Trailblazer's Journal

[niemand]

LOL, in my last lucid dream I did an internet search for a passport sleeve and found exactly the design I needed. While dreaming I thought "I really need to remember the brand name". After the dream I woke up briefly, wrote down "karamaback" before sleeping some more.

Very handy indeed if dreams allow you to unearth existing information from you subconscious.....

Next day, although it hadn't occurred to me before that I needed one, I looked for karamaback passport sleeves online. It made sense, I just had gotten a new passport and the old one was falling apart after nine years of use ....

Of course the brand "karamaback" didn't exist at all.
Damn you subconscious!

So I went with the ERE solution of having no passport sleeve at all. They expire after 10 years anyway, and getting nine years out of them is pretty alright.

[chenda]

karamaback sounds like a good name for some high end business

[trailblazer]

I deliberately try to go to bed as late as possible to make that [awake] period as short as possible, but maybe I shouldn't.

You could try it a few times and see what happens. For me, it ends up being a useful period of clarity. I get out of bed, say "well i'm awake now" and sit in a chair. I'll read, maybe get up and do an easy chore.

When I was still working, I found it was a good time to draft emails that I had previously been stuck on . . . once or twice sending them at 3 a.m. for fun. In general, it's a good time for getting unstuck on decisions.

I try to avoid anything too random - like checking headlines or something that isn't substantive (like listening to music). I will have a few sips of coffee. I usually think to myself "I'm up for good now" but after a few hours the fatigue hits and I'm back asleep. Maybe 20% of the time I don't fall back asleep - usually I can explain it - too much coffee, got too involved in reading messages. I then fall asleep earlier the next night.

Very handy indeed if dreams allow you to unearth existing information from you subconscious.....

haha. that's about as useful as my dreams have been so far, too. But there must be some reason we have them, right?

[trailblazer]

I’ve decided that my ideal life will be:

1. 3 to 6 months extensive travel
2. 3 to 6 months sit home and do nothing
3. 3 to 6 months intensive work
4. Repeat over and over

I’ve just checked off items 1 and 2. That means . . . it’s time for #3. As a result, I’ve joined a start-up!

The subject matter itself is somewhat meh [a lot meh], but the underlying business model is disruptive to established companies in my prior industry. I happen to know that my former mega corp employer is aware of what we are doing, has expressed concern/interest, and that they are not in a position to rapidly adapt. All of this makes my contrarian heart feel happy.

The role itself will be a stretch role - building on existing skills and requiring development of a range of new ones. Sadly not true renaissance skills like carpentry or wilderness survival, but it will build and broaden my business acumen, making it all the easier to get interesting gigs down the road.

I will receive a modest salary - it will cover ongoing living expenses and benefits with room to spare. Most of the surplus will probably be spent on purchasing consumer conveniences to make the intense workload easier, though I may dabble in a few riskier investment strategies I've been wanting to try but can't justify within my existing retirement nut [microcaps, options, and a bit more crypto when prices dip].

Within 3 to 6 months, it should be clear whether this has any legs, both the business itself and my personal involvement. I know the team well and it will be fun to work with them. Lots of start-up horror stories out there, so hopefully we all survive intact. But bottom line is I’ve been getting the urge lately for a “give it all you got/be all you can be/[insert other cliche here]” opportunity.

[wolf]

2. 3 to 6 months sit home and do nothing
I’ve just checked off items 1 and 2.

Although I understand the idea about a balance in lifestyles, I am somehow afraid by sitting at home and doing nothing. If it wouldn't be meaningful, I wouldn't do it again. But I would try it at least one time.
So, how was it?

And I wish you good luck at your new job at the startup! (also something I wanna do once in my life)

[trailblazer]

Thanks Wolf - I'm excited to try being on the start-up side of the fence.

Of course I didn't literally do nothing at home. More that it was a nice contrast to the unsettled feeling that creeps in after traveling. It was a good time of 1) generally doing whatever I felt like; 2) resting up (both from the travel and to some extent my prior job); 3) getting diet/fitness on the right track (a very big priority); 4) tons of time for reading and reflecting, local trips/hikes, etc.

