Flipping Out!


How I Learned to Appreciate My Mistakes and Bring Focus to My Watch Collection

Excessive watch flipping is frowned upon amongst watch enthusiasts. If purely for profit, it can create rather expensive bubbles in the market. Just try to buy a new Rolex sports model in steel at your local AD, or better yet, try to buy one used from a grey market dealer. Neither are enjoyable experiences, and excessive flipping for profit has definitely contributed to this reality.

Frequent flipping can also be seen as a financial liability for newcomers to watch collecting. Such a circumstance  can leave a sour taste in a collector’s mouth for years to come. Watch collecting is one of those activities in which experience and information can be demanding teachers.

For me, 2020 was a total “flip out.” I took a relatively expensive trip down horology lane in search of one watch dress watch to add to my modest collection, consisting of one vintage two-tone Datejust and a modern six-digit Submariner. Somehow, I ended up buying eight watches and selling seven in just under nine months.

One way to look at my experience in 2020 is that I really only added one watch to my collection, going from two to three, and lost some money in the process by making quite a few rookie mistakes. However, I prefer to look at the entire experience as one in which I was able to learn three important lessons:

  • which types of watches I don’t particularly prize;
  • which can sometimes be as satisfying as finding out which ones you do have an interest in pursuing;
  • how to trust my instincts and buy what I like.

More importantly, at least in my case, I learned that I am much happier when I narrow the focus of my enthusiasm for watches. At least until I am satisfied that I am ready to move on from a genre. Being a watch enthusiast can be overwhelming nowadays given how much watch-related media there is on the internet.

A Year to Remember

2020 started on a very optimistic note for me. I was starting a new job, I ran a marathon on January 17th and posted my PR, on February 5th, I made it to 1 year of continuous sobriety, and my wife and I were going to celebrate our 10th wedding anniversary in October. For a watch enthusiast, any one of these events would justify adding a new piece to the collection. I was no exception. I planned to purchase a watch sometime in 2020 to commemorate all the above occasions.

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When it came time to figure out which watch I had wanted to purchase, I didn’t have a game plan. I have been a watch enthusiast as for as long as I can remember, and I have a deep appreciation for many types of watches and brands. I was still enjoying the two watches that I already had in my collection, but I had two months in-between leaving my last job, and starting the new one. During this time, I discovered all of the new watches, and watch-related media content that the community had produced during my hibernation from collecting. So much information was available, and in so many different formats.

In 2014 I bought my first real time piece to commemorate completing my MBA and getting a promotion at work. For many years I had wanted a Rolex Submariner, and I finally bought one. In the same year, I had been gifted my father’s 16233 Datejust. It was the watch that my stepmother had bought for him in 1989 when he had graduated with his MBA. I now had a solid two-watch collection. One heirloom vintage Datejust, and one current model 114060 Submariner that I bought with my own hard earned and saved cash. This held me over for  five and-a-half years, but I always did have reservations about the maxi-case on that 114060.

At the beginning of 2020 my enthusiasm and capacity for learning about watches was very high. Plus, I was blown away by all of the information that was available on the internet, in print and on podcasts. I was ready to go down the rabbit hole.

I really quickly dove deep into the new episodes of Talking Watches that Hodinkee had produced since I had been away from the scene. I also found Watchbox, and more specifically Tim Mosso’s Encyclopedic knowledge of just about every brand, model and movement in the world. It didn’t stop there. I devoured all that I could. To this day, I am still finding new podcasts, blogs, websites, micro-brands etc. I truly cannot believe how fortunate we are today to be able to learn so much information, in such a short amount of time, from such talented and passionate people. All that information can overwhelm a newly serious watch collector.

So how do you go about choosing what kind of watch to buy when you have only set a budget, and haven’t any idea of which brand, style, or time period you would like you for your next purchase?  Since I had been spending all of my free-time consuming watch-related content, even listening to watch-related podcasts on my morning runs, I was going in a million directions with my thought process. Simultaneously learning about something new and lusting after said thing, day in, and day out.

On occasion I would be very clear about my intended next purchase. Sometimes the watch I had in mind stayed there for days, but then I could change my mind in a quick tick. One day a simple, elegant three-handed, time only, vintage dress watch was what I thought that I must have. The next day a modern 44 mm dive-chronograph – still a genre that I am extremely attracted to, but don’t know why-that was DLC coated, with a ceramic bezel.

