Category: Retirement

Onwards

We sold our house and left San Jose, CA on October 22, 2022 to pursue my nearly lifelong dream of cruising on a sailboat in the Caribbean. I get bored with the same-old and we’ve been living in California for nearly 18 years but now it was time for something new. Something to push us out of our comfort zone. Something that was going to introduce us to new people and places.

For months prior to October, we spent our time packing and planning. Packing a house of 3500 sq. feet and things we and our three kids have acquired over 18 years was much more challenging than I had imagined. We finally packed up the U-haul on October 22, 2022 of the items we staged to go to the boat and some things that didn’t fit in the Pod that we were sending to Sarasota, FL, our new residence. At the time of writing this, we have 4 storage rooms. Three in Virginia and one in Florida. Two of the storage units in Virginia will ultimately be emptied when we finally return to Virginia to put While One on the hard in June. JK Moving has the rest of our household belongings for long term storage.

I thought I’d start this blog to capture all of the places we’ve either visited or passed through since starting this adventure. This will be a living blog, updated as we visit new places.

San Jose, CA to Sarasota, FL 2022 — 4000+ miles

  • Gilroy, CA
  • Los Banos, CA
  • Kettleman City, CA
  • San Fernando, CA
  • Glendale, CA
  • Pasadena, CA
  • San Bernardino, CA
  • Palm Springs, CA
  • Palm Desert, CA
  • Blythe, CA (The last place we got Gas at and paid California prices!!!)
  • Quartzsite, AZ
  • New Hope, AZ
  • Phoenix, AZ
  • Tucson, AZ
  • Benson, AZ
  • Wilcox, AZ
  • Bowie, AZ
  • San Simon, AZ
  • Lordsburg, TX
  • Deming, TX
  • Las Cruces, TX
  • White Sands, TX
  • Santa Rosa, TX
  • Tucumcari, TX
  • Amarillo, TX
  • Pampa, TX
  • Canadian, TX
  • Enid, OK
  • Tulsa, OK
  • Little Rock, AK
  • Memphis, TN
  • Nashville, TN
  • Hendersonville, TN
  • Cardiff, TN
  • Knoxville, TN
  • Asheville, NC
  • Statesville, NC
  • Cornelius, NC
  • Charlotte, NC
  • Kannapolis, NC
  • Greensboro, NC
  • Durham, NC
  • Raleigh, NC
  • Wake Forest, NC
  • Richmond, VA
  • West Point, VA
  • Mathews, VA
  • Williamsburg, VA
  • Yorktown, VA
  • Gloucester, VA
  • Beaufort, NC
  • Jacksonville, FL
  • Tampa, FL
  • Ocala, FL
  • Sarasota, FL

Sarasota, FL to Fort Lauderdale, FL (214 Miles)

  • Venice, FL
  • Cape Coral, FL
  • Naples, FL
  • Fort Lauderdale, FL

Bahamas 2023

  • Alice Town, Bimini
  • Bailey Town, Bimini
  • Great Harbour Cay, Berry Islands
  • Chub Cay, Berry Islands
  • Spanish Wells, Eleuthera

The Transition is Hard

It’s 75ºF at 5:30pm as I sit in my bean bag chair, eagerly awaiting yet another peaceful, beautiful sunset. I’m not sure what I expected at this point transitioning into a new lifestyle.

Despite folks repeatedly telling me how relaxed I look, I’m not sure I completely feel what they suggest they’re saying. It must be true…at least, I must be way more relaxed than I presented when I was working full-forced at Apple in Cupertino. However, I’d be lying if I told you I felt completely relaxed. Why? What’s going on? Where did I think I’d be in terms of my mental health sitting at Great Harbour Cay in the Bahamas at the end of January?

Clearly, I had a lot of expectations. Winding down my employment at Apple has been far harder than I ever anticipated it would be. I did expect some of the feelings that I’m having, but I guess I didn’t think they’d be so pronounced. It’s tough. After working nearly 18 years at Apple, I don’t know why I think I’d be able to unwind in a few months or less. I’ve spent my entire career at Apple and prior literally killing myself, giving everything I could to the company that fed my family.

