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Posted by Nataly on August 14th, 2007

We have many moms on this site who are running their own businesses or are considering making the leap and doing it. Maybe you call yourself an entrepreneur, or a business owner, or a freelancer. Either way, you’re out there, creating your own work and doing it despite the many risks and challenges. This post is for you. I’ve recently published it over at the Huffington Post and it’s been fun reading through other entrepreneur reactions and comments. I hope that you will shares yours!

5 Dark Secrets of Entrepreneurship: What (Almost) No One Tells You About Starting Your Own Company

Before becoming an entrepreneur I worked with many of them closely for five years. I watched them start, grow, exit, ruin, and shut down their companies. You’d think there would be few things about starting a company that would surprise me. You would be wrong.

During my still-very-short tenure as an entrepreneur I’ve discovered many things that have surprised me. Here is my list of 5 Dark Secrets of Entrepreneurship. I’m sure it’s not exhaustive.

1. An entrepreneur, you feel stupid much more often than you feel smart.

Most entrepreneurs I’ve met in my time as a VC were really smart. Not all had good business ideas or solid management skills, but they were sharp. At the risk of sounding self-indulgent, I think of myself as a generally smart person. And yet, as I’ve been working on launching my company, I’ve felt dumb and stupid more often than I care to share. I’ve made bad decisions, wrong choices that in retrospect seem so easy to have been avoided, and I’ve learned a great deal about things I thought I already knew a lot about. Entrepreneurship is all about trying and building new things. Regardless of how smart you might be, doing something completely new and making endless mistakes can be stupefying.

(Now, I’m no Marc Andreessen and perhaps after a few billion dollar companies under my belt I’d feel less stupid starting my next one, but I’m not sure. Maybe I’ll email Marc to weigh in on this.)

2. Everyone is your greatest fan when you start, but support wears off quickly.

When I told friends and business contacts that I was starting my own company, the enthusiasm was overwhelming. It was like going from one cheer-on session to another, with tons of encouraging emails and calls sprinkled in between. It felt great and gave me a lot of confidence about what I was doing.

But this overwhelming support began to wear off as time went on. The big news about my new gig wasn’t news anymore and support quickly turned into feedback. Feedback is great — it’s useful and necessary. But it came in heavy non-stop doses. EVERYONE I knew wanted to give me tips on everything from what our website should look like to how I should word our email newsletters. Emails that began with: “Hi, I was just checking out your site and wanted to give you some advice,” became very frequent. I found myself with a strong urge for those great support-filled emails that flooded my inbox earlier on. As maybe too few entrepreneurs will tell you, we need as much cheerleading as we can get.

3. Regardless of your confidence level, you will often experience crises of confidence.

Most entrepreneurs I know are generally confident people. I don’t think it’s possible to take on the enormous amount of risk starting a company requires without being confident in your ability to overcome it. Apparently experts agree, which makes me even more confident in this assumption.

But being an entrepreneur involves consistently overcoming crises of confidence. You feel hopeless about making progress, you think your business is doomed, you think you’ve made the worst decisions ever. This is a crisis of confidence and you have to work very hard to overcome it. It’s a horrible feeling.

4. Nothing is ever right on the first try.

Your website design needs to be re-done. You hired the wrong sales guy. You strategy is wrong. Your name is spelled wrong on your newly ordered business cards.

Nothing works on the first try and regardless of how much you expect this, you feel crushed when it happens and you think you’ll get it right the second time around. Sometimes you do, but often you don’t. Our company is four months old and we’ve redesigned the homepage twice, modified our focus, changed many of our tactical feature implementations. Intellectually, I knew this is part of the process — everything is iterative and you learn only by doing. Emotionally this is rough because it often leads to #3.

5. You will take everything personally.

This morning an email came into the info box. It was from a woman who is married but chose not to have children. She spent three paragraphs writing about how prejudicial, judgmental, demeaning, biased, and damaging it was to create a site for professional moms (vs one for professional women). I read the email quickly and moved on to the next one. But it kept nagging me as I worked. I wanted to reply, to tell her the many reasons why I disagreed with her. I took it personally.

Now, some of you might want to dismiss this as a woman-thing, but don’t. I’ve now met enough entrepreneurs who say this is true — and they never admitted it to me until I became one of them.

What am I missing? Share your favorite dark secret of entrepreneurship in the comments.

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This entry was posted on Tuesday, August 14th, 2007 at 9:55 am and is filed under Entrepreneurship.

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8 Responses to “5 dark secrets about running your own business”

  • thisKat says:

    I’ve run a marketing design company for 6 years. I think all you’ve said is true, though I personally found the cheerleading to be non-stop. I think Portland is an entrepreneur’s Eden.

    One thing that I discovered, and this is particularly pertinent to moms, is that running your own business does not neccesarily give you the flexibility in your schedule you may have envisioned. I worked 50+ hours a week for the first 2 years of my first daughter’s life. This didn’t work for me. Yet, by the time I’d had it, I had a strong client list and reputation so I could change my company to one with a downtown office with 8 employees to a home-based consultancy with contractors. I still have to put in a solid 20 hours a week–and don’t forget sales time!–but I finally have some breathing room. Still, without those first 5 years of hard, hard work this wouldn’t have been possible. If I’d tried to *start* this business at home, with contractors, with kids, it would not have grown as quickly as it did and I would not be able to command the rate I can or attract the caliber of clients I have. And I do have to have a part-time nanny for my toddler, and preschool half-time for my now three-year-old, in order to have enough availability for clients.

    So while some may pity the “corporate slave” know that there are many sacrifices and trade-offs when you are the one and only boss and nothing happens without you setting it in motion.