Like anything in life, if you are a watch enthusiast, you have to make mistakes in order to learn. You need to get out there and into the game. Note in the table below that only two of the eight watches I purchased in 2020 are still in my collection. Those were keepers.

Watch Shopping in Europe

In the last week of February, I embarked on a two-week work-related trip, armed with two months of daily watch content intake. I planned to spend one week in Germany visiting several clients and to spend the following week at one of my company’s manufacturing facilities. I would stop in Paris for a weekend in between.

I had a day and a half to spend walking around and taking in Paris, with only a very vague idea of the watch boutiques I had wanted to visit, and watches that I wanted to try on. This proved to be too much for me to handle without a plan.

The first place I hit up was Breguet -which was absolutely breathtaking as they have a museum there on site – and tried on several Classique dress watches, and Type XX chronographs. All beautiful watches, but I knew I needed to do more homework before making a purchase I might later regret.

Then off to Patek to try on a 5196 Calatrava and to try and fake that I had the funds to even consider purchasing a 5130G World Timer. I sensed that they knew that I didn’t have the means or guts to buy any of the grand complications. I moved on.

Next stop, Vacheron Constantin. This brand has always captivated me. Especially their mid-century ultra-thin dress watches. They’ve been in continuously production since 1755 and are kind of the dark horse of the “Holy Trinity.” There’s just something amazing about that Maltese Cross logo that grabs me. The Overseas, Historiques Triple Calendar 1942 and American 1921 and Patrimony that I tried on were all fantastic watches. I wanted every one of them, but knew that in wanting all of them equally badly, I shouldn’t buy any of them. I was impressed with my restraint during my first three visits.

After Leaving Vacheron, I headed over to Jaeger-LeCoultre. I was convinced that I wanted the Ultra-Thin Perpetual Calendar in steel with a silver dial. This would really have stretched my budget, but to me it was such a cool, and under-the-radar piece for so many reasons. I also thought that it would catapult me into the realm of being a “real collector”. After several minutes of discussion with one of their salesmen, he had let me know that they had one left, and that although someone had potentially expressed interest in buying in, they would call that person to follow up, and if they were no longer interested, they would sell it to me. My heart raced. I told them I’d return the next day, and allow them to make their call to the other client.

When I came back the next day, I was informed that the client was about to come in and pick up the perpetual calendar. In a way, I was relieved. I knew deep down that I would have been leaping into a watch that I was trying to like. I was in uncomfortable territory in both monetary and horological terms. It is a fine timepiece, but it doesn’t quite suit my current lifestyle, which includes running, biking, and chasing after two daughters, who are 5 and 7 years old. This is not to say that I don’t like or someday want to own a fine dress watch; but it just wasn’t the right time, or right piece. I shouldn’t have to talk myself into a watch like this, or constantly ask others their opinions of it. When it’s time for a watch like this I will know it.

I continued to  explore some of the watches I had obsessed about on the Jaeger-LeCoultre website, and at my local Metro Detroit authorized dealer. After trying on about five different watches, a panic came over me that I might end up leaving Paris without a watch and wouldn’t know when I would be able to come back. This was irrational thinking, as I didn’t know what I really wanted to buy yet. Besides, Paris isn’t the only place in the world I could buy a watch once I had decided which timepiece I really wanted.

Nonetheless, I impulsively purchased a Reverso, knowing deep down such a purchase was premature. As a watch enthusiast, I have always appreciated Reversos, and loved the story of their origin in 1931. They are truly iconic, and one day I would really like to have one; but it will be the right time and the right model.

In this case, I had let the salesman talk me into purchasing the largest sized reference, which has a small seconds hand register that I felt was not aesthetically pleasing. I had always thought that the Reverso looked better as a simple two-hander in the medium size, but I was caught up in the atmosphere of the boutique, which included the flattering words of the salesman, and ended up going against my instincts. I had made this mistake many times when purchasing luxury goods in the past.

I now was the somewhat happy owner of an elegant, rather dressy and iconic timepiece,

despite it originally being a sport watch. I felt like I should have been content. Afterall, the Reverso is “a choice that someone who is refined and confident would make.”  “It’s timeless, and “Everyone’s collection should have one.” I had picked up  such opinions while reading, watching, or listening to watch-related content in the weeks leading up to my trip.