It’s so very tough to be working right now. Despite my best efforts of setting expectations to my management and with myself, I find it so very hard to walk the line of earning my paycheck and putting in the 100% I’m accustomed to giving my employer and completely divorcing myself from all that I work on. I don’t know how to do it. I’ve not had to do it before. To be fair, I’m very gracious that Apple has provided this opportunity. I don’t want to leave on a bad note.

I suspect that once April comes, I’m going to go through yet another phase of this lifestyle change. No paycheck. Nothing to schedule may day around other than what I want to do. Until then, I find myself teetering between eagerly anticipating April yet trying to remember to live in the moment and appreciate now for what now is.

29 Day Check-in

We showed up at Zimmerman’s marina in Mathews, VA on November 4th. Today will be about the 29th day I’ve woken up on the boat and so I thought I’d capture some thoughts on this journey.

We’ve had several interruptions along the way. The first handful of days were spend on the hard trying to get the boat ready. Then, there was a couple weeks of waiting for the weather to leave Virginia and round Hatteras. A week or so waiting around in Beaufort, NC before finally throwing in the towel and renting a car to be able to take delivery of our POD at our Sarasota house. Then we had several weeks waiting for the weather in Sarasota before finally making the crossing to Bimini.

A little less than a week at Bimini and back to the states we flew to spend Christmas with family. Good grief, it’s been a tad bit crazy. An now we’re getting ready to close up the boat again for a week as I need to fly back to Cupertino for work.

Suffice it to say, Sherine and I are still trying to figure this whole thing out. We have to remind ourselves this break in ritual is exactly why we set out to do this. We get board with the monotony of the same-old schedule week after week. I’d be lying if I said juggling work with the necessity of traveling back and forth to the states or waiting for the weather wasn’t difficult or a tad frustrating.

I’m starting to recognize now that many of the frustrations, anxieties and challenges I feel now I’ve brought with me and that they haven’t been caused by this new lifestyle. I guess I always had the sense this was the case but had somehow convinced myself this new lifestyle would resolve everything.

Don’t get me wrong. This lifestyle has been doing wonders. While I sit here and complain about the stress, frustration and anxiety I still have, it’s not to say it hasn’t gotten progressively better. At least for me, it takes work and that for anybody considering this lifestyle, don’t be trapped into thinking it will solve all of your problems of your conventional life.

So, there are a few things I can note that we need to work on.

  • Sherine and I are still working and since Apple is 3 hours behind us, this is particularly challenging. We have not been very good at communicating and planning this time in the morning before which Cupertino finally wakes up.
  • The time difference also makes it difficult to plan for exercise and also meals. 8pm EST is 5pm PST and to wait until then to eat doesn’t sit well with my stomach. As a result, I’ve not been a particularly good partner in the making of meals. I’m not sure what the right answer here is other than to try to do better on my end to re-schedule my evening meetings — something which has proven to be difficult to do.
  • We’ve got to figure out how to get regular exercise into our life. On one hand, we are a tad bit more active than when we’re on land, I think. Boat life is not easier than on land, it’s harder…even if it’s just by 10%. That said, one of the reasons for getting out of the rat race has been to focus more on our health and this new lifestyle has been far from successful in allowing us to do this.

Goodbye San Jose, it’s been real

We’ve lived in San Jose since 2005. We moved here as young parents of a seven, five and three year old. It was terrifying moving to a town/state where we didn’t know anyone or had any idea where to live. Fast forward 17.5 years later, I look back at all the blessings San Jose has given me and my family.

Thank you San Jose for providing me opportunities I could never have imagined. I was blessed enough to be able to be a full time stay@home mom. Being a very active mom of three very active kids has given me times of being a soccer mom, football mom, basketball mom, swim team mom, cross country mom, wrestling mom, baseball mom*, waterpolo mom, band mom, volleyball mom… you name it, my kids did it and I was so lucky to be a part of all of it! I had the chance of being president of a little league and a home&school club, starting an anti-bully program in a middle school (that is still running!). My motto for volunteering was “How hard could it be?” And I loved every minute of it.

Thank you San Jose. After all the mom years, I was able to return to my career. Never would I have imagined being offered a Returnship opportunity at one of the coolest companies in the world, making the coolest product! The last 3.5 years working for Apple has given me so much joy. Being a stay@home mom, I put my personal goals and needs in the back seat. For the first time in a long time, I was able to pick up where I left off as a firmware engineer and accomplish a set of personal goals just for me!

