The Uncertainty of Politics — and Its Affect on Small Business Investors

I come up with a new goal and a business plan to go with it — and realize that this simply isn’t a good time to take risks.

If you’ve been following this blog for a while, you should know a little about me, but if you don’t, let me fill you in on what’s important to know for this post.

At Chicago
I crossed my wake in Chicago on August 12, 2024. Here’s my boat, Do It Now, in a slip at DuSable Marina in Chicago, exactly 6 feet away from the slip I started from in October 2022.

I’m currently 60-something. I retired from my most recent career as a helicopter pilot in 2023, after selling the helicopter, the charter company, and the cherry drying company in 2022 and 2023. I took the proceeds from those sales and used them to buy a 32-foot “pocket yacht,” which I shipped to Chicago in October 2022. I then spent most of the next two years cruising on that boat, alone and with friends, along the Great Loop. (I blog about that in my Great Loop blog, so if you’re interested, please check it out.)

Big Garage
The bigger your garage is, the more stuff you’ll accumulate to fill it.

I finished my Great Loop trip in August 2024 and trailered the boat back to the Seattle area, where I launched it in Puget sound. I then spent most of the next month cruising around there and the Inside Passage before bringing it home and cramming it into my very large garage for the winter.

In those final days on the Loop — keeping in mind that I covered more than 8,000 miles — I realized that the part of the Loop I liked the best was the northern part, say from New York City all the way up to Canada and then west into the Great Lakes. There’s nothing quite like cruising in the lakes, rivers, and canals of New York and Ontario; I felt that I could do it forever.

At Valcour Island
Here’s Do It Now anchored off Valcour Island in Lake Champlain in June 2024. I could spend a lifetime exploring the waterways of New York and Ontario.

Wouldn’t it be great to do it every summer until my age caught up with me and I was done boating?

Goals

I’m a person of personal goals and finishing the Great Loop left me kind of floundering without one. I also felt weird about being retired — not having anything to do to bring in a few bucks to cover my living expenses. I was living off my retirement savings, waiting a few more years to start collecting social security, and it didn’t look as if running out of money was going to be a problem. (I’m remarkably thrifty about some things.) Although my side gig as a silversmith did bring in some money, it was small change without the potential to get much bigger — unless I was willing to spend five days a week in my studio producing jewelry and a bunch of time finding new markets for my work. I wasn’t.

But when I finished the Loop I felt the inklings of a new goal coming on, a new business endeavor where I could spend eight months of the year cruising northern inland waters and the remaining four months soaking up the sun in Arizona. I’d use my captain’s license to offer one- and two-week cruises to a specific potential market of people, cruising in the waters I wanted to explore while teaching them what I knew about cruising. The money I brought in would cover my cruising expenses, reducing my cost of living and helping me preserve some of those retirement savings.

I’m Going to Need a Bigger Boat

But there was a catch: I needed a bigger boat.

I needed a boat with two full sleeping cabins. My guests would get the good one and I’d take the lesser one, but the lesser one had to be a lot bigger than the lesser one on my current boat. I needed to upsize and I had a few models in mind.

Of course, all of these bigger boat options, although pre-owned, would cost a significant amount of money. I figured I’d get that money by selling my home, which is fully paid for, and my current boat, which has a small loan. (I could go into a long lecture about having a paid-for home, but I won’t do it here.) I figured I’d put all of the boat proceeds and half the home proceeds into a bigger boat and use the rest of my home proceeds to buy a modest place in Tucson. After all, although I love my current home, I don’t like it nearly as much during the four months I’d be taking my annual break from the boat. Surely I wouldn’t miss it.

When I was in Arizona, I looked at homes and land and actually found two different lots that were perfect for me. One would be easier than the other to build on, but I’d still have to build on it. I built my current home, acting as General Contractor while the experts did the stuff requiring experts and I did the rest. Did I have another build in me? I thought maybe I did.

American Tug
What a deal! This 2014 American Tug could be mine for just $610K! Not what I was hoping to spend, however.

So all this is what was going through my mind when I cut this winter’s trip to Arizona short so I could attend the Seattle Boat Show. I had multiple goals for the show, but the main one was to look at used boats in the marina portion of the show. And I did. I actually found two models that would work perfectly for my new business.

The unfortunate thing was that they cost about 50% more than I was hoping to pay. Oops.

Okay, well maybe I could get a small business loan. I had good credit and could work up a business plan that would pass muster. My number-smart brain — did I mention I have an accounting degree? — went to work considering possibilities to make this happen.

How the Current Political Climate Stopped Me Cold

Meanwhile, the demented old narcissist that half the country thought should be the most powerful man in the world got sworn into office. (Did you notice how he didn’t touch the bible? I think he was afraid he’d burn his hand with the lightning God would send through it.)