I was satisfied with my Reverso for about a week after returning home. My wife and mother both applauded the purchase. My mother even said that she was jealous and wanted one herself. Still, it didn’t take long until I was lusting after another watch. Another watch that I thought I needed to have to be a serious watch guy.

Everyone Needs a Speedmaster in Their Collection

Omega Speedmasters are awesome. I mean, for the money, can you name a better watch experience for a watch nerd than a hand-wound, steel chronograph with an extremely legible black dial, that has a resume that includes being worn on the moon?!  I figured that since I had only bought a base model steel Reverso thus far in 2020, and thereby only spending less than half of my budget, that it made sense to buy a Speedy as well. After all, “Everyone’s collection needs a Speedmaster.”

I opted for the First Omega in Space  (FOIS) variant as I was sold on the straight lugs, and slightly smaller case size.  I used to be absolutely convinced that my wrist was extremely small and that I shouldn’t wear watches that were larger than 40mm in diameter and that watch companies were foolish to continue to make larger sized watches (I was still processing  the viewpoint du jour). I decided to go with Hodinkee for the purchase rather than the grey market. I trust those dudes over at Hodinkee and wasn’t quite comfortable with buying from someone I didn’t know by using podcasts or YouTube. I asked for them to throw in an extra strap to help me rationalize the price difference between them and a grey market vendor, and within a week, I was the somewhat proud owner of Speedmaster, a Reverso, a Datejust and a Submariner.

Lessons of Joy and Regret

It didn’t take long for anxiety to set in for several reasons. First of all, I now had four watches, and unless I wanted to be “that two-watch-at-a-time guy”, only one wrist to wear them. I was starting to feel like I had to wear them all, rather than wanted to wear them all. Right out of the gate, the Reverso became the watch that I felt sorry for. The one that I bought on impulse and didn’t carefully pick to be on my team. That made me feel sad. I had just bought it, it was a fantastic watch that should bring joy to many other people, and wearing it had already become a chore. How did this happen?

The second lesson I learned was that I had simply purchased two base-model luxury watches, neither of which I had spent months researching, let alone years admiring, thereby spending most of my watch budget for 2020. I knew deep down that I had been impulsive, and went for instant gratification. Not once, but twice. But I wasn’t done yet.

Within two weeks of adding the Speedmaster to my collection, I had been bitten by the Daytona bug. A watch that I hadn’t really given much thought to in the past had now become something that I thought that I must own. A lot of the  content I was consuming opined over Paul Newman Daytonas. I knew that I would never have the money for one of those, but I did fall hard for the notion that if I were a smart collector, I would snatch up a Daytona with a Zenith El Primero movement, and keep it forever, or at least until it sky-rocketed in price. Afterall, they were “bargains”, and the “El Primero movement is a watchmaking icon.”

There were two problems with this spell the Daytona had cast on me:

  • I had never worn a Daytona to see if I even liked it.
  • I was now entertaining this buy with the mindset of a watch market speculator, which was not my vocation or intention at all. This was supposed to be something that I did as a hobby, not something I was going to bet my financial future on!

Despite being conscious of these two problems, I trudged on and sold-off the Speedmaster and Reverso that I had owned for less than two months to make room for a 1999 16520 (steel with white dial) Daytona. I had rationalized the purchase, and loss I incurred on the sale of the other two watches, by saying to myself that this is “the one.”. I would keep this watch forever, and it would give me mad-street cred with the rest of the community. I was already talking “exit” watch. It was like I was treating my enthusiasm for watches like a job that just needed to get done and put behind me.

As soon as I opened up the package from Watchbox that had my 16520 inside, I felt a sense of dread. It didn’t make me smile. Right away I was thinking that it was someone else’s watch from 20 years ago to perhaps mark an occasion in their life. That would have been great if that someone was my father, or someone else I knew, but it wasn’t. I didn’t know where that watch had been. I didn’t know the story of that watch. For some people that is okay, and perhaps one day it will be for me too, but at that moment, I wanted to either buy new and make my own stories in the watch, or at least understand its provenance.

The other issue I had was that as soon as I put it on my wrist it felt lifeless to me. On my computer screen, zoomed in by a factor of 2-8x, the watch looked fantastic. Bright and legible. Timeless. What I was looking at on my wrist didn’t have the same presence, or at least, it wasn’t what I had expected. It wore smaller than I had anticipated, and it was very hard to read. To make matters worse, I took it with us on a family trip down to Charleston later that week, and I was afraid to wear it. I felt like it was on loan, and I didn’t want to be the one to add any patina to it.

