and started wearing his Sunday suit and carrying a briefcase. Slowly, he started to make sales. Eventually, the sales grew into a very successful business.
A very interesting story. I know that many of you believe that you can sell real estate wearing jeans and a baseball cap, and I acknowledge that you can – for the short game. But for the long term, the lesson this man related shows that being a professional is about image, about being your own brand, of dressing for success.
Are you projecting a professional image at all times or are you just “one of us?”

Barry Lebow, FRI, ASA, ABR, SREA, SRES, IFAS is an active Realtor and highly regarded real estate authority in Canada, who starts his 58th year in the profession in summer 2025.
Throughout his career, Barry has received numerous accolades from various real estate associations for his exceptional work in the industry. Although no longer an active appraiser, he maintains three recognized appraisal designations. Barry’s expertise extends to providing expert testimony in approximately 600 trials across North America, with his focus now on cases involving agents who are being sued.
Currently, he serves as broker of record at RE/MAX Realtron Robert Kroll Realty, Brokerage. For more information or to get in touch with Barry, visit barrylebow.com.