We were not going to create the life of our dreams by focusing exclusively on our 9-5 careers. While we enjoyed being a preschool teacher and commercial banker, respectively, we did not love the limitations these jobs came with.

So instead of accepting our rank and file spot in society and relegating ourselves to 40+ years of Monday morning zombie-like states of pseudo enthusiasm and sarcastic office tropes like “just living the dream” – we decided to take matters into our own hands. Why anyone would choose to work for someone else exclusively when they can diversify and own more of their financial destiny is an enigma to us. The idea of having only one way to make money feels restrictive and risky – and so 20th century!

However, we were not die-hard entrepreneurs. We had limited life experience let alone entrepreneurial experience. We did not have any serious capital to invest or have any brilliant change-the-world ideas either! But we did have some money, we were coachable, and willing to work hard. So, with a moderate amount of time, money and skill, we inched our way into the game of moderate entrepreneurship (aka side hustling).

Fast forward 15 years and we have grown our first side hustle to several million dollars in revenue. We used the surplus cash to invest in public and private equities, real estate (commercial & rentals), and added some consulting. These successes compounded and led to coaching and mentoring others, public speaking to thousands a year, and chasing passion projects like launching our first non-profit and writing our book, So You Want to Start a Side Hustle.

We now consider ourselves full-time parents and entrepreneurs. Most importantly, we earned the autonomy to step away from our regular job life, become what we call “time wealthy”, and have the freedom to chase our passion projects, our children, and each other. 

We truly wish these choices and lifestyle upon all who are willing to embrace the adventure that is side hustling.

Unfortunately, many start with good intentions but tap out after the initial honeymoon phase – or simply do not make enough cash to significantly impact their life.  While there is an epidemic today of people starting side hustles, we pride ourselves in teaching people how to finish one.

In guiding many people how to become successful moderate entrepreneurs, we have noted several lessons and patterns – either from watching their failures or our own! As a result, we would like to share with you now, very directly, what NOT TO DO when starting a business.

Here are our top DO NOTs when starting a side hustle:

DO NOT wait until you discover your passion or have a brilliant world-changing idea to start.

There are exceptions but for most, this is silly and impractical. In fact, most business owners haven’t created anything completely original and make great money utilizing a business they may like, but are not passionate about (just like a job). So RELAX, we didn’t have to be inventors or visionaries like Steve Jobs to be successful—and neither do you!

  • DO consider taking a more practical approach and buying an existing business or using established systems like franchising, affiliate marketing, direct sales, or owning rental property, etc. Realize your first business doesn’t need to be your last!

DO NOT seek out business advice from those who have never built an actual business! This includes your loved ones, roommates, college beer or White Claw drinking buddies.

Realize, just because someone loves you does not make them qualified to empower you.

  • DO elevate the right WHO by identifying successful business owners already living the lifestyle you desire! We disciplined ourselves to stay focused on these said mentors or coach’s mindset, “Lifeset”, and “Brandset” — and it made ALL the difference.  (PLEASE DO NOT botch this!!!)
  • DO Identify a community of other entrepreneurs who can provide the guidance and likely emotional support you will need.

DO NOT think of your side hustle as a side hustle.

Nothing wrong with a modest amount of monetary investment but if your belief, desire, and resiliency are weak you probably shouldn’t start!

  • DO think of your business as a multi-million dollar enterprise–so you can make it one!

DO NOT wait for the timing to be perfect. It never will be. DO NOT spend excessive time consuming content, writing up elaborate business plans, researching, or overthinking.

Employees will often focus on perfection – while business owners focus on production.

  • DO get busy doing so you can learn something, muck it up, and get better. Take massive action and embrace experiential learning vs our societally conditioned academic learning. Employees are often driven by fear while business owners focus on their vision.  If it’s not going to severely wound, bankrupt you or put you in prison — get going!
  • DO lean into faith that whatever skills or knowledge you don’t have, you can learn.
  • DO embrace: The best way to learn about business ownership is to run one!

DO NOT quit your job or invest your life savings to finance your ventures!

It’s not that you can’t, it’s just you probably don’t HAVE to.

  • DO continue to succeed in your career and bank money for your retirement. We leveraged the surplus cash from our jobs as seed money for our businesses. Moderate entrepreneurship does require some.
  • DO consider offsetting a lack of capital investment or expertise by investing more TIME (AKA sweat equity). For every 1 hour at our job, we invested ½ hour to 1 hour in our business!

DO NOT set aggressive or unrealistic expectations about the loads of passive income and profits you’ll be raking in after year one.

  • DO focus on learning, adjusting and over time generating incremental amounts of reliable income that you can convert into passive-progressive income. People talk big about making money while you sleep, we started with making money while we napped.

DO NOT randomly start something to make some “extra income” so you can accidentally become profitable and gain an unplanned amount of non-specified financial success.

It is extraordinarily difficult to hit a target when you don’t have one!

  • DO, from the beginning, create a Life Vision by turning your WHYs into a clear destination with set metrics — this enables you to create a viable working plan to achieve said Life Vision. If you don’t know what the BLEEP we are talking about that’s normal, but it shouldn’t be. You can access an example of what we call a Life Vision on our website: tandemconsulting.co

While this is by no means an exhaustive list, these insights should help you in activating your best life through a side hustle.  Business ownership is not easy, but it has rewarded us with a life that has exceeded our expectations. We wish this same level of joy and happiness to you and your family.

Carrie Bohlig and Craig Clickner are a Midwestern wife & husband duo, who have developed over a dozen streams of income together ― all built as side hustles. Carrie’s background in women’s studies and preschool teaching merged with Craig’s background in finance and commercial banking provide a unique, broad, and at times comical perspective on what it takes to be a successful business owner in the 21st century. Their businesses include Tandem Consulting, ClickGlobal LLC, CC Global LLC, LWCB Holdings, and most recently their non-profit, Tandem Giving, Inc, to help children in need. Today, they speak to roughly 20,000-plus people annually and have created enough autonomy in their life to focus on what they truly value most; family, adventure and impact.

As featured in youngupstarts.com

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