During our trip to Charleston, my wife and I stopped into a jewelry store that was a Grand Seiko AD. I had seen the SBGW 231 online before, but I wasn’t ready for how amazing that dial was in person. All of the Zaratsu polishing that everyone talks about is the real deal. The hour indexes looked like diamond baguettes. The SBGW 231 is a roughly 37 mm time-only dress watch, with a beautiful cream-colored dial, and I had to have it. The rest of the trip, and the whole way home, while driving, I could barely take my eyes off of the thing. There were two little problems with it, however:  I felt like it was too tall for its diameter and didn’t seem to look right on my wrist as a result. The other issue I had with it was the crown. It simply looked too big to me. Those two little problems never went away for me.

I was now back to having four watches, and the two newest editions to my collection, the Daytona and Grand Seiko, were my least favorite. About two months later, I made a call to the dealer I bought the Daytona from, and sold both of my latest purchases to them.

As soon as I left FedEx after shipping my Daytona and Grand Seiko off to be sold, I felt a sense of relief, and a sense of excitement that I was going to be able to go back out into the market to purchase something new. Instead of savoring that optimism and realizing that being impulsive had put me in a position of having bought and sold four watches in six months, and as a result, had lost a bit of money, I went right back at it. Within a week I absolutely had to have a Vacheron Patrimony.

When the Patrimony arrived, I was somewhat ecstatic. I say somewhat because despite being blown away by the unboxing experience, and just generally being excited to own a timepiece from one of the “holy trinity”,  doubts began to bubble up. I was suddenly questioning my choice of yellow gold versus white gold, regretting that the strap was brown rather than black, and within about two days, wondering if I had purchased the wrong model. I had started to think that I would have been better served to buy a steel Historiques 1942 Triple Calendar. Any one of those three thoughts would have spelled trouble. They surely signaled to me that I had once again moved too quickly and had bought what I thought I needed in my collection to be a real enthusiast.

It was during the month that I waited for the Vacheron to arrive that I learned about Sinn watches. They are rugged, no-nonsense German made tool watches that are extremely well priced for what they deliver. Afterall, the Sinn EZM 1.1 was the exit watch of Tim “The Man” Mosso, who had sold off his amazing JLC collection, and now only wore that watch. My favorite were the pilot watches and diving chronographs. I had become obsessed with finding one watch that did it all. After a week or two of scouring their website, and the internet, I had decided on the 900 S. A black DLC-like coated 44 mm Pilot chronograph with a heavily modified Valjoux 7753 movement. This thing also had a GMT function and was water resistant to 200m. The list of technical features that this thing had was a mile long. I had started to think that this may be the absolute perfect watch for me. The only thing that intrigues me more than a dive-chronograph is a pilot-dive-chronograph.

Within a period of a little over one week, I had received my Sinn and Vacheron in the mail. First came the Sinn, and I immediately knew, that while it was an impressive piece, it was not for me. The reasons why are too numerous to list, but I knew that someone else would enjoy the watch far more than me. I was now staring down the barrel of having two more watches that I was willing to sell.

One morning I read an article that was written by Aurel Bacs, the Head of Watches at Phillip’s, the famous auction house. His article was about his love affair with Datejusts, more specifically, the 36 mm, stainless steel 16200, with a white dial, a smooth bezel and a jubilee bracelet. It was the watch that Paul Newman wore in “The Color of Money.” In the article he also went on to compare it to the reference 126300 that Rolex released in 2017. It is 41mm in diameter in stainless steel, has a smooth bezel, a jubilee bracelet, and a simply breathtaking blue sunburst dial. I was mesmerized by the new 41mm Datejust pictured in the article. I also loved the story about Aurel having the same version that Paul Newman wore in the movie , and that he went on to purchase the 126300 and loves it, despite him owning and having access to many pricier steel sports watches given his position within the watch industry. I also liked the idea of adding the new reference to my collection to sit alongside my favorite watch, which is the Datejust that my father gave me.

I texted someone at my local Rolex AD immediately after reading the article, asking if she could get me the 126300 that Aurel had written about. Miraculously, she told me that she had just found out that the shipment that was coming in later that afternoon had one in it, and that if I wanted it, I could have it. I went to pick it up later that afternoon, and it has been on or near me almost every day since. I unloaded the Vacheron and Sinn within the next several days to make room for this beauty.

