How To Take The Entrepreneurial Leap


Photo Credit: iStockPhoto

Photo Credit: iStockPhoto

(This is part 1 of a 3 part series.)

So you’ve decided you want something more out of life than just the typical get up, drop the kids off, go to work all day, pick up the kids, dinner, then bedtime routine.

You want more time with your children, but still have a professional life.

You want to be a Naptime CEO!

But how do you even start?

In this post I’ll take you through the key decisions you’ll need to make, your options, and what I did (and why you shouldn’t do that). The rest of the series will go into more detail about each of your options.

Key Decisions

First, what does your current work situation look like? Is it very stable and you enjoy it but you simply want more free time to be with your children? Is there a lot of uncertainly and layoffs? Or are you in a toxic environment and need out as quickly as possible? This will help determine how much time you have to transition into your Naptime CEO role and what business options will be most viable for you.

For me, I enjoyed my work, but didn’t have enough to keep me busy all day because our department was going to be phased out over the next year. I also really hated being away from my infant 12 hours a day – a big driver for me.

Next, what do your finances look like? Do you know what a budget is and actually create and follow one on a monthly basis? Who is the breadwinner in your family? How much debt do you have? Understanding your financial situation will help you understand how much risk you are taking on and again decide which business options will be best for your situation.

When I resigned from my company I was bringing in 65 percent of our income and I had no idea how to actually create and follow a proactive budget that worked. I don’t recommend doing this. 🙂

Finally, how supportive is your spouse? This is a biggie. Spousal support can make or break your Naptime CEO endeavors. You really need to have a heart-to-heart with your spouse to understand what their concerns, fears, or questions are. The more thought out and clear your transition plan, the easier it is for them to support your decision.

In my situation, my husband was very supportive. I had done a lot of upfront work and he believed in me and my plan. I was actually the one dragging my feet because I was scared. He finally said I had until the end of the month to submit my resignation and we weren’t discussing it any more. So even though I wanted to take the leap to being a Naptime CEO, he had to give me a good shove.

Your Options

1. Pursue Your Passion This is the ideal situation if you have the time and financial resources. Invest in understanding what your passion is, who your market is, how you’re going to serve them, and then build your business on the side. Once your business is bringing in 50 percent of your current income, then make the move to leave your job and become a full-time Naptime CEO. This works well if you have 18 to 24 months to make the transition from full-time employee to Naptime CEO.

For me, while this sounded like a great idea, I didn’t have 18 to 24 months to make the transition. If I took 24 months to make the transition, my son would be 2.5 years old and half way to kindergarten! I needed a different option. (Although, if you’ve be hanging around my blog for a while you know that The Naptime CEO is my personal passion.)

2. Grab the Lowest Hanging Fruit This is the most common option I see women take. You look at your current skill set and even what you’re doing right now in your career and figure out how you can do that for yourself. If you’re in accounting, can you find a handful of clients you can do accounting work for? If you’re in HR, can you provide HR services to companies that are too small to have their own HR department? I even spoke with another mom while we were chaperoning the second grade field trip to the museum last week about this. She is a manager for a large clothing retailer and loves doing the visual displays. We talked about how she could help smaller local companies improve their visual displays to increase revenues and inventory turns.

For this option, once you find a handful of clients willing to hire you, depending on your finances, you should be able to take the leap.

This was the option I chose eight years ago when I launched my consulting firm. I knew regional manufacturers needed help improving their processes and I had the knowledge and skill set to enable them to achieve those gains. What I did that you should NOT, even though I had my plan developed and my business legally set-up, I did not have a single client or even the hint of a client when I resigned. I just figured I would give myself six months to land my first project and through sheer will and determination it would happen. (It actually took me five months, but I still don’t recommend jumping without at least one or two clients!)

3. Self Preservation This is for if you are in the worst situation. If while driving to work in the morning you want to pull your car in front of a tractor trailer so you can spend a few weeks in the hospital just to get away from what is happening at work (if this is you, I’ve been there and I know the feeling), this is your option. GET OUT! Find another job while you work on launching your Naptime CEO endeavors. If that means you take a pay cut, go into a different industry, or have to take two jobs short-term, so be it. Your mental, physical, emotional, and spiritual health are much more important than any paycheck.

For me, a few years before I started my consulting firm I was so burnt out in my career I couldn’t even think about starting a business. I actually took a job working at the mall in a retail clothing store for a year. After that year though is when I started thinking about starting my own business. (Interesting fact: out of the 10 of us that worked at that store, 2 of us had Master Degrees.)

This should have giving you quiet a bit of food for thought. If you need help going through this process or just need someone to bounce ideas off of, let me know, I would love to help!

Next week I’ll dig into how to grab the lowest hanging fruit, since this is the most common option.

Here is Part 3 of the series How to Pursue Your Passion.

2 thoughts on “How To Take The Entrepreneurial Leap

  1. Pingback: Lowest Hanging Fruit | The Naptime CEO

  2. Pingback: How to Pursue Your Passion | The Naptime CEO

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