    I completely agree about flexibility - I was talking to someone today and said that when I quit my venture job I was looking for a more flexible job. This is the hardest job I’ve ever had:) But I do choose the 80 hours a week that I work - which has allowed me, for example, to take off Friday afternoons to be with my daughter. (I usually work late into the night to make up for things like that.)

    Oh, and I checked out your blog and plan to make the raspberry muffins this weekend!
    -Nataly

  • Annemarie says:

    Hi Nataly,

    Just for the record…
    I think what you are doing at workitmom.com is
    ASTOUNDING!
    EXCITING!
    REVOLUTIONARY!
    NEEDED!
    GIVING WORKING MOMS VOICE!
    SHATTERING THE ALONE FEELINGS SOME MOMS FEEL!
    HELPING MOMS GROW!
    SHARING YOUR EXAMPLE & INSIGHT!
    LINKING ARMS WITH WORKING MOMS ACROSS BOUNDARIES!
    BRILLIANT!
    :)

    When I joined workitmom.com and saw how easy it was to network (everybody is so friendly & doing amazing things!) I felt at home really fast. I read over the supportive blogs/ comments that are packed with great info. I can use to expand my business. It was like finding a home online and I am sooo grateful for your efforts, and all the workitmom.com moms!

    About having my own business & sharing the same 5 secrets?
    YOU BET!
    The trick is to keep it FUN and ENJOY the process.
    My work as a life coach means I get to help women with this all the time.
    One reason I loooove my job so much is that it is about finding the enjoying!

    I think having your own business as a mom is one of the real daring tests of life
    that would give contestants on “Fear Factor” a run for the money :)
    and I love it!!

    Thanks for sharing, Nataly.
    Knowing the 5 secrets aren’t really secret makes them less dark!

    Talk to you soon,
    Annemarie

    —–
    Annemarie, can I come through your computer and hug you, right this very minute?
    If I said it means so much to hear from an actual member that what we’re building here is valuable means a lot I’d be lying. It means EVERYTHING.

    -Nataly

  • Florinda says:

    One of my articles for this very website concerned the tangible and intangible benefits of working for someone else - not everyone’s made for entrepreneurship, and I’m pretty sure that includes me. But you Work It, Mom! members who are running your own businesses - and your families - have my respect, support, and many cheers! :-)

    Nataly, I’m echoing Annemarie and probably speaking for many other members when I say that I’m glad you took the plunge into this, and thanks for all you’ve shared with us along the way!


    Florinda, thank you! And oh, how I miss some of the intangible and some very tangible benefits of working for someone else! (My boss… hmm, me, refuses to give me a day off. Period.:)

  • Anonymous says:

    5 Dark Secrets About Running Your Own Business…

    These are the things nobody warns you about starting your own business……

  • Jen Creer says:

    People will avoid talking to you or asking you how your business is doing because they secretly think you have failed. LOL. At least, that is true in my case. Or they don’t think I could possibly be making any money. They say, “Are you still doing your online stuff?” and the way they say “stuff” makes it sound like they think I am bending pipecleaners into little action figures or something like that, rather than actually working.

    It doesn’t bother me, though, because I know the truth. I enjoy watching them squirm. My inside joke, because I often take my laptop out of the house, is that I “work” at the coffee shop. I can’t tell you how many people automatically assume that I will be making their lattes.

    I have done the business card snafu. Argh!


    Oh, you made me laugh - it’s similar to when people say “Are you still doing that mommy site?” :)
    Nataly

  • Heidi Richards says:

    Many thanks for excellent topic - 5 dark secrets about running your own business. And I wanted to add that it does not matter how long you have been in business, these issues keep popping up from time to time. And just when you think you’ve got the world by the tail, the universe shifts and you are back at square one, two or three!

    I have been in the floral business for 26 years and started an Internet based membership organization in 2003 because of all the changes I have seen in retail. Take the price of gas for instance. Who would have thought that in the US gas would have such an impact on the price of flowers. Well flowers are shipped via air cargo and so when gas went up, so did shipping costs and the price of flowers have been higher since, with no signs of coming down to where they were even a year ago. They have risen well above inflation rates for the past few months.

    The WECAI Network™ to which I referred is doing great - we have 1200 members representing 54 countries and growing steadily each day - even with all the competition out there. Because the key to success in any business is differentiation. And that is why so many businesses fail, they are no different than the “shop down the street” or the “website next door.”

    keep up the great work. I plan to stop by and say Hi from time to time and will also include your blog in my top 5 women who blog list - I post each week.

    Wishing you all the best… and more!

    Heidi

    Heidi Richards, Founder & CEO
    http://www.WECAI.org - “Helping Women Do Business on and off the WEB™”
    http://www.EdenFlorist.com - “NO Reason is the BEST Reason to Send Flowers!
    Be sure to check out the Women’s Writing & Publishing Summit that took place Online July 19-21 & 25- If you were unable to attend, you can still purchase access to all 15 sessions at http://www.womenswritingandpublishingsummit.com


    Thanks for stopping by, Heidi - and yes, being different from competition is so critical for a small business!
    Nataly

  • Meri says:

    Hi Nataly-

    I couldn’t agree more! I actually didn’t have alot of cheerleading when I ventured into my own business. I had a lot of nay sayers from the beginning. I think the part about taking things too personally is so true and often leads right into that crisis of confidence. It can stop you in your tracks if you let it.

    I am truly amazed at what you have accomplished in 4 months- your business is growing fast and I know how much effort this has taken as a fellow online business owner. You have created a wonderful, supportive environment for working moms. And just as a side note…I am an entrepreneur with no children (yet!) and do not find it demeaning or biased in the least. A matter of fact…I am learning alot on how to get prepared for running my business when I do have children. Thanks for all your hard work! :)

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