I was now down to a much more manageable, and congruous little collection that represented my personal style and interests at this point in my watch journey. When looking at my Submariner and two Datejusts, I found myself smiling. I found myself wanting to wear each of them. I still had one little problem, however:  the lugs on my 114060. I hadn’t liked the maxi-case from day one, and always had wished I would have purchased the Seadweller 4000 (ref. 116600) that was there that day instead. Unbeknownst to me, several years earlier Rolex had released a new Seadweller, and it scratched every itch that I had.

The 2017 Seadweller (SD43) is amazing in my opinion. Despite being a significantly larger watch than my 114060 – 3 mm larger in diameter, and 3mm taller – the lugs are slimmer, and in combination with a 22mm lug with, the watch carried its extra size much more elegantly. The new SD 43 also had two other features that I loved. It had the cyclops, which I had finally admitted that I liked because it is extremely functional, and it says Sea Dweller in red text on the dial, which is a nod to the original single-red Seadweller from 1967.

I had tried on a two-tone version at my local AD back in October of 2020, and I was amazed at how wonderful it looked and felt on my wrist. At the time I hadn’t thought to ask if they could get me a steel version, as it’s almost taken as a joke nowadays given the extremely low supply, and extremely high demand of all steel Rolex sport watches. I decided to sell my 114060 Sub after trying on the two-tone. I knew that even if it was going to be years for me to get a steel version, I wanted to have an SD43. It was closer to what my heart wanted back in 2014. This time I was going to go ahead and wait for what I really wanted.

Finally, in early December, I asked my AD if I could place an order for the Seadweller. I had made a nice profit on my 114060, which was a pleasant surprise. They allowed me to place my order, but I was quoted a lead-time of 2-6 months, and possibly longer, due to high demand, and COVID 19. Miraculously, within 10 days after placing the order, I received my watch!  I couldn’t believe it when I got the call from the AD. I thought they were going to tell me that they had to cancel the order and refund me my deposit. Instead, Christmas came a bit early.

I walked into the AD with a smile from ear-to-ear. I’m lucky I didn’t get into a car accident on the way there because I was essentially floating in space due to the adrenaline rush I had from the call. My smile only widened when they opened up the clear plastic box that the watch was in to put in on my wrist before being adjusted, while they fetched the famous green box that I would take home with me. I couldn’t stop staring at the watch. I still can’t stop staring at it.

So, after all that I put myself through in 2020, I really only added one watch to my collection. Okay, I made one upgrade from Sub to Seadweller, and added a Datejust, but to anyone who is not a watch enthusiast, it would simply look like I added one watch. But to those of us that enjoy this hobby, I had a tumultuous run for being somewhat of a beginner. What’s ironic, is that after all of the self-inflicted gyrations I went through, I naturally made my way back to what makes me happy. What I have realized is that in a sea of endless possibility, the only way I can successfully navigate is to trust my instincts, and to narrow my focus.

When I look at my three watches together, I’m humbled to have the chance to possess such beautiful objects, one of which was handed down to me, and all of which I hope to hand down to my children, and / or their children. I like the way they fit together into the small niche that I am naturally drawn to. Anyone of them could be a “one-watch-collection.” I still have a lot to learn about the history of the Datejust and Seadweller, let alone Rolex in general. There’s a Rolex Deepsea ad that I came across on Ad Patina a few weeks ago that sums up the way I feel about learning about anything in life. It has James Cameron on it, and he is coming out of the submersible craft that he piloted down into the Mariana Trench, some 7 miles deep. The caption says:  THE DEEPER WE DIVE, THE MORE WE DISCOVER. love this simple message and think that it applies to many things in life. Including watch collecting.

I feel good about where my Datejust collection stands: one old, one new. One piece is actually borrowed because I plan to have it engraved and to hand it down to one of my daughters someday. The other one is blue. But the Seadweller has made me want to go deep into dive watches. Maybe Rolex for now. There’s a lot of meat on that bone. Maybe I will move on to other brands like Glashutte, Panerai and Omega that have always intrigued me. Maybe I’ll even get a dive-chronograph, which could be my vector into not only a new brand, but also the chronograph genre in general. Either way, I’m going to let my instincts guide the way.

Editor Note:

You can also watch a video of the Sea Dweller that Jake now owns here.