And things got pretty weird pretty quick.

I won’t go into a litany of the weird shit the Orange Clown and his South African crony, the Space Karen, have subjected America and the world to. First of all, I couldn’t list it all. I stopped following the news. All I know are the things that have crept through my social media filters, things I’ve heard while I had my head in the sand and my fingers in my ears singing la, la, la, la, la at the top of my lungs.

And even that is enough.

More than enough.

Boat Longing
There will be no return to Valcour Island in a boat anytime soon. But I will get to cruise the Pacific Northwest this summer so I’m not as sad as this picture might make me look.

More than enough to tell me that I’d be insane to invest time and money in a new business in this crazy political climate. Tariffs will result in inflation far beyond what we saw over the past few years. Job losses from the shutdown of government offices and the cancelling of grants will put people in dire straits. Another recession, which is definitely possible when the guy making laws by signing executive orders keeps making asinine decisions, will make it highly unlikely that anyone will want to pay me to take them on a cruise. (Unless there’s a chance I can smuggle them into Canada, I guess. If Canada even lets us in.)

More than enough to tell me that I’d be a complete and utter fool to walk away from a paid-for house to build a new one in the kind of economic uncertainty we face, where the price of lumber and building materials could jump 50% — if such materials were available at all. And in a red state? A place where the majority of people think calling the Gulf of Mexico the Gulf of America is a good thing that proves their cult leader has their best interests at heart? (How are those egg prices doing, my deplorable friends?) And how long before they cut our social security and medicare benefits — the exact thing most Americans in my age group are relying on to take care of them in their old age?

Am I nuts?

No.

So there won’t be a new business in my future. (Well, at least not one beyond the tiny business I started late last year and will talk about elsewhere.) There won’t be cruising in the freshwater lakes, rivers, and canals of New York and Ontario and beyond, at least not in a new-to-me, bigger boat. There won’t be a new house on five acres of desert land in the foothills of the Rincon Mountains near Tucson.

There will just be the financial security and comfort of the home I’m in now, a home I love eight months out of the year. I’ll keep myself busy enough.

And learn to be satisfied without chasing down another goal.

I still have that camper for a winter escape.

Facing Retirement

“Retirement,” which seemed so far off just last year, is now close at hand and remarkably easier than I thought it would be.


John’s Carver at its slip in Charleston, SC, on the night I boarded for our five week trip together.

Back in Spring 2022 — just 14 months ago? — I was on a cruise with Capt John on his 36′ Carver Aft Cabin cruiser on a trip up the Intracoastal Waterway (ICW). (You can read more about that in my Great Loop blog.) It was April and I was trying to enjoy the cruise while worrying about a bunch of work-related things back home:

  • Cherry season was coming up and I had all the usual concerns about the season. Would the cherry crop be viable? Would all my clients sign up? Would I get back clients who hadn’t signed up last year because of the frost? How much acreage would I have to cover? Would I need pilots in Wenatchee, Quincy, and Mattawa or just Wenatchee and Quincy? Would I be able to find enough pilots?
  • My helicopter N7534D, was aging and had just 20 hours left until a required overhaul that would cost $270K. I had already decided to sell it after cherry season, but was 20 hours enough for the season? What would I do if I flew that off?
  • Would I be able to sell my Part 135 charter business (which had become a pain in the ass because of the ineptitude and spite of inspectors at the Spokane FSDO) with a nearly timed-out helicopter? Would the guy who kept claiming he wanted to buy it all actually come up with the money?
  • Would I be able to find another helicopter to replace it without going back into deep debt? Or should I just retire from cherry drying? Would I be able to sell my cherry drying business to someone else who wanted to take my place?

All this was going through my mind as we cruised at 6 knots up the ICW, spending a few days at stops along the way. To be fair, my cherry season stress normally starts in March and April, but this year it seemed more stressful than usual, mostly because of the age of the helicopter and its upcoming need for an overhaul.

My idea of “retirement”

Wonder why I keep putting “retire” and “retirement” in quotes? It’s because my idea of retirement isn’t the same as most people’s.

I’ll never stop working. Whether I write or make jewelry or do odd jobs in the gig economy, I’ll always have something to keep me busy that brings in a few bucks. (Hell, this summer I’m even selling eggs from my chickens at $5 a dozen.) I’d already considered getting my boat captain’s license — yes, for a boat I didn’t even own yet — and doing charter cruises to earn cruising money.

I won’t stop working until either my mind or body makes it impossible. Working keeps us alive; you can ask my wasband about his dad’s short retirement to get an idea of what I mean by that. (I hope you’re resting in peace, Charlie.)

In general, although I had thoughts about retirement, it was still far off on the horizon. I couldn’t imagine being “retired.”

