February 14, 2020, marked the start of my third year of self-employment. The past two years of growing and running my business, as well as the year of planning leading up to the start of my new company, have been both exhilarating and terrifying.


There were days I knew with great certainty that I was on the right path, and other days when I wondered if I made the right choice to migrate away a specific title and paycheck (a.k.a: what feels like stability).


I often talk to working parents who are considering making the leap to self-employment. Almost always, they are trying to find a way to “balance” the desire to be present for their family members – partner, children, aging parents – and the desire to have a meaningful career. Self-employment can seem like a possible fix to a complex problem.


Self-employment certainly can be a wonderful way to find more balance (note, I did not say “perfect balance”). I have found that self-employment is a wonderful way to combine meaningful work and family demands, but it is far from perfect. (Don’t get me started on the complexities and costs of health insurance when you are self-employed!)


Before you make the leap, consider the following questions:


  1. Do you have a passion or interest that you can turn into a business? You don’t have to be passionate about what you select as your self-employment career, but it really, really helps. When things get challenging (and they will), it helps if you actually like – or love – what you do. Passion makes the hiccups and downturns in your business a bit easier to bear.


I often start with this question, because this is a place where people can get stuck. If you know the answer, congrats and move to step 2. If you don’t you probably fall into one of two camps: You are so disconnected from what you truly enjoy that you don’t know how to answer this question (that was me, circa 2015) or you believe your passion cannot be turned into a career. Challenge both of those answers.


If you fall into the first camp (what the heck am I passionate about?) then you are probably burned out and need to refocus on taking care of you. Try some self care and then try to observe when you fall “into the flow.” The “flow” is the place where time seems to fly by because you are so into what you are doing. Often the flow equals passion.


If you fall into the second camp, you too need to sit with a question: How you can leverage your passion into a career? One peer leveraged her knack for organization into an office and closet organizing company. Another friend turned her love of travel and art into a lucrative career offering custom high-end vacations to beautiful locations featuring time with artists and tours with art historians.


  1. Get Real: What is your realistic household budget that outlines what minimum income you need to run your house each month? When you think about a budget, think about what you can cut and still maintain a tolerable standard of living you as your start and invest in your business.


For example, when I launched Bright Blue Consulting, we had to cut back on eating out and we eliminated an expensive after school program for our kids – at least in the beginning. It was not fun to make the changes initially, but we got creative (and the kids missed their after school program much less than I had anticipated). As my business grew, we added items back.


I cannot tell you how many people freeze at this point. This is where the decision to leave the corporate paycheck gets real. However, how can you even consider self-employment if you do not really understand that the decision will mean to you and your family? (I also always advise that you speak with a financial planner before making the leap.)


Trust me, I understand the fear. I too was scared that our family’s monthly budget number would mean that I was stuck in the corporate world forever. However, the number can actually be empowering.


Once you know what you have to make each month to run your home, you can begin to back into the income you need to generate from your business. And, by knowing this number, you can also look at your savings or loan options to determine how long you have to ramp up your business.


  1. What lifestyle do you want for yourself as you start, grow and maintain your business? Many of the working parents I meet with are trying to find a way to make a good income and be more “present” with their kids. They hope self-employment will give them more flexibility. It can, but only if you are very deliberate about defining what you want that “balance” and “presence” to look like. There will be trade-offs, and knowing what life you want to have at each stage of your business (planning, growth, maintain) can be helpful when new challenges arise.


  1. What are the trade-offs you are willing to make? Trade-offs will present themselves throughout your business’ lifecycle. That said, they can be especially acute in year one as you begin to pitch your business and make decisions that can impact the speed of your growth.


I often tell people that the work you do in year one, may not be the work you do in subsequent years. You may need to take a less than ideal project to get in the door of a target company or you may offer a discounted rate to build your client-base or deepen your experience. You may have to take a project that has longer hours than you initially want, but the pay or client access is worth it. Knowing what you want from the first step (Get Clear) can help you retain your balance as challenges to that balance pop up.


For example, if being a “present” working parent is important, how do you want to navigate a client request that conflicts with a big school event, birthday or important milestone? Getting clear makes these sort of trade-off decisions a bit easier to navigate.



  1. What are you afraid of?As I wrote in this blog last year, fear is one of the great barriers standing between individuals and self-employment. Most of the people I meet with wrestling with the fear of what failure may mean for them and their families. And, most people have not spent a lot of time really diving into their fear and determining if it is indeed realistic or not.


Only when you really examine your fear can you determine if it is indeed real and develop strategies to overcome it. Only by naming it can you take away its power. So sit with the question and name it.


These questions will get you started on the path to evaluating self-employment. This is certainly not an exhaustive list, but I have found that these questions are the ones that are often the most meaningful as you design a future life for yourself and your family that includes self-employment!