Single Mom Bootstrapping with back against the wall

I am a single mother with a teenage daughter heading to college. I live from paycheck to paycheck and I am bootstrapping a start up with any spare money that I may have. I am in credit card debt, my time is at a premium and I work full time in the construction industry in a mid-level staff position.

I am scared. I am scatterbrained and drained.

I cannot give up my day job because it pays the bills, but each day I dream of walking away. I am afraid to ask for credit for fear of raking in more debt, so I work at a snails pace by self-funding.

How do I get over this massive fear of failure that is suddenly looming over my head? This is my dream and now I am overcome with fear with so many odds against me. How did you get over the hump if you were in a remotely similar or familiar situation?


  • You are not unusual. If you have a reasonable amount of market research that supports your idea, have confidence that you will ultimately reach your goal but not as fast you would like.
    Remind yourself of the success you have had with raising your daughter. Now, imagine that you will have to do it all again — but with your idea for a business. Entrepreneurship can be a tough and lonely job. Try to compartmentalize what you have to do for your idea into the hours you have available while leaving a bit of time for “social” to keep your “sanity”. Hopefully, you have a good friend to talk with to help relieve the stress.

  • Watch the two videos on TWIST ( this week in startups) on you tube. The two interviews are with Jerry Colonna a famous VC, now a life coach. These interviews should help clear your head and set things in perspective.

  • Kind of in a similar spot: four kids, a side business and a day job I can’t leave. Married. That gut wrenching fear of failure has definitely been a huge drag that’s taken years for me to get to quiet down. How am I getting over it? Don’t know if I really have but trying to put less pressure on myself to succeed. It’s not life or death. I’d love to be able to get to the point I can leave the day job but if it doesn’t happen at least I’ve tried. My disgust with worrying is just starting to outweigh my fear of failure. I’m sure it’s different for everybody though – hang in there.

  • You’re amazing, you embody the true qualities of a real entrepreneur. You are the type of person who has a story behind you, you will stand out among others because of the tough situation you’re in. Believe me, when you get going (and you WILL), this will be your story of how you overcome odds to make something happen. This will be valuable to you when you need to convince investors (or early adopters of your product/service) to believe in you.
    I am struggling to get businesses to signup for my product, I left my job to focus entirely on it.. I promised my wife (and baby on the way) that I would make $100k+ by mid this year… so I have a time limit over my head. It is stressful but it forces me to plan. Have you tried setting time goals for yourself? If you can’t achieve X by Y, then you’ll shelve the plan temporarily and try to get a promotion at your full time job.. or try to get another job.
    Best of luck to you.,

  • Try finding someone else to become a cofounder or maybe more than one or two. Share the work, share the dream, share the investment. One is the loneliest number you will ever know. Ok, so an old song, but very true. The likelihood of one person having the knowledge, the time, and the money to create anything if value us slim to none. There is power in numbers. Best of luck.

    Do not accept failure under any circumstances. Many times people get close. Many times people get in a box and can’t see that maybe the idea needs to be tweaked. Ask questions, move mountains, get people involved. LEVERAGE is the most important word you can know in business.

    Best of luck.

  • I went from being homeless and taking public showers once every few weeks to learning how to code and launching a startup. I come from a single parent household so I understand the hardship and I started building our business the same way – bootstrapped with other client work.

    Realize that it’s going to take a while for you to build your business. Give yourself a break. Don’t expect or plan on a three month ideation to successful launch cycle. Release something small and then step back and track the data for a few months. You’ll have a huge advantage in being able to learn what truly works & what doesn’t. We worked for three years and multiple versions around a core concept that I’m passionate about. Each version gets better, and each has moved us closer to where we want to be. We’re not there yet, but we know more about our industry than anyone.

    Also, see if you can find some entrepreneur groups in your area. I’m part of one and am amazed that everyone – literally everyone – is in the same boat you’re in. Just because you see huge launch parties & beautiful apps & offices & employees doesn’t mean their not as freaked out, scared and drained as you are. You’re in great company 🙂

  • There are a lot of resources for women – here is a great article http://newsroom.cisco.com/feature-content?type=webcontent&articleId=1404296

    I have a different opinion from others here… startups are an enormous risk and you should try to minimize your risk as much as possible. Find an investor as soon as possible, work on your pitch deck and marketing and don’t dig a hole for yourself.

    Sad but true- women get 4% of venture funds. That means that men get 96% of the money and they are often younger with more “bandwidth” to couch surf or go live in an incubator.

    Don’t take on any risk, or any debt that you can’t afford to lose.

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