Starting A Business Is Like Asking Out A Girl For The First Time

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Perhaps it’s due to the bad economy, but many of my friends lately have become increasingly frustrated with their day jobs. Taking an informal poll, over 80% of them would much rather be working for themselves than for their current employers. Of these 80%, many of them are staying at their current positions because they are grateful just to have a job in this down economy.

As a result of their frustrations, more and more of my friends have been asking me about the details of our online business and how we found the courage and knowledge to begin. What did it feel like when you first opened up your store? How did you come up with the idea? What made you decide to act on it?


Photo By Martin

I’ve answered so many of these questions recently that I’ve decided to write this article with the best analogy I could come up with. Starting your own business is like asking out a girl for the first time.

How I Met My Wife

I distinctly remember the first time I saw my wife at the A+J restaurant in Cupertino village. My buddy Y and I stopped in to grab a bite to eat when we saw our mutual friend V dining with a group of her friends. I remember taking turns saying hi to everyone at the table when I became suddenly overwhelmed by the beauty of this one particular girl whom I’d never seen before.

Her cuteness struck me so hard that I was speechless and for some strange reason, I couldn’t look her directly in the eye. In fact I was so out of it, that I forgot to introduce myself and didn’t even get her name.

Later that evening, we all went out to a movie together as a group but I couldn’t really speak to her all that much. I was struck by shyness and my tongue wouldn’t work properly. Worse yet, the night ended and I didn’t even get her number.

A Lost Opportunity Due To Fear

Looking back, not getting my wife’s number that night was potentially one of the biggest mistakes of my life. I was too scared to act and I blew a huge opportunity. What if I never got to see her again? What if she wasn’t single the next time I did get to see her?

This is the exact same way I felt when my wife and I first thought about starting our business. Basically, we hesitated. Deep in our hearts, we wanted to start something but we were scared because we knew nothing.

We knew nothing about creating websites. We knew nothing about all of the logistics and legal aspects of opening a store. We had no clue what we were doing and so we did nothing for a very long time.

Now that we run a successful business, we regret not having started earlier. We should have pursued our ideas long ago. When I first met my wife, I should have followed my gut and asked for her number without hesitation.

What If I Get Rejected?

Should’ve could’ve would’ve. Acting on your gut is easier said than done. Truth is, I didn’t ask out my wife that night because I was afraid of getting shafted. I was afraid that if I got rejected, that my friends would gossip about me.

“Man, that Steve has no game. Did you hear he got dissed by Jen? Ouch!”

Where I live, my community and my circle of friends are extremely tight. Word travels fast. If I got rejected, all of my friends would’ve found out pretty quickly.

The same was true for our business. My wife and I weren’t afraid of losing money per se because our business didn’t cost that much to start. But we were afraid of losing our dignity and our confidence. What if we wasted months of our time on a business that never made any money? What if we discovered that we were incompetent? What would our friends think of us?

Another Botched Attempt

We all get scared of taking chances in the beginning. But once you get over your initial fears, you’ll feel exhilarated. You’ll feel alive. You’ll get swept away and your heart will beat at a million beats per minute.

I got another chance to ask out my wife at an engagement party several months later. I remember seeing her at the party out of the corner of my eye and feeling absolutely euphoric. I felt quivers in my stomach and my palms were sweaty but dammit! I told myself that I wasn’t leaving the party without making an attempt at getting her contact information.

Me: Hi there!
Jen: Hi. I’m sorry what as your name again?
Me: (Ouch! I guess I wasn’t that memorable) I’m Steve. Remember we went to see Eyes Wide Shut a couple of months ago?
Jen: Oh yeah! How are you doing?
Me: Good. You know we work pretty close to each other. I was wondering if I could get your business card. Perhaps we can have lunch sometime.
Jen: Sorry I don’t have any business cards on me. But…
Obnoxious Friend: (**Rudely Cuts Jen Off**) Don’t mean to interrupt. Can I borrow Jen for a sec to help me with the dessert?

I was dumbfounded. What was Jen going to say after the BUT?!?!?! Was she going to give me her number? Why didn’t she finish her sentence!?!?! Unfortunately, she was abruptly whisked away thus ending our conversation and my hopes of getting her number. I had failed to obtain the digits for the second straight time.


