The Syrup – working on versus in your business

Before we dive into our next topic, I want to just say “thank you”.  I received countless emails, texts, direct messages and comments on the last edition, The Syrup – Mental Illness and Seeing the Unseen, from people who felt brave enough to share their own stories with me.  It deeply touched me and as a contributor to this publication for over a decade, I can honestly say this is the most feedback I have ever received on an article.  I’m glad it struck a chord with some and hope you felt a little more “seen” in this crazy thing called life.  

Our next topic was brought up by the legendary Eric Silverman, who is also a frequent BenefitsPRO contributor, podcast host and enhanced benefits guru.  He brought up the age-old topic of working on your business versus working in your business, something I think many entrepreneurs and business owners struggle with.  

Before we tackle this, let’s first define and clarify so we are all on the same page.  I think of working “in your business” as more about managing the immediate tasks and responsibilities necessary to keep the wheels on the bus, while working “on your business” involves strategic thinking and planning to ensure its long-term success and growth.  

Some examples that might make it easier to think about would be:

• Working In Your Business:  The hands-on stuff like selling or consulting on insurance, customer service, admin work and managing the day-to-day operations.  
• Working On Your Business:  The big picture work that looks more at the future, both near and far.  Things like strategic planning, market research for opening a new office location, business development strategy, marketing, and long-term goal setting.    

Some of the most successful people in our industry have found a way to balance these two approaches or to bring someone in to help.  Because let’s face it, not all of us are good at doing both.  If you are a person that is a bit of a dreamer and known to say things like “What would it look like if…”, then you are probably good with working on your business.  But you also need to have people in your company that who keep the wheels on the bus while you have your head in the clouds, or you won’t have the revenue coming in to implement your dreams and reach your goals. These are the “In Your Business” people.  Typically, your Type A’s that have to-do lists are the ones that are great on implementation and structure to hit your dreamer goals and can pull you back down to earth when you need a healthy dose of reality.  

Honestly, I can be a bit of both when I’m in the right environment and surrounded by the right people.  I love dreaming and I’m a taskmaster and a freaking machine when it comes to work, but I need the balance of others to run a successful company.  When we brought in Sean O’Rourke as CFO over seven years ago, it became a gamechanger for the company.  He has a much different approach, comes from outside the industry and was exactly what we needed to get us to the next level.  Our revenue has grown steadily year after year since I opened the doors in 2005, but his strategic approach and high-level thinking put us in a financial position where we didn’t even blink when a national pandemic hit.Andhe has pushed my business Partner, Colleen Blum and myself to think about taking on new opportunities, to grow our consulting arm and to become one of the leading  expert witness firms in the area we practice.  All because we have an internal balance within the company.  

One of my favorite things is when the three  of us are brainstorming, because you get the logic, the passion and the money aspects looked at and it makes for a better way to set and accomplish goals, both short and long term.  

I know many readers are sole props who are struggling with doing it all and figuring out how to take things to the next level. To be honest, you probably can’t do it alone.  Eric and I talked about this recently and discussed how many business owners talk about not being about to afford bringing someone in.  We both remembered when we made the decision.  Eric said he had the same mindset 20 years ago, but “Once I finally made the leap of faith to hire someone to help, my business took off like a rocket.  Making the decision was the hardest part.  But once the decision was made, the ‘doing’ became effortless.” 

As I close out this edition of The Syrup, I’d like you to think about when Eric made his leap.  Very rarely does an entrepreneur have someone come up to them and hand them a few million dollars to start a company.  Most of us started our businesses on sweat equity and the change from our couch cushions.  And while moxie and grit can get you far in this industry, also remind yourself to be smart enough to know what you know, and to know what you don’t know.  Check your ego and bring in people who aren’t just like you, but can help you soar; most successful business owners find a balance between working In and on their business, as both are crucial for the overall health and sustainability of a business. And at the end of the day, isn’t that what we all strive for?