Probably the biggest outcome of my time at home was a good sense of both future priorities and also building "core" personal disciplines (especially health) that I want to maintain no matter where I am in the cycle. I'm on a good trajectory now and am relatively confident that I can keep doing the right thing even while working.

So probably a more precise future cycle would be:

- 4 or 5 months slow travel
- 3 to 6 months home (leaning toward 3 months), generally doing whatever I feel like but also having some sort of "personal improvement project" that is best done while staying in one place
- 3 to 6 months some sort of work gig

[thrifty++]

Hey awesome that you have retired early ! and take some time to relax. With a nice big FU stash.
I also have very much enjoyed reading about your startup opportunity coming up and you having the flexibility to take it up without worrying too much about money. Thats what its all about right, having leverage and freedom to pick and choose from options. I'd like to hope I will be in a similar situation to you at some point. Maybe in a couple of years.

[trailblazer]

@thrifty++ - thanks - really appreciate it! It's all about having flexibility. Cool to read about the sabbatical you are taking (I think I read that somewhere).

3 weeks in with the "full time" work. A few random observations in no particular order:

I was feeling very unconfident the first day. I still have trepidation about any number of tasks - especially things I’ve never done before, or things everyone assumes I can do but I have never actually done - but in general, a sense of momentum and confidence is returning. That had atrophied while I wasn’t working. The nature of the work I’m doing means I’m constantly being thrown into problem solving situations. It is very stressful but I think this is a good thing. I’m sure I would score far higher today on some sort of cognitive problem solving test than I would have four weeks ago. Quite a bit of politicking - uggh i just want to be alone and read a book - but it's good for me to get better at this.

I never did a great job when working full-time of managing anxiety/stress about work with maintaining a sense of balance outside of life. My goal with this current working phase is to learn to maintain a calm mental state while working and under lots of stress. I think this is going to be key to a successful life. People who are "successful" are essentially managing to function while in a high stress situation. Life will never be perfectly buttoned down, and if it is, it might not be the life I want.

I’d be perfectly happy to get this stimulation in a non-work situation, but I haven’t found an equivalent outside of work. I guess this is why people have kids - gives them friction they have to work through and thus builds character.

Although I probably sound stressed out based on the above paragraphs, I'm actually 100% convinced that I will never again work in a traditional corporate setting. So much more satisfying to be on the entrepreneurial side of things. I feel a real sense of ownership in what I'm doing now. Despite the above, I'm actually excited to see how this all plays out. Still feeling good camaraderie with my co-workers.

I don’t like having money in qualified retirement accounts. I do like the fact that I can trade stocks freely without tax implications. But overall, I like the money in my brokerage better. In theory there is the Roth pipeline, but I wonder how many low wage years I will really have between now and age 59. If I have a low wage year in the future I might just cash out the 401k and pay the 10% penalty.

I now have $40K of crypto - yikes. The modest income stream I'm now enjoying has made me more aggressive about buying on dips.

I’ve still had quite a few longer/deeper dreams since I started working again. I wonder if that will start to fade. Time spent reading has gone down dramatically.

For those wondering about whether they should take a year or so off, and what might happen to their career, I can assure you, it is no big deal. People think it's cool that I took some time off to "travel" (frankly, they don't really care, they say "oh cool a year off to travel"). It has not hurt me at all career-wise. I'm sure a longer gap would start to hurt, but i think a year off can be easily justified to people, especially if you are mid-career.

[2Birds1Stone]

I'm very appreciative of your journal. It's awesome to hear that your first 2 phases of an ideal life went well and phase 3 is off to a good start. So, do you still see yourself giving this up after another 4-6 months and repeating phase 1-2 again?

Seems like this approach will never have you tapping your portfolio, so long as you are able to replenish that "transition fund" you had lived off of before the new year.

[trailblazer]

So, do you still see yourself giving this up after another 4-6 months and repeating phase 1-2 again?

Seems like this approach will never have you tapping your portfolio, so long as you are able to replenish that "transition fund" you had lived off of before the new year.