I did, however, have a rough plan for buying my own boat and cruising the Great Loop in it. I’d even looked at boats. But I couldn’t buy a boat unless I sold the helicopter and I still couldn’t buy a boat if I wanted to get another helicopter and stay in the business. So I figured the boat purchase would be sometime in 2024, after that cherry season. Maybe that’s when I’d “retire,” too.

Everything Changes

Everything changed with a phone call. A guy with a lot of money offered me a lot of money for the helicopter if I sold it then. He wasn’t interested in the charter business, but the amount he offered for a helicopter that I was hoping to unload in a few months anyway was too much to ignore. On May 6, I watched it fly away for the last time with the money secured in my bank account.


It was a lot easier to say goodbye to this helicopter when the money was in the bank and my thoughts were on the kind of boat I’d buy to replace it. Also, no more $20K per year insurance bills. Yippee!

I arranged to lease a helicopter for the season. (There were problems with that, but I won’t go into it here.) I got contracts, I got pilots. The season started off good and then fizzled out in mid June when it stopped raining. The season ended in August. I heaved a sigh of relief again.

I listed my charter business with a broker. I knew that I’d have to get a helicopter to keep my Part 135 certificate and I’d decided that I was done owning helicopters. The broker listed it for a lot more than I expected.

Meanwhile, with all that helicopter sales money sitting in the bank, I started shopping for a boat. By the end of August, I’d made a deal on one.

Around that time, the broker found a few buyers for my company. One backed out. The other was an idiot tire-kicker who called me directly with a crazy lowball offer. But the third was serious. As I was signing papers on DocuSign to buy the boat, I was signing other papers on DocuSign to sell my company.

And suddenly, I found myself with a nearly new Ranger Tug, a new company that offered just cherry drying and aerial photo services, and a bunch more money in the bank than I expected to have at the end of cherry season. I’d also shed a costly-to-keep helicopter, a charter business I no longer wanted, and the anxiety of dealing with unreasonable, demanding people at the FAA.

I celebrated by spending September learning to cruise in my new boat. Then I shipped it to Chicago and got it on the Great Loop.


While I’m home this summer, I can be reminded of my first day on the Loop with the new Home Screen on my phone.

I named my boat Do It Now. Frankly, I was done waiting. Hell, I’d been done way back in 2010 but had a husband to shed to move forward. It had taken me 12 years to get through the divorce debacle and become financially secure in my home — which I’d paid off in July 2022 — before I could get back on track for what I wanted out of life.

But I didn’t think that I was one big step closer to “retirement.”

Retirement Thoughts Kick In

It wasn’t until this past winter that I started thinking about the possibility of tapping into the retirement money I’d been saving in earnest since the late 1980s. I own some stock — including Apple stock I originally bought at $13/share in the mid to late 1990s that had grown substantially with numerous splits and stock price increases. And I had some savings. And my living expenses were pretty low since just about everything I owned was completely paid for.

I’d been under the impression that I had to wait until I was 65 to start tapping into my retirement funds. Or maybe it was 62? I asked a knowledgeable friend. No, he told me. 59 1/2 is the age you can start using that money.

Holy cow. I was there.

I had a great winter cruising on the Great Loop in Do It Now, covering 3000+ miles, mostly solo. I made friends, saw a lot of new places, and met challenges along the way. I took a seven-day captain’s license class and passed the test.

But as March and April came along, I had the same cherry season worries as usual, but with a twist: I didn’t have a helicopter to fly. How was I going to deal with that?

Various solutions came about and I explored them all. But it wasn’t until I started contracting with clients that I realized what a non-issue it would all be. One of my clients did not sign up again. Since he accounted for about 2/3 of the acreage I cover, my season would be a lot shorter with fewer pilots and less revenue to pay them. I’d be able to keep a lot less money.

At first, I was angry. But then I reasoned it out. I wanted to to retire at the end of the season anyway. I was hoping to be able to sell the business, but if I had a good enough season, I might talk myself into keeping it and doing it again. But this one client had helped me make two decisions that took a lot of stress out of my life:

  • Without the added acreage, the business wasn’t worth selling so I didn’t have to stress over finding a buyer (or dealing with the tire-kicker who claimed 3 years ago that he wanted to buy my whole business).
  • With less revenue coming in, it was less attractive to keep doing the work. I was no longer tempted to do it another year. Retirement at the end of the season was a definite.

And I’ll be honest here: the client who had backed out was a pain in the ass anyway. Now I wouldn’t have to deal with his antics.

No, I haven’t been drying cherries for 25 years. It was only 15 years. Before (and during) that time, my summers were ruined by book deadlines, mostly for Quicken Official Guide, which I wrote the first 11 editions of starting in 1998.)