I remember leaving that engagement party feeling extremely dejected. How did I screw it up again? How hard was it to get a frickin phone number? Perhaps it wasn’t meant to be.

Dejected is something you will probably feel at some point with your business and you will need to dig deep to get out of your rut. After the engagement party, I felt sorry for myself for a few days and finally got fed up with myself.

Screw it! I’m just going to ask my friend for her info and I’m going to call her out of the blue. I don’t care if everyone knows that I’m going to ask her out. I don’t care about getting rejected! And so I found her number and I asked her out the very next night. The rest is history.

Why Not Take The Chance?

When it comes to starting your own business and initiating relationships, the rewards always outweigh the risks. If I never asked out my wife, I wouldn’t have my family today. I wouldn’t have a loving wife and a cute little daughter to play with.

If we didn’t have our business, my wife wouldn’t have the pleasure of quitting her job to raise our daughter. The truth is that our lives would not be the same had we not acted on our desires.

Do you want to live your life regretting what you could’ve done? There comes a time when you just have to stop caring what other people think and just act on it. Take a chance and you’ll be pleasantly surprised.

Ready To Get Serious About Starting An Online Business?

If you are really considering starting your own online business, then you have to check out my free mini course on How To Create A Niche Online Store In 5 Easy Steps.

In this 6 day mini course, I reveal the steps that my wife and I took to earn 100 thousand dollars in the span of just a year. Best of all, it's absolutely free!

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32 thoughts on “Starting A Business Is Like Asking Out A Girl For The First Time”

  1. Great story and lesson for all of us! Right now with my business, I do question some of the choices I made over the past few months, but just like in a relationship, I am able to solve some of these issues with patience and persistence. You never know what would happen if you didn’t try!

    1. Hey Carla,
      Nobody ever accused of you of not trying:) It must be tough battling illness while running a business at the same time. Good luck and I hope everything works out.

  2. What a great story and a great analogy! Taking the plunge is always so difficult. One possibly good thing about all the layoffs is that they are pushing people over the edge and forcing them to re-think what they want to do with their lives. I’ll bet, when it’s all over, there will be lots of people saying that getting laid off was the best thing that ever happened to them because it forced them to start their own business and now they are happy. At least I hope so!

    1. Hi SimplyForties,
      I think you are absolutely right. This downturn has caused people to reflect on their lives to reevaluate what is truly important. Hopefully when all is said and done, people will take action and pursue what they dream of doing.

  3. Fantastic reading. I love the analogy. I started my own business 10 years ago but you still made me feel like in my early years. Yes, acting on your desires with courage and confidence is exhilarating. And the reward is deep and long lasting.

    Thanks for a nice post :-)

    1. Thanks Dragos!
      I really appreciate you supporting the blog with your comments. With the biggest risks come the greatest rewards and yes, they do last a long time.

  4. Great analogy. When I met my current girlfriend on a blind date she was a total b***ch and I left the restaurant thinking “no way in hell am I calling her back”. She took the initiative and called me later in the week and offered to come make me dinner to make up for her mood and we’ve been together going on 4 years now (I have commitment issues, maybe she’ll propose.). Sometimes it feels like business is the same way. Being a developer I get handed ideas left and right and it’s just a matter of getting off my butt and doing something about it.

    1. Hey Jace,

      That is hilarious. I guess your woman figured out her mistake and made up for it. That’s a pretty cool story and congrats on having a wonderful 4 years. You’re right. Hardest part is gathering the courage and everything is downhill from there. Thanks for the comment!

  5. Love it!

    We are currently in the “another botched attempt” stage with our business. Hopefully nothing is botched at this point but we are sitting around with our motors running waiting for a green light.

    It’s frustrating!

    1. Hey Ashley,
      I just read your latest blog entry. What exactly is your business? It sounds like some sort of temp agency but I couldn’t figure out all of the details from your post. In any case, it sounds like you have a great opportunity on your hands and congrats for pursuing it! Good luck with everything.

  6. Thanks for the touching story about you and your wife.

    I realized something while reading your story… I’ve been interested for some time in starting my own venture, but I truly felt I had no idea what to do. No great idea hit me in the head one day, the kind of “AHA! I’ve Got A Great Idea!’ experience, so I go through every day thinking, well, with no great passion or idea to grab me, how on earth could I even dream of doing something on my own ? So nothing happens.