A very good question. I think one of three things will happen:

1. We have one big customer right now. This is what makes us excited about what we can achieve, and this is also what is funding my salary. If it goes well, and if we can leverage our approach to other customers, I'd be a fool to jump ship in the next 6 months.

2. It's still very possible that things will die down with the current customer, and in that case, the decision will be made for me. Time to start booking some slow travel somewhere. Probably SE Asia since I've never done that, but I want to do another extended trip to Europe.

3. Also possible that things just go okay, in which case, I'm basically just working full-time again. In that case, I think I'd be looking to shake things up. Maybe find something else entrepreneurial. Maybe just another break. I like having something entrepreneurial in the works. I don't think I want to give that up completely. I also find that it's a really satisfying form of socializing. Be friends with the people in part because you are working on some sort of business idea together. I love the group I'm working with and hope I can always be trying some sort of business with them.

Financially, I feel like I have enough to have basic security. Anything in the mid- to low- 300K range is good enough in my book in terms of net worth. I could see myself replenishing my cash account, spending till I'm down to around 300K, then finding some more paid work.

[trailblazer]

I’m not a big fan of John McCain - I actually can’t stand him - but I admire how he has absolutely pushed himself to the very end. Giving life everything he’s got until death by brain cancer intervenes. He could have retired years ago in total luxury.

I’ve had this vision from time to time of pushing myself completely to the age of 70 and then holding on for dear life in one final push. It’s tempting to stop and rest but I think it’s best to push myself.

Five weeks in on my return to the “real world”. I’m excited about my situation (and also stressed out about it). The people I’m working with are all about 5 years older than me and are all more “successful” than me in terms of career, money and social skills. On the one hand it’s a bit intimidating. They are better than me at the game of life. There is no other way to say it. They are just better at it. I’ve always done well at school and good enough at the career game, but I feel like I’m playing with the kids who beat me.

At the same time, one of the current cliches of self improvement is that you are the average of the 5 people closest to you. In that case I will soon be enjoying lots of personal growth.

I think I’m going to spend the rest of my life working unless I can find some sort of other “real” replacement for it. For the rest of my life my goal is to be “risk on” in terms of career, social, etc. It’s so tempting to want to stop and rest, but I also have this vision of completely pushing myself until I’m about 70 and then seeing where I’m at. Push myself all the way to the finish.

[thegreatvoid]

Why work yourself into an early grave ?

Do you have children or plan to have any ? If not, why work for the benefit of a future society that you are not invested in.
Legacy ? Most of us will be forgotten within two generations

I dream of the day the gap between men´s and women´s life expectancy will be closing.
It´s not going to happen as long as men think they have to be the workhorse for a society that doesn´t appreciate their sacrifice.

[2Birds1Stone]

Well this journal took an interesting turn.....life doesn't have to be all or nothing

[trailblazer]

@the great void:

Good questions.

Why work yourself into an early grave ?

I would say the goal is to avoid an early grave by living a life that has a certain amount of unpredictability and dissonance that requires creative problem solving. Any “voluntary” work should be roughly aligned with my strengths and be with decent people. Dropping dead at my desk of a heart attack at 52 while being screamed at by a boss would not be a successful implementation of this plan.

Do you have children or plan to have any?

No and no. I like to say “I want to take risk” but I don’t really mean it. I don’t think there is any real harm that can come from something like losing a job. If I really wanted to test myself I would probably have a kid because that would be the ultimate test of unpredictability and risk, and a test that you can’t bail out on (and that is probably a very bad reason to have a kid).

If not, why work for the benefit of a future society that you are not invested in.
Legacy ? Most of us will be forgotten within two generations

I agree. Legacy seems like a fragile thing to strive for, and as you point out, we will be gone anyway.

It’s a combination of 1) the Teddy Roosevelt “man in the arena” idea; 2) getting closer and closer to the “mid life” crisis years and a sense that while I’ve done okay in life I’m capable of more; 3) I’ve actually been having fun lately engaging with people; and 4) my life is unbalanced.

