investing virginity

I’m losing my Investing Virginity. Are you with me? #InvestNow

Here’s something I never thought I’d admit publicly on a blog: I’m a virgin.

I’ve gotten pretty far (maybe third base), but I’ve never gone all the way. I’ve been close – really close – but I couldn’t get up the courage to make the first move. It just all seemed too risky. Too many unknowns, too many ways to get hurt.

But this year feels different. I’m ready.

It’s time I finally lost my investing virginity.

I’m not completely inexperienced, but I’m scarred from my first time.

Okay, so technically I’m not a complete virgin. I’ve had a few flings in the investing space:

  • My slow-n-steady retirement savings: Since I entered the workforce a few years ago, I’ve contributed a good amount toward my retirement (I’ve got both a Roth IRA and an IRA). As a young professional in my twenties, I’m pretty proud of where I’m at and a big believer that saving in a 401(k) is an easy way to get introduced to investing. But I wouldn’t consider that really losing my investing V-card. It’s the equivalent of “third base,” and I want to take the plunge into investing outside of my retirement.
  • My terrible experience buying an individual stock right before the market crash: Oof. Talk about a terrible one-night stand. I decided the first time I would buy stock in a company would be when prices were dirt cheap – and that happened to be right before the 2008 market crash. I took $1,000 out of savings and put it into my favorite bank that was selling really low: Washington Mutual. Fast forward four weeks and Washington Mutual no longer exists, I’m out $1,000 and I have made a bow never again to dabble in the stock market until I knew what I was doing. (You can read more about my terrible $1,000 mistake here.)

So I’ve been hurt. And yes, I’ve dipped my toe into the investment water with my retirement savings. I suppose all this makes me a born again investing virgin. 🙂

But regardless of my past, I want to go all the way this time.

I just need to stop being so damn scared.

Scared of investing

Despite having plenty of information at my fingertips, I’m still scared that I don’t know enough. The crazy part? I help people understand personal finance for a living… and I haven’t gotten up the guts to do it myself. Heck, I even posted last year that I was ready to make a move – and I still didn’t do anything about it!

But I can’t delay this anymore, especially now that I’m debt free. Paying down my student loans meant I was boosting my net worth with every monthly payment. I was reducing my debt, which meant less interest to pay in the long run. So now that I’ve crushed my student loan debt, I need to be just as aggressive in growing my net worth. And boosting my savings just isn’t cutting it.

Stop being scared of the worst case scenario

Just what exactly is stopping me? It took me awhile to peel back the layers of my investment fears and I realized that I had been imagining the worst case scenario: losing all my hard-earned money again because I made a bad choice.

So I decided to break down my fears and the worst case scenarios:

  1. What’s the worst that could happen if I started investing? I could lose some money. I could lose $1,000 again. That stunk when that happened last time. But I won’t be investing in individual stocks again. So maybe the worst case scenario won’t be that bad.
  2. What’s the worst that could happen if I did nothing? I could actually lose more money by not acting. Sure, I could still save money in a bank, but it wouldn’t be growing. I wouldn’t be putting my money to work for me. In fact, by not doing anything, I could lose out on tens of thousands of dollars. OUCH.

investing virginity

Your worst case investment scenario? You could lose tens of thousands of dollars…by never starting.

I may lose money initially. But I won’t gain a thing if I never start.

Okay, that’s it. And now I’m finally ready to start. I just need to take a big breathe and make the leap 🙂

How I Plan to Lose My Investing Virginity

Over the next few months, I’m going to walk through the step-by-step of how I’m going to lose my investing virginity: where I’m investing, how I’m setting up my accounts – an open kimono. In case you’re wondering, here are the options I’m considering:

  1. Invest in a Vanguard S&P 500 Index Fund: This is hands-down the most recommended investment product out there (and by most recommended, I mean by the blogs I read and my friends that are investing). It seems well-balanced with low fees. I’ll take a look at it in more details in later posts.
  2. Invest using Betterment: Betterment is an ultra-simple do-it-yourself investment tool with a sleek, easy-to-understand interface. It takes a few minutes to get up and running and seems like another great option for beginning investors. I’ll investigate further in a later post.

Ready to lose your investing virginity, too? Stay tuned for more posts to come. Now that I have a plan,  I’m hoping to have lost my investment V-card by next month. Wish me luck 🙂


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14 thoughts on “I’m losing my Investing Virginity. Are you with me? #InvestNow

  1. Brad Young

    Excited to follow your journey!

    When I started with my current company (2 yrs ago) I opted in 8% of my paycheck to ESPP. Only 5% discount per stock but has risen from 65 to 110 since I came on board. I’ve felt a little nervous about venturing outside of my corporate comfort zone though 🙁

    1. Stephanie Halligan Post author

      I hear ya, Brad. We’re going to break through those comfort barriers and do this together! 🙂

  2. Erin @ My Alternate Life

    I can’t wait to lose my investing V-card! I do save for retirement in a Betterment IRA and that makes my life really easy, but I’d love to invest outside my retirement savings.

    Good luck! Can’t wait to see how it goes 🙂

  3. Valerie Rind

    Stephanie, I wish you all the best on your journey!

    I read a theory recently about the psychology of investing (there are TONS of books and articles on that subject). When we gain, we chalk it up to our being smart and making good, informed choices. When we lose, it’s always because we had bad luck or it was the market’s “fault.” Something to keep in mind!

  4. Cory B.

    Hey Steph!

    I feel very fortunate that my father set me up with several investments since I was 5 and opened my first bank account. I’m excited to hear more your adventure!

    Here’s a question that I just had: I recently opened up a$5000 line of credit with my credit union. The original intent was to have to a) improve my credit score, and b) have it as insurance in case I get into an accident and have to cover hospital bills. With an interest rate of 6.25% per annum, should I invest it into something more profitable?


    1. Stephanie Halligan Post author

      Cory, awesome to hear you had a great head start! Sounds like you opened a line of credit but you won’t be carrying a balance on it? Of acts the case, you have nothing to worry about. Or if it’s a CD-type product, that’s a kick ass interest rate!!! I want to sign up with your credit union 🙂

  5. [email protected]

    I lost my investing v card years ago. Fortunately I wasn’t too scarred from the experience to stay in the game. I do focus on investing for retirement but I’ve also found some non traditional ways to invest. I’m in partnership with someone I know buying and reselling old go-karts and atv’s. It is a little unorthodox but there is certainly money in it. A bad experience isn’t a reason to stay out of the game.

  6. B.

    Hi there! I know I’m super late to the party, but it’s AWESOME that you’re taking the plunge! I’m still working on getting debt free, but by the end of the year I’m looking at having enough saved on the side to open an IRA account in time for my next birthday. A lot of people tell me I should invest first (and I understand the math of making your money work for you) but I need the mental peace of mind knowing I don’t have student loans on top of that. Plus, I’m a terrible multi-tasker haha!

    Keep us all posted on your investment journey!

    1. Stephanie Halligan Post author

      I hear ya! It’s a tough balance. Piece of mind and less stress vs. a return on investment is a hard choice to make. It’s totally up to you, but it doesn’t hurt to get started, even just a little!


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