I was looking at the reality of having a summer off in 2024 for the first time in 25 years. It took no time at all to imagine my trip up to New York that summer for the ultimate Champlain, Erie, and Severn Canal cruise in my boat.

And with that, I had scheduled my retirement: August 2023. I would be 62 years old.

The Money Stuff

The question was, could I afford retirement without changing my lifestyle? I have to admit that cruising in a boat thousands of miles over the course of months is not exactly cheap. If I wasn’t going to make enough cherry drying money this summer to cover the next year of cruising, where would the money come from?

The answer was easy: my retirement funds.

They’d been growing and shrinking and growing and shrinking but mostly growing over the past 30 years. If I continued to earn some income from other sources, I wouldn’t need much every year — probably not even enough to start getting social security anytime soon. After all, other than cruising my cost of living was modest. (It really pays, folks, to eliminate all your debt before you retire.)

I had a talk with my accountant yesterday and a “retirement specialist” at my investment firm today. I discovered that my lowered income would save a lot of money on taxes, get me a better ACA health care subsidy until Medicare kicked in in 2026, and enable me to make retirement plan withdrawals without huge tax hits. I also discovered that tapping into my IRA would be as easy as filling in a form on my investment website. The money would arrive within days as a direct deposit to my bank account.

Of course, the money I’ve invested in my retirement funds is not unlimited. I will eventually run out. How quickly that happens depends on the stock market and how much I take each year. But I still have Social Security waiting for me and can always sell my home on the next market upturn. I think I’ll have enough for the rest of my life.

That is the goal, isn’t it? To die with just enough money to dispose of your body and give your friends a big party to say goodbye?

Facing retirement? Yes, but also embracing retirement. I just didn’t expect it to be this soon.

One Way to Do Twitter Wrong

Some people don’t get it.

Last night, before going to bed, I took a moment to check Twitter notifications. I found two tweets from someone I didn’t know who had mentioned me without actually tweeting to me.

I’m not going to embed them here because I don’t see any reason to give this idiot any additional attention. But he’s a perfect example of someone trying to use Twitter to move markets — when he only has 49 followers.

Here’s the first one:

Idiot Tweet

He was referring to a blog post I wrote years ago about Groupon. I think he’s trying to say, in his semi-literate way, that if I advertised on Groupon, I could fill otherwise empty seats on my aircraft with Groupon customers. Apparently, he thinks these people will appear just when I need them and be willing to sit around and wait until I do.

Of course, his theory doesn’t apply to my business because I only fly by appointment and I don’t have seats that are not paid for. So why would I be willing to discount flights by 75% — which is basically what Groupon requires* — thus taking a deep loss on every Groupon deal flight? That was the point of my blog post.

He then replied to that post to add this:

Idiot tweet 2

Not very bright? Well, at least I can string a sentence together, buddy.

My response was simple: “Fuck off.” I then responded to the first tweet by thanking him for the link and following it up with a simple “LOL.”

And that’s when I discovered just how dim this guy is.

He responded:

Idiot Tweet 4

Not personal? He said I wasn’t very bright. That isn’t personal? And does he honestly think being a Twitter user with 49 followers gives him any clout? Enough clout to get me to delete a 6-year old blog post with dozens of comments?

I responded “Is there something about “fuck off” that you don’t understand?” (Yes, I know. I can be a real bitch. But if you had any idea of the kind of trolling I’ve dealt with over the past few months on Twitter, you’d understand why I now have zero patience for idiots on Twitter.)

But it was his response to my tweet thanking him for the link that proved how really dim he is:

Idiot Tweet 3

He didn’t realize that by including a link to my blog post, he was actually sharing it in his Twitter stream. Giving it more exposure. Best of all, he’d done it with a #GRPN tag, increasing the exposure beyond his 49 followers. Anyone looking for the #GRPN tag — people actually interested in Groupon — could potentially see it.

And bash him? Why would I want to do that? If I wanted to bash him, I could do it here by simply embedding his tweets without redacting his identity. But I’m not. Instead, I’m ridiculing him while keeping his identity anonymous. Truth is, I feel sorry for him. He’s so amazingly clueless.

So, to sum up, this clown unwittingly shares my blog post about Groupon with a #GRPN stock tag, says I’m not very bright, and then offers to delete his tweet if I delete the post.

I went to his profile to take a look. It was full of Groupon company and stock related tweets. They guy is an investor — that’s clear. For some reason, he thinks he can use Twitter to influence the price of Groupon stock or get more people to sign on for their “deals.” He’s big on tags like #ecommerce, #investing, #socialmediamarketing, #stocktips, and, of course, #groupon. He could be a bot, but even bots aren’t that dumb.

So I blocked him. He’s still probably trying to figure that out.


* Do the math: Groupon wants a 50% discount “deal” and then keeps 50% of the discounted price. That leaves me with a total of 25% of the original price.