The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly

Well this journal took an interesting turn.....life doesn't have to be all or nothing

yeah I guess it won't be shocking when I post in 6 months that I’m taking a break. At the moment I’m having quite a bit of fun and feeling the right amount of stressful challenge. My life is unbalanced though. My web of goals is quite strong in many areas but pretty undeveloped in others. In the near future I want to focus on becoming more balanced while navigating the stress of work. Seems like a good challenge to try and pull off and is something I've never fully achieved. The first step is to figure out what I even mean by the word "balanced."

[trailblazer]

Time for a quick update. Half way through bottle two of wine on Friday night so why not. One of the original goals of the journal was to be “transparent” . . . I am by nature not transparent so I’ll try to work on that.

Current net worth is 325K. 10K of crypto loss plus way too much spending moving to an apartment in downtown SF - thus I’m down a bit from prior updates. But still HODLING the crypto - all the way to zero - and the apartment is fantastic. The start up adventure continues to go well. Our client #1 is paying and we actually want to dump client #1 now as clients #2, 3 etc. look even more profitable. My goal is to push to $400K net worth and then re-evaluate. So far having fun (or I should say stressful fun) and drawing about 9K net a month from client fees so should be able to get there within a year or so. My entire social life is work-related so may as well earn some money. Goal of the start-up is to be bought out by a bigger firm in about 5 years and draw a decent income in the meantime.

My driver’s license just expired. I’m tempted to not renew. My minimal transport needs are served by Uber and I live right next to work and groceries, so I’ve achieved 2 out of the 3 ERE trifecta. Proud to say I have a perfect 100 walkscore in the heart of SF. I just learned California DMV requires 6 weeks wait for an appointment so I will have a chance to try life without a driver’s license. I love road trips but I also think driving is a massively expensive and risk-filled activity. I also noticed that the airport security people don’t seem to check whether license is expired, so one less reason to renew.

Just had a big milestone birthday. Goals for the next year (6/30/19) are:

Hit 400K net worth
Lose 30 pounds - this will get me to a good spot
Do 3x/ per week strength training routine, every single week
Read 52 books (1 per week)
Read through Bible 2x (ughhhh childhood guilt from parents combined with genuine belief that this is a worthwhile endeavor - I’ve read it 1x per year for the last 5 years or so - yes I am a conflicted person)
Read through about 10 other books that I’ve put on my “personal annual canon of great books that I read every year” list. I should probably do a separate post on those books at some point but they include the books that I read annually - books I want to exemplify in my life. Some of the better known ones are: The Effective Executive; The Black Swan; The Fellowship of the Ring; Fifth Business; Canticle of Leibowitz; Tell It Slant plus some random things I’ve read over the years that have stuck with me and been examples of “the person that I want to be in life.” I’ve done this for the last 10 years or so (ever since my last milestone birthday) and I do have to say that the books have started to become a part of me.

And just got an email from an old acquaintance/friend/person I am in love with who will be visiting in a few months. Hmmm will be interesting. They sent the email through a social media site I haven't checked in months but just happened to look at. All very interesting . . .

That’s all for now.

[2Birds1Stone]

Nice update, maybe you should be required to drink at least a bottle of wine before posting here?

I like the goals, that's a shit ton of reading! I read way too much online and not enough books, but this year has been my best since finishing grade school.

Being in a walkable location is so awesome. I enjoy the shit out of it when we go on short 2-3 day vacations to fun cities a few times a year. Long Island is NOT walkable, and biking is doable but dangerous in most places near me. How much is rent?

The definitely do check your documents for expiration when you travel, even domestically. I would double check so you're not stuck in a hard place when you need most to get on a plane somewhere.

[trailblazer]

How much is rent?

Since my goal is to be more transparent I guess I have to answer.

Tempted to first write 17 paragraphs rationalizing why it's not as bad as it seems but that would be a weak move.

It's $3,200 per month. (But no car! no car!)

[trailblazer]

In grade school a boy in our class had chronic health issues and never attended. His mom and my mom were good friends. They decided I would be his “friend” to help ease his loneliness. (This was zero percent a good deed on my part - I complained non-stop until I was allowed to quit being his friend.)

