Questions About Being Your Own Boss? Here’s My Take On It (Part One)

I asked some moms on the YML Facebook page if they had questions about being their own boss. They did, and I answered some of them below.

Yoni asks: Why are some so opposed to being self-employed? 

Because it’s scary. When you’re working for someone else, you don’t realize how incredible it is that money appears in your bank account on schedule. That (if you’re lucky) you have insurance and benefits. There are a lot of benefits to being a 9-to-5er.

But once I got a taste for how cool it is to make your own schedule, it changed my life. I’m still overworked, but there’s flexibility in my days that is priceless. I can go grocery shopping at 11 a.m., make a decent lunch, take a nap if I want to (and if my son decides to sleep as well), take my kids to the park. Currently, I fit my work around my kids, whereas before I fitting my kids around my work. Make sense?

Erica W. asks:  How do you calculate if it’s worth it to leave a salaried position? 

Before I got laid off, I set a goal that I wanted to be self-employed by the time my daughter entered kindergarten. But looking back, I realize that I wouldn’t have been able to make that leap because I wasn’t planning it out correctly. Here’s my tips for determining if you can make that leap:

  • What benefits come with your job that wouldn’t be easily replaceable? If you are a single mom with insurance at your job and you have a child with special needs, you might want to stay put in order for your child to get the best medical care. If you are part of a two-income family and you both have insurance offered as your job, then it might be more feasible for you to strike out on your own.
  • Do you have at least one year’s worth of savings? Someone people advise that you have an emergency fund that is six months worth of expenses, but I say go for broke and fund that baby for a whole year. Is it hard? Yes. Is this attainable for most people? I’m willing to bet that it’s not. But you can try to do the very best you can. Start with your tax return and build from there. Pledge to yourself that this commitment will be worth it. Set up automatic transfers into your savings account so you don’t have to remember to do it.
  • Plant your seeds before you’re hungry. Okay, truth time. I worked incredibly hard in the two years before I got laid off because I essentially had three jobs: Mommy to two, PR professional in my full-time job, and YML as my part-time job. You will work harder for yourself than you ever will for anyone else so get used to that now. In the year before you branch out on your own, it will be a constant grind. And in that first year that you are on your own, it will be a constant grind. But you know what? Around year two, things start to gel a little bit. Your income stabilizes. You have a better sense of your hours and what it takes to run a business. And then it’s all gravy.

Sarah asks: How can you tell if a work-from-home job is a scam?

There are three things I look for to tell if a job is legit or a waste of your time.

  1. Misspellings. Most job postings are edited and refined so there shouldn’t be misspellings or typos.
  2. Contact information. If you can’t tell who you’re going to be working for, if there’s no website for the company or an employee that’s listed as a contact, I’d suggest you walk away. A reputable company doesn’t mind potential employees learning about them. They want you to visit their website, search their employees’ backgrounds, be knowledgeable about their product or services.
  3. Specificity in the job description. Let me give you an example: 

This is an example of a good work-from-home job ad. Why? It tells you exactly what it’s expecting and gives you examples of the type of work they are looking for.

You can look up their company, you can see the other websites they mention to get a feel for the style, you can assess if weekly articles are too much for you. They don’t mention payment in this ad, but you can look up Simply Good Media’s older job postings to see if you can get an idea of how much they pay for similar work.


  1. I think the biggest thing for me would be that it is scary. The unknown is scary. But seems you get more satisfaction out of it.

  2. Great tips and advice. As freelancers you really have to watch out for scams. I had a friend reply to a scam job post that requested a writing sample along with a resume and a few days later she saw her sample article on a website with someone else taking credit for it.

  3. It’s definitely incredibly hard to start from scratch as a freelancer. You don’t realize how hard it is to be motivated when you’re completely on your own…there’s no “to do” list unless you create it!

  4. This was a great article Tara, you made some great points. I can’t wait to read the rest of it. Maybe your next book should be about working from home, but based on how to do it, and how to budget for it, and how to prepare for it, etc. I work full time, am a mom, a student, and also took over my father’s home business. It’s all very much worth it though!

  5. Lisa James says:

    I am freelancing on oDesk and have faced some scams there. You have to be very conscious about them. Great and very valuable tips Tara !
    I am looking forward to your next posts and more success !

  6. Hi Tara:

    Great advice! I’d however add that traditional employment isn’t as secure as it appears. Increasingly people are losing their jobs or hours are being cut. What could be scarier than getting a notice on Friday not to come in to work on Monday? It can also take some people months to find another job; in the meantime bills are coming due.

    As a business coach, I know that starting a part-time business while employed is a way that many women transition into entrepreneurship. It also can be a cushion if a she loses her main gig.