When to Hire Someone

How do you know it is time to hire someone to help in your business?  Many people advocate hiring everything out from the beginning while others think it is wise to do some of the work yourself so you learn the business and know what to look for and expect from your contractors, property managers and other people on your team.  Eric and I did a lot of the work in our business early on and we wouldn’t trade the experience of knowledge we gained from that time.  We had many hard days and late nights working on our properties, dealing with tenants, and countless trips to the hardware store.  This time taught us many invaluable lessons but now that we have started our family and want to travel more, we realize we need to hire others to handle most of this work.  It has been a difficult transition for us for many reasons:

  1. Why hire someone to replace something easy when one of us could do it.  Especially if hiring someone would cost $100 compared to us replacing a $10 part.

  2. The person hired won’t care as much as we do and might not do the job at the same level we would do it.

  3. Finding the right person is hard and we could have the job done by the time we get them in place and trained.

Making the transition has been a slow and challenging process but we are gradually getting better. We hired a property manager and are starting to transition our properties to their management. When we have a renovation we hire the majority of the work to subcontractors. We also hired someone to help us manage our social media posts so we can spend more time interacting with our followers and create more content than we would be able to do on our own. The process has been slow and gradual but we find ourselves gaining momentum each month that passes. 

The first step that helped us make the transition to hire others started with the delegate, eliminate and automate exercise I mentioned in the Wearing Many Hats post. Eric and I knew we didn't enjoy certain aspects of our work but didn't really come up with a plan until we sat down and wrote it all out. We realized we didn't enjoy placing and managing tenants and we could make more money and be more fulfilled by focusing on our book, podcast, mastermind groups, and other projects. By removing the stress that comes with managing the day to day rental business, we open ourselves up to opportunities to provide more value to more people and allow us to find a more purposeful life.

As we started the mental shift that we wanted to consider hiring others to help run our business, we often got bogged down in the fine details. How can we afford to pay someone? Who do we trust to take on the job? It is important to initially focus on the desired outcomes and eventually shift to the details. By starting with the big picture you can dream bigger and get closer to your dream life. We have built out our team gradually over time and added more responsibility to people as they show they can handle the job. We have always kept the big picture in mind and worked to delegate one task at a time. 

We have moved some work to the wrong person and had to work to course correct. We hired a virtual assistant company to help us take over some of the rental property management tasks we didn't enjoy. We found it wasn't a good fit for us because they needed the projects to be very routine each month and not all the tasks we wanted to delegate were things they could handle. After a few months of working with the VAs, we decided to hire a property manager and turn the entire management process over to them. It has definitely been an iterative process but we are happy with the result.

The book Who Not How had a significant impact on our transition to delegating work. In the book, Benjamin Hardy says “Results, not effort, is the name of the game. You are rewarded in life by the results you produce, not the effort and time you put in. All too often, there is a lack of commitment to results and an over-infatuation with “process” or “hard work.””  While our hard work served a purpose for us in our business, we realized we needed to focus on the results so we could expand our reach and help others.  If we had continued doing all the work on our rentals, we would never have created the podcast, book, and blog posts that will encourage others to make big changes in their lives.  Our purpose in life is to help others and Who Not How has been key in helping us on this journey.  Hardy also says “When the vision is important enough, the right team of Whos will come together.”  We have found this to be true countless times in our business.  When we were finally ready to relinquish control, the Whos magically appeared in our life.  


When we decided to write a book, we had no clue how to go about getting it published or any of the details of what we needed to do.  We mentioned this to a friend and fellow real estate investor who recommended we check out Self Publishing School (SPS).  They have great resources to walk you through the process from first words on the page to editing, publishing, releasing, and promoting.  We decided it was worth the money to spend on their programs so we could shortcut the writing process and not get bogged down in the details of how to self publish on our own.  If you are interested in self publishing a book, please contact Eric or me so we can share our experience with SPS.  We completed this same process for our podcast.  We could have invested the time in figuring out the cover art, intro/outro music, RSS feeds to send to Apple, Spotify, etc. or we could pay a company to take that on for us and focus on creating great content.  We decided Castos had the ideal program for us and we plan to leverage their services for many years to come.  If you are interested in launching a podcast check them out through our affiliate link here.

The biggest lesson Eric and I have learned is there are some jobs in life only we can do.  I am the only person who can be the mom to our child, wife to Eric, daughter, friend, and so on.  This realization has made it much easier for me to hire others to help in our business.  If given the choice between giving my time to my family and these critical roles or spending hours working in our real estate business, I know my decision is easily made.  Yes, there are many things in our business I alone can do or I chose to do, but I do this with the awareness that the task has an opportunity cost and I am willing to accept it.  We have decided to hire a team to help us so we can focus on the important things in life.  We started our business by working very hands-on in the business, but as we have grown into other ventures we choose to spend money to shortcut our process and buy more time freedom.

How can you make the time you spent reading this blog worthwhile?  Is it reading Who Not How by Benjamin Hardy and Dan Sullivan? Finding a few tasks you can delegate in the next month? or something else?  Don't let the time you just invested go to waste.  You only get one life so live it purposefully!


How can you make the time you spent reading this blog worthwhile?  Is it reading Who Not How by Benjamin Hardy and Dan Sullivan? Finding a few tasks you can delegate in the next month? or something else?  Don't let the time you just invested go to waste.  You only get one life so live it purposefully!

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Goals to Die For

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Overcoming Fear