Looking back at the last 17.5 years, things weren’t always perfect. At times things were flat out difficult, but God has been great to me and my family and blessed all our years in San Jose.

The Date is Set

I had a 1:1 with my boss this past June, like we often have weekly. Besides status updates on a variety of project, he would often ask me on how sourcing my replacement were coming…and it wasn’t going well. Recognizing we were nearly 4 months or less from my previously given retirement date, he was keenly aware we needed a Plan B or even Plan C. There were a few questions he asked me:

  • Was I still planning on retiring?
  • What date was I planning on retiring?
  • What flexibility, if any, did I have with that date in mind?
  • Since Apple were heading into review season, he needed to know what to do about my annual stock grant.

He asked that I have a come-back to him by end of July. I started immediately preparing answers to these questions and had prepared an email ready to be sent out but I chose to sit on it a night. The next day I decided that it really didn’t serve me to send it out earlier than he asked. My boss had started to bring up the possibility of having me stay on until April (the next vest date) and I figured having that flexibility in my back pocket wasn’t a bad place to be in.

Late July I sent out my responses to these questions in email. Yes, I am still planning on retiring and, in fact, I have become more at peace with the decision and more excited.

I had done some research on what date I was going to leave. Initially I had figured early November would allow me not only to get October’s RSU vesting but it would also allow me to get the payout of the Director and above quarterly bonus. Further research on that seemed to suggest that the Fiscal Quarter were done September 24th and best that I could tell, I’d be eligible for that payout, should Apple hit its revenue targets. So, I figured a week after RSU vesting or October 22nd would be the earliest Friday. I was starting to get worried about the cross-country drive and having the time to visit all of the people and cities we wanted.

As for flexibility, I basically told him that my home was on sale and that I were leaving California. Further, I had a fixed, unmovable schedule of dropping While One back in the water to head down the coast to Fort Lauderdale for solar installation. I told him I expect to be in the Bahamas for Christmas…and I intend to do everything possible to keep this goal.

Regarding RSUs, I told him since I already had one foot out the door, it doesn’t seem fare to take part of his RSU budget from others on the team. I told him to withhold whatever he was going to give me.

Our next 1:1 we walked through my thoughts. First, let me acknowledge how fortunate I am to seemingly be as valued as I am. I’ve either left or quit Apple several times during my tenure and each time, I’ve been met with similar responses from management.

It became clear to my boss that it’s looking unlikely that my replacement will be found and all roles and responsibilities handed off to this person in the next 90 days or so. We talked about staying on till April with some extended Flexible Work Arrangement whereby I’d work remotely for 2 weeks with 1 week in Cupertino.

At first, this seems like a nightmare scenario. However, I’ve since come around to being agnostic or even slightly optimistic to this scenario. It would be extremely tiring but easing into retirement seems to have it’s benefits as well.

We talked about travel expenses and lodging when I were here to which I was told it was not to be paid for. I suspect I could push and play hardball a bit more. To be fair, Apple’s in a bind. It’s not that I’m not replaceable, it’s just that I’m not replaceable in 90 days. That said, I have an immense amount of gratitude for Apple and everything it’s done for me. Others, I suspect, might push this a bit harder…and maybe I should, but it’s just not me.

Initial Conversations

On October 25, 2021 during my 1:1 with my boss, I told him I was “starting” to think about retirement and asked him how long does he need to know by.

Of course, I already have a date in my head but he, of course, turned my question around and asked me something to the effect of “so, when are you thinking? Is this a 1-2 year thing or a 3-5 year thing”. “It’s not 3-5”, I said.

My retirement date has been moved many times. I’ll talk about those cases in future blogs. Suffice it to say, it’s been one of the hardest decisions of my life. There’s something about the finality of it that scares the hell out of me. More on this later.

I had originally planned to have it prior to my review which, at Apple, is generally early October. October starts our new comp cycle. But, as I started to think about it, I figured I should wait until after my review just in case my mind changed and I screwed myself out of money going into my review. So, I decided to wait until my review.

