Most of you reading this post already know that being a self-employed real estate person is not all about calling your own shots, freedom, glamour and opulent riches. Being a self-employed anything is hard work that requires enormous self-control and self-regulation.

Being a self-employed real estate professional requires much more of that self-control and self-regulation…it requires real knowledge, real skillsets and enormous interpersonal savvy to both create and build trusting relationships that will encourage your clients to essentially “sign on the bottom line” for one of the largest financial transaction of their lives.

For those of us who are transitioning from having a “programmable 9-5 job” with a steady paycheck to becoming a self-employed real estate professional, G. Brian Davis outlined some of the challenges involved with that transition for

  1. Davis calls it the Fun or Romance Factor.
    1. Clearly, there is a difference between “romance” and “reality. The romance of being self-employed, being “your own boss,” doing things the way “you want to do them when you want to do them” are romantic fantasies of being self-employed. The reality of being self-employed is that working for yourself is a grind.
    2. Sitting in an office somewhere or in your house all day long is NOT ROMANTIC.
    3. Figuring out the most profitable things to do every day is NOT ROMANTIC.
  2. Discipline
    1. Figuring out how to PROFITABLY spend your day is one thing…doing the things that will make your day profitable REQUIRES DISCIPLINE.
    2. Being a self-employed real estate professional means that no one will tell you what or when to do what is required. Being self-employed means that you are in charge of your own discipline.
  3. Lonely?
    1. There is your desk, your computer and your phone. That’s it…no water cooler or break room for chitchat.
    2. Sit up, stand up, walk around and GET TO WORK.
  4. Health insurance
    1. There isn’t any health insurance for self-employed people so price out what it costs to get health insurance for you and your family.
    2. Of course, if your spouse has health insurance, that’s a different story.
  5. Lifestyle Flexibility
    1. There isn’t any in the beginning and at times, there isn’t any in the middle or later times due to self-employed people having lean months…every self-employed real estate professional has lean months.
    2. Luxury gets redefined…going to a movie becomes a big thing.
    3. Is your spouse/partner willing to pare down?
  6. Friend/partner/spouse backlash
    1. As a self-employed real estate professional, it could take weeks/months/years to generate “enough” and/or “regular” income. Everyone who cares for and about you wants to be supportive but, for how long?
    2. Be prepared for ongoing talks/fights about money.
  7. Living with Uncertainty and Anxiety come with the territory.
    1. You will be at least twice as nervous/frightened about finances as your friends/partner/spouse.
    2. Unless you are already financially independent, worrying about finances is a perfect recipe for self-doubt.
  8. Having Emergency Funds
    1. Brian Tracy, the motivational speaker and self-development author, said, “People who live full lives will have an emergency pop up every 3-4 months on average.”
    2. Don’t be surprised…emergencies cost money so have enough emergency money in reserves.
  9. Qualifying for loans
    1. As a real estate professional, you’ll come across opportunities that will stimulate you to become a real estate investor.
    2. Have several sources of income/financing lined up so you can take advantage of such opportunities without having a W-2.
    3. Know the loan rate and alternate documentation required for someone without a regular income and/or pay stubs.
  10. You Need Routine and Structure.
    1. 9-5 jobs come with routines and structure. As a self-employed real estate professional, you need to create that structure and routine.
    2. Work backwards from your goals to set up routines for yourself just as you would if you were planning on running your first marathon.
    3. Be ready with your new structure to fill any voids in your life now that you are on your own.
    4. Build new relationships and develop them. 

Thanks to G. Brian Davis and

As you’ve already surmised, signing up and being responsible to real estate coaching can go a VERY LONG WAY in doing all the above and becoming the successful real estate professional you’ve dreamed of becoming.


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