Should I be investing my money more?

You came to the right guy! I know nothing

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Dear Shaun,

I know nothing about investing. I have a retirement plan that my job set up for me, but I don’t think about it. There are other people in my life that invest in the stock market and have portfolios and a money manager. Some people have brokers, some read about it and do it themselves. Any way you look at it, I feel left out. I feel like they are more stable than I am, and use that money for things that make them relaxed and happier. Should I be investing my money more? I feel like I barely have any to just exist, but should I use that minimal amount to try to score more?

-Investing Idiot

Dear Investing Idiot,

You came to the right guy! I know nothing either! I truly believe no one really knows what they are doing either. Million- and billion-dollar companies are always operating at a loss. The ultra rich are always claiming poverty on their taxes. Hell, even the somewhat rich are given extravagant lines of credit to keep up with their Lincoln car services and timeshares on an island south of here.

There must be a way to crack it, right? I look at it this way: I think I am doing a greater good to my family currently. I am building our own fence. Instead of hiring a company to install one for thousands upon thousands, I am building it myself with my own two hands. Is it taking me a lot longer to do? Yes. Do I have incredible blisters on my hands? Absolutely. Has the toddler now learned every curse word under the sun as he watches me rip rock after rock out of the godforsaken earth? Completely.

My fence is a little crooked, a little uneven, but despite it all, it doesn’t look half bad! It is sturdy and it is going to keep my son and two dogs in the yard, which is the goal. Does it have the professional look of a company who installs these in their sleep in just over eight hours? No. Did a crew of six put it together with the most accurate and top of the line tools? Certainly not. Does my son say “ah shit” when he spills apple juice now? You’re damn right.

By August I am going to have a fence. I’m going to be a little sore, the fence itself will look a little rough, but I will not have spent money, which in theory means that money is there for some other project, trip, or familial need. I totally could turn around and hand that money to an investment company to see if they can double that money. But they most likely are going to invest it in portfolios that include Exxon, Lockheed Martin, Monsanto, or Dow Chemical. How can I in good conscience give my hard-earned money to those ghouls? And hope they keep making bombs to turn a profit and give me my spending money for vacation? Not worth it.

What I’m telling you is to invest in yourself. That’s not some TikTok influencer bullshit either. Straight up just try to do it yourself. With the right preparation and planning you can get the things you need done, and keep your hard-earned cash in your pocket and not in the portfolio of some capitalist loser moron. They say fences don’t make good neighbors, but what if you invite that neighbor inside? Then you can show them your other portfolio: pictures you took of them behind your fence in secret as they sunbathed in the privacy of their own backyard.

Send any and all questions to woocomedyweek@gmail.com with the subject line "Bad Advice."

NEWS

I have a show this Saturday at City Winery in Boston. The room is pretty cool and the shows are always a fun time. If you’d like, you should come and check it. Tickets here.

On August 2nd, we have Ahmed Bharoocha (Conan). I started with Ahmed years ago and he’s been killing it out in LA for a while, so I’m personally very excited to have him back here.Get your tickets here.

ALSO, on August 16 we have a special crossover show where we are combining Hot Dog! and The Sort of Late Show. This is a special one to help kick off the Worcester Hot Dog Safari. There’s going to be some great gags and very fun surprises. You won’t want to miss it. Get tickets now!