My review came and went and I still didn’t broach the subject. Of course, I call it a “review” loosely because the fact is, I haven’t had an officially formal “review” of my performance written down since 2013. Most would think this as a good thing and, I suspect it is. I’m my biggest critic and most of the times, I’m already well aware of what I need to work on without being told and often times, have a lot higher bar than others. However, there is a downside in that it can be misconstrued as coming off as your manager isn’t really “investing in you” and that he/she is merely interested in having you do the great job you already do…I tended to look at it this way, whether it was true or false, I don’t know.

Anyways, my new compensation and particularly my RSUs were so strong, I just couldn’t bring it up. I think mostly because, in the back of my head, I was saying to myself: “Are you fucking crazy, why would you give this up?”

Apple has been so incredibly good to me and my family. Don’t get me wrong. They expect a lot and it’s nothing like the country club Google, I had heard rumors it to be. Without a doubt, it’s a pressure cooker. The culture is so self-fed that high performing, highly talented folks naturally feed the competitiveness of other high performing, highly talented folks. You either sink or drown and ultimately leave the company.

Of course, I couldn’t stop planning and thinking about my retirement. Our boat is coming in December. We’re starting to talk to Real Estate agents about buying a new place near the boat. I’ve shipped one of my cars to Florida. I’m starting to pack up the house, putting things in piles of “garage sale” versus “store.” I keep telling myself this is happening as well as everybody else in my life.

So, when my boss scheduled our 1:1 a few weeks out, I decided that would be they day. Following, I felt pretty normal. No new anxieties. Started to think about who my successor would be. There was one individual I worked with who had been on the short list (of one) a while ago. “When was our next 1:1?”, I asked myself.

On October 27 we had the conversation. I confided in this person my timeframe and told him that nobody else knew so to keep it confidential. This morning, BTW, I started to keep a running list of folks I’ve told whom and what to…there’s too much at stake for folks telling my story and me not controlling the narrative. He seemed pleased for me. I gave him a loose timeline of pre-Thanksgiving for feedback on interest. I encouraged him to speak to my boss.

This conversation hit me a bit harder. I kept asking myself “why?” I’m still not sure I have the answer but for some reason this seemed to be a much bigger step towards my retirement than even telling my boss. I’ve either quit or left Apple 3 times now (I’ll talk about those in future blogs because there’s a lot of good info there!). I’m not new to this. However, this felt a lot more like the ball started rolling down the hill and couldn’t be stopped…and, I guess, it really can’t. There’s no coming back to that individual to say “I changed my mind.” You just can’t do that to people. For your boss, you can…he/she will most likely be delighted.

Anyway, I had a gig with my band, Identity Problem, as San Pedro Market that night. This subject was in my mind the entire time. So much so that when I woke up this morning I decided I needed to write this.

To be continued…

You Only Get What You Ask For

I graduated from Marquette University in 1992 and at that time, the economy was rather poor. Despite all of my efforts to land a so-called White-collar engineering job, I ultimately decided to take a position at Cincinnati Microwave, a company which made the Passport and Escort radar detectors. The position was through a temp agency and my position was to tune the antenna cavities of the radar receivers on the assembly line. During that time, I continue to look for more “permanent” work.

At some point, management took notice that I actually could do far more than tune microwave antennas and I started working in the test department writing programs to automate test equipment for their fixtures. I continued to look for a more permanent position as well as trying to convince management to hire me full time. Ultimately, I found another position elsewhere and I left. Their loss.

At VL Engineering, a 3 man consultancy, I started at $26,000 a year. It was a great job, I liked working for a small company as I got to wear many hats. I really developed my programming chops and designed all types of products. However, there was no 401(k) program and, to be honest, I’m not even sure how good my healthcare was….if I had it at all. Annual raises were minimum and I received no bonus. It wasn’t until I landed a job a U.S. Robotics that he opened up his pocket book a bit more but by that time, I was already gone.

Sherine and I moved to Chicago. I received a significant boost in salary and Sherine was quickly able to land another engineering position with a similar bump. Dual income and no kids living in Chicago in our mid to late 20’s was awesome.

After several different jobs in Chicago and earning my masters, I was earning significantly more than I was in Cincinnati. Between jobs, Apple gave me a call asking if I wanted to interview. “Apple who?” I thought to myself. We decided to check it out and I flew out, had a grueling day of interviews (including Tony Fadell) and came back home with my tail between my legs. “I’m not going to get the job”, I told Sherine.

