When I was 27 the startup I worked for brought in a “financial advisor” to meet with employees. A bunch of tech 20 somethings in flip-flops and shorts sat in a conference room with this suit for 15 minutes each so he could guide us on our 401K contributions.
His disposition made me feel like a kid who had forgotten to hand in his homework. The way he reacted to my questions made it seem like I was asking him about the long-term earning potential for my stockpile of magic beans.
Clearly, my investment strategy was lacking.
I hadn’t anticipated being so embarrassed. I readily agreed to his recommendations without thinking so I could flee the room before the heat rash working its way up my neck caused my head to burst into flames.
I’m almost positive I didn’t do what he told me to.
Not long after that exchange, I was at a work happy hour. One colleague, the same age as me, was talking with his girlfriend about their investment portfolio. Again, a private flush hid beneath my clothes. I felt smaller. Younger. Speechless.
I felt ashamed I had no real investments to speak of. I had my apartment which I bought the year the housing market collapsed and a couple of IRAs that if worse came to worse I could live off for a full three months. I went from blissfully unaware to very clearly behind. But I still had time… right?
Today, eight years later, I’m still wondering if I have time.
Because shortly thereafter I left that startup and cashed in all my stock to start my own business. Some people left their stock untouched, others used it to buy vacations or homes. I used it to buy my freedom from an office.
I figured I could afford to live for a year on that money if I didn’t sign any clients. And damned if that was just about what happened. I had no idea how hard starting a business would be. I was optimistic and ambitious. I thought I would do whatever necessary to succeed on my own. And I did, but it still meant many lean months.
Every year as I hustled and struggled for clients I would tell myself I was investing every dollar I made into myself, growing not just a business, but a life. Eventually, all my efforts would pay off in spades. I would establish regularity, momentum, and ultimately earnings. I pictured those toy cars you pull back that shoot forward once you release them. I was just pulling back a lot.
But my car never shot forward.
I’d sign a client, save some money, have a dry spell, and plunder my savings to get through the following months. It is easy to find articles about how to plan for irregular income. They all say the same thing: Have a rainy day fund, know the minimum amount you need to get by. But those articles don’t say what to do when the money runs out and there is none coming in.
Investing was the furthest thing from my mind when all I could think about was paying my credit card bills. I was not at all prepared for the wild swings in prosperity. As the size of my projects grew so did my highs and lows. A single client might sustain me for half a year, but I could also go just as long without getting a check.
Feast and famine. Leaping forward and sliding backward. All with the hopes the leaps would be a little bit greater and the slides a little less frequent.
Meanwhile my “investment portfolio” sat lonely on the internet. A soccer ball I played with for a week and then left outside to weather the seasons. Just another indicator that I was not “on pace.”
Mint.com sent me monthly notifications to invest in my retirement. I turned them off.
And now at 35, I wonder what next? How do I get back on track, live the life I want and still plan for the future? Is it even possible? It is the dichotomy I always feel. The desire for security but the need for the non-traditional. I want an upward trajectory, but the path I choose often meanders, twirls and loops back on itself.
Lifestyle design by Harold’s Purple Crayon.
It was for all these reasons and more my fiance and I recently met with a financial advisor. While it wasn’t as embarrassing as it was eight years ago, it was no less difficult. He asked us questions we had almost no ability to answer. I thought meeting with him would promote clarity and enable confidence in our decisions.
Quite the opposite.
Those TV commercials where kindly looking older men ask the viewer to predict their retirement made the conversation seem so simple. We were asked about scenarios we hadn’t discussed. Kids. Vacation plans. Homes. Questions I had hoped to answer with my purple crayon now demanded incredibly specific numbers for a spreadsheet.
All I wanted to say was; “you tell me.”
We walked away with a bunch of target numbers we knew we wouldn’t be able to hit. We undertook the exercise with the hope of getting ahead but it just made us feel more behind.
This is the part of the piece where I share with you how we got caught up on our savings and stopped worrying. Except that hasn’t happened yet. There is still a lot of private shame and embarrassment I feel when it comes to retirement savings. All of the numbers and estimates make it seem like retirement one day is more of a wish than a reality.
I’m not sure those fears or anxieties ever go away. All we can do is try to make smarter decisions. Save a bit more when we can. Spend a little bit less. It is a constant negotiation between the life I want and the life I need.
Perhaps my little car is still being pulled back, ready to shoot forward on a track drawn in purple crayon. Onward. To a spreadsheet.
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