    What I realized when reading your story is that my lack of a great idea is just a symptom of how I interact in the world. With no great passion about myself or what I do, always seeking to stay under the radar, do a good job but not stick my neck out, always trying to keep to the status quo… that this is why not much has moved in my life in a long time. Including why I am still doing the same job I did 12 years ago.

    Sometimes doing the same job is not a bad thing (UI suppose we cold ask some laid off auto workers about that). But… plenty of But… Being in the high tech industry, and working all the time with new technology… and having at least the inclination to do something more… then sticking to the tried and true doesn’t cut it for long.

    So, thank you for your story. Funny how what one writes sometimes elicits something very unexpected in others.

    There’s more work on myself I need to do.

    Thank you again.

    1. Hey Seeking Lemonade,

      I’m glad that this post had an effect on you. I felt the same way as you for many years but the good thing is that it is never too late. I wish you the best of luck on your future changes.

  7. Very nice article on boosting sales.
    You have clearly explained just a start on everything does half of the thing.
    Yes as u said the past reputtions speaks a lot.We need to forget all the negatives and keep remembering all our accomplishments to motive ourselves. So in tamil there is a saying “vallavanukku pullum ayudham” it means for a man who acts in an intelectual way even a small grass serves as a weapon.
    I have summarised some nice practices from my experience and im sure it really helps u out with ur business.

    1. Hi Sandeep,

      For some reason the link you posted got cut off. Please send it over again when you get the chance.

  8. Awesome, a love the story- it helps to get your point clearly across. :) Thanks for sharing. I should share how I met my fiance at Simply Blog.


    1. Hey Miguel,

      Whenever you have that post up, let me know. I want to check it out.

  9. A happy marriage as well as a happy business, eh? You know your mistake at the second party was to ask for her number. You should have given her an opportunity to ask for yours – she sounds a prize and doubtless gets asked out all the time, so you need to be a bit different (which you’ve obviously turned out to be! :) )

    Not sure what the business analogy for that freebie dating tip is! Maybe make sure you give opportunities for your customers to make the first move? Erm…

    Keep up the great blog.

    1. Hey Monevator,

      My wife and I just talked about your comment. If I waited for her to ask for my number, I’d still be single today. She has never asked for anyones number ever:)

  10. This morale of this story applies to so many things in life. From starting a business to writing, the hardest step is the first one. Thanks for the encouragement!

    1. @Sandra @Jolina

      Glad you both stopped on by. Thanks for reading!

  11. Great…. sometime we scare of something because of our fear of losing.

    Thanks great post.

    We cannot get the distance without a risk…

  12. Its my pleasure Steve your post is very nice to read. And readers can get inspiration, lessons in life.

    much care


  13. I so love this post! I really can identify with it. I am in the midst of taking a chance on a possible new business idea and I just have to say, the way you put it in this post simply is encouraging. God bless you.

  14. Jonna says:

    This post has struck my senses. Very encouraging indeed. Guess what, I was one of those unfortunate who have been retrenched. I never really know what retrenchment means until Friday de 13 (of last month). Lucky number right? Anyway, even before this saddening news hit me, I’ve been crying for no reasons the moment I get up from my bed just to go to work. And when I assess the situation, I’ve learned that I hate going to work anymore. All I wanted is to be at home and do my business there. Without a boss to tell me what to do and cram when clients dictate what shall I do next. It’s tiring and worst, I’m not really happy anymore and stresses me to death. Instead of mourning that I loss my job, I’ve celebrated it by watching DVD all night, reading blogs, doing the household and pray hard. I guess I was too afraid to take chances. But not now, I’m more than willing to take chances and all set to follow what my heart truly desires. I’ve got to thank others out there for inspiring me (and that includes you). I really hope that my business venture will work out fine.

  15. Frank says:

    Hi Steve,

    Very interesting story! :-)

    How much capital did you set aside when starting your ecommerce business?

    Also, did you ever ask Jen how she felt when you suddenly called her out of the blue? I hope she didn’t think you were a creepy stalker? =P

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