Surprisingly they did. I later learned from folks that interviewed me that most folks were impressed on how I held my composure. Who knew. Perspective is everything. Apple offered my $126,000. Looking back on this, I could have gotten way more. That was cheap.

My salary grew relatively quickly and I loved working for Apple. I was at the right place at the right time to have been given the opportunity to work on the first iPhone. I was treated pretty well at Apple but by starting salary was initially so low that the increases were modest. After a period of time, I started to recognize I needed to ask for what I wanted.

First I asked to be a lead System Integrator. Then I asked to be a manager. Then I said I was bored and wanted to do something else. That’s when I started to work on Apple Watch.

After a few years, I was burnt out and needed a change, so I quit. I had probably 4-5 weeks of vacation saved up but I needed something longer. Further, I have anxiety about running out of vacation and always need to have some “in the bank.”. It’s always been my problem, I know. I just need to know I can always escape…but yet I never do.

Management offered for me to take a leave of absence instead and, if I chose to come back within the year I’d get all of my RSU’s and seniority back. I took 9 blissful months off. It actually took 1 month to really decompress. Everyone in my family commented on how noticeably different I was and that the “old Mike was back.”

I’ve been back at Apple 9 year now and I’ve quit 2 more times. The last time I threatened to quit if I didn’t make Distinguished Engineer. I told them I earned it and I was worth it. I had been trying to hire folks of my team and I knew just how talented I was. I knew I could get another job in a heartbeat if I left. I got the promotion.

As mentioned, I told my boss I was retiring back in October. His first question was “when, 3-5 years?”. His next question was, after I said “definitely not” was, “is there something we can do monetarily.”. I told him it’s not about the money and I didn’t need to work.

I got this idea of engineering your resignation from the Financial Samurai. Of course, in order to be able to ask for these things, you have to be reasonably confident of your capabilities and your worth within the organization. There are plenty of folks in every organization that companies would be happy to let go.

We’re starting to discuss the potential extension of my retirement. My boss has suggested he’ll “make it worth my while.”. Of course, he’s not showing his hand. Our dialog is being captured in email. I have warned him, after trying to find slips in the Bahamas, that if he waits to long there will be no guarantee I’ll be able to extend my employment to help bring up my successor. Sherine will not be confident to stay on the boat anchored for a week+ every other two weeks alone. Let’s see what happens.

Regardless, I could care less one way or another. Ff they do make it worth my while, I’ll make it work otherwise, I’ve already decided to leave and the closer I get to October 22, the more excited and at peace I am with the the decision.

Time to make it Worth my While or adios.

The Perfect Storm

This is a delayed post written on September 28, 2022.

Ian is hours from making Landfall on Southwest Florida and over the top of my Father’s house that I have recently purchased from my sister. The Market in Bear market territory. The housing marking contracting and well off its peak and, of course, the threat of Nuclear war from the egomaniac Putin. Yes, this seems like a Perfect Storm for anxiety, worry and angst for almost anybody, let alone someone quickly approaching retirement! The nagging question of “What are you doing?” is like a 90dB siren in my head.

As I sit contemplating this, I figured there’s a lesson in this somewhere although I suspect I’ll have to circle back on this post in 6 months or so with my learnings…

My retirement has been in the works for nearly a year since I first gave notice to my boss. At that time, our investments were near their peaks. Our property had never been appraised higher. The economy was firing on all cylinders. It seemed like the stars and the sun aligned and this was the perfect time to make such a transition. This is not something Sherine and I took lightly. We’re planners. In fact, we’ve been planning this event for many years and the date has been moved at least twice, if not more. Of course, we had been working toward the goal of retirement for 30 years or more, socking away money anywhere we can and investing it smartly.

I recognize that even with everything going on, I’m still very fortunate. In the words of Joe Walsh, “I really can’t complain, but sometimes I still do.”. I’m human after all. I could be better, I know this.

At the end of the day, in the mist of a Storm like this, it’s easy to jump to conclusions quickly. My house, that I just replaced the roof on, will have it’s windows blown in and the house will be flooded. Ian will continue up the coast and cause mass destruction up in Virginia where my boat is sitting. The market will continue to drop 40% and the housing market will completely collapse with 10% mortgage interest rates. Follow this with large-scale deaths due to Nuclear war and a un-rest in the United States due to our ridiculous left and right wing politicians. Yeah, it can get a LOT worse.

But, I have to remind myself that I’m spinning out. I can’t control these things and even further, the likelihood of ALL of these things happening is likely just as unlikely as winning the lottery. At least this is what I hope.

I don’t know what the lessons will be from this. However, I do know this. Firstly, Sherine and I do not make rash decisions. They’re well thought out and we belabor over the smallest of details. Secondly, life is so short. Having just lost another friend to cancer at age 52, I am repeatedly reminded of this. At the end of the day, we’re going to be OK and it’s only money. Lastly, Sherine and I have a very strong marriage and at the end of the day, we’ll have each other.

Finally! We’re Moving Out Today

We’ve literally been packing this house since March. The POD is fully packed…and I mean FULLY but somehow we still have to find room for another half-dozen items or more. We were unable to bring our bikes and a few other items so I guess we’ll be hauling them to Virginia and storing them until June when we sail back to haul While One out.

It’s a little surreal. I’ve been working towards this day for probably a decade or more and to finally see it come to fruition is a huge pile of emotions. I thought I’ve feel relief by now. Perhaps it’s due to lack of sleep. I can’t remember the last time I’ve slept through the night and the past handful of days, it has spread to Sherine as well. I’m excited to do something new yet, at the same time, sad to see this chapter of my life done. Scared that I’m making the wrong decision. Worried about everything that’s going on in the World and in the United States.

The sorting, selling, packing, giving away and moving stuff from one room to the next, to a storage room and back to the house and between storage rooms has been exhausting. We have probably dozens of man/woman days invested in this move and we’re not quite done. In December we have to unload the pod and try to make our new house a home. We have a storage unit in Sarasota because, let’s face it, the 900 sq. ft. house we’re moving into isn’t going to come close to holding our stuff…even after splitting it between long term storage with JK Moving and our boat. I’m trying to live in the moment and appreciate this for every minute…I’m not likely to experience anything like this again in my lifetime. On the other hand, when I’m finally at anchor or at a marina in Bimini in December, that’s when I think it’ll all sink in.

Yesterday evening my retirement was communicated to the greater Apple Watch System team. It was emotional…I expected it to be so but even so, it’s hard to prepare. Looking at a picture shown taken at the factory with iPhone ready to be shipped…a few more pounds, a lot more gray, less hair on my head and no beard. It was a great time. Apple’s been so good to my family and I and I’ve been so fortunate to have had the opportunity to work on two highly successful products that have literally changed the world.

10 Days to go and we’re closing up the door on the U-Haul trailer and heading cross-country.

You don’t have to go too long these days…

As of today, we’re about 53 days away from closing up the U-haul and starting our epic journey across the country. It’s going to be fall. We’re excited for the open road, seeing friends and family, lots of time to talk and hopefully we’ll get some fall leaves.

Even though the days and moments that I doubt my rationale for doing what we’re doing are fewer and fewer, it seems I don’t have to go too long these days to be reminded of exactly why we’re doing this in the first place.

On Saturday, Sherine reached out to an old co-worker from years ago to tell him of our plans. He then told us of how he had retired some 10 years ago, before he actually had planned, due to unexpected changes in his life. Long story short, he had 9 blissful years with his wife before she was diagnosed with and had died of a rare cancer within a year. There was not a bone in his body that questioned what we were doing. This story is getting all too familiar.

Then, we learned of an old friend from college loosing her battle with cancer. She’s in Hospice now and it seems, from what we’re hearing, she’s not likely to live many more days…if not hours. Even though we’ve lost touch over the years, its still hitting us, but mostly Sherine, really hard. “It’s not fair” Sherine says. She’s so young and was so strong in her days when she wasn’t sick. It’s depressing to think of all of the friends we’ve lost to cancer over the last decade.

Anyway, it seems that I don’t have to go too long these days to be reminded of why I’m doing this. With every checkup at the various doctors that Sherine and I have been going to in anticipation of us changing residency, we hold our breath just a little bit longer and breath a sigh of relief when we get good news…but, I know that’s not guaranteed to last and so, this is why we’re doing what we’re doing.