Since we couldn’t meet in person due to his health, every afternoon he would call and tell me about the cartoons he watched. I didn’t watch the same cartoons, and he had a bad stutter, so I had no idea what he was saying. But he was always enthused as he raved about each cartoon. He would go on and on. After 30 minutes (she timed it) my mom would stand next to the phone and yell “it’s time for dinner!” so I could hang up.

This series of journal entries will kind of be like that - me going on and on about the books I like.

****

I mentioned before that I have a short list of books I re-read each year. I’ve done this for 10 years now, trying to add one book per year to the list although a few times I never found one worth adding.

I have 7 books on the list (two are actually recorded lectures) plus a handful of movies. This year I’m going to write a review of each book as I read it (I always think of June as the end of the year due to endless fiscal years at prior employers, school year endings, etc. ).

This practice was inspired by C.S. Lewis’s idea that a good book is a book you re-read. Any book from any genre can be “good” or “literary" if someone values re-reading it, although some types of books are probably more likely to be re-readable.

In high school I was addicted to John Grisham books but have since found that I can’t get past page 5 when trying to re-read. Maybe some people out there love meditating on John Grisham but for me it was just a moment of entertainment / escapist fantasy. And many books are rewarding to revisit, but once a decade is plenty.

If I read a book and like it, I’ll try to re-read it at some point. (C.S. Lewis recommended 2 re-reads for every new book you read - I don’t quite achieve that but I’m around 50/50.). I find myself starting to think back to some of these books and reflecting “this exemplifies some aspect of what I want to be in life.”

Very few books hold up to an annual re-reading. The book has to resonate with you personally - it can’t just be someone else’s “classic.” But for the few that do, I find myself looking forward to the story and anticipating the best sections. The books start to serve as a frame of reference when reading other books and actually become quite comforting. No matter what happens in life over the coming decades I’ll still be revisiting these same ideas 50 years from now (if I’m still here!).

Lately I’ve also started thinking more about some of the common themes I’m attracted to. For example, I definitely have an individual (as opposed to collective) mindset, and this is reflected throughout the list, or at least for what I pull out of each book. I’m also a sucker for “back against the wall” type stories where someone has to make a decision about what they truly value in life and make a leap of faith against all reason.

So with that, during July I’ll be reading, and reporting back on . . . A Canticle for Leibowitz by Walter M. Miller Jr.

[trailblazer]

I’ve been working full time for the past 3 months but in a much more entrepreneurial environment than my prior megacorp job. Almost every day has been a back and forth mood of complete insecurity and fear vs. excitement to be pushing forward. It is definitely a stretch role . . . I have yet to feel like I know what I’m doing.

I’ve decided this insecurity is pathetic. I have just enough saved up that I’m set for life - at least in terms of basic survival. I need to be more aggressive. We have one main client that has been paying the bills and lately I’ve been trying to be much more proactive and bold in what I recommend to them rather than cowering in fear that I will upset them. I’ll let you know how it goes . . .

Looking ahead, I’m thinking of trading some of my current “draw” for additional equity. The guys I’m working with are much wealthier than me (like 30-50x more) so they’ve been content to let me have a pretty generous share of the immediate client fees. I could probably continue like this for years and accumulate an attractive net worth. But if I’m going to do this hard core I want to have a meaningful stake. But I also like the idea of quitting in 6 months and traveling, in which case immediate cash is nice . . . so conflicted . . .

I don’t like weekends. The anxiety builds up, but once I’m in the middle of the workweek (like I am tonight!) the anxiety goes away.

As for annual goals, I’ve managed to get in quite a bit of reading. As noted in the last post, I’m rereading Canticle for Leibowitz this month. I read it every year. You could call it sci fi but that’s misleading.

The novel begins in a monastery in the American Southwest desert 600 years after a nuclear holocaust destroyed human civilization. A group of monks goes about their business, preserving the “memorabilia” - scraps of documents from 20th century humanity - such as scraps of ancient algebra textbooks that survived the “flame deluge” - the great nuclear war in the 20th century - and the subsequent purging of all intellectuals and scientists - including their books - who are blamed for the nuclear holocaust.

Over the centuries the monks live a rather pointless existence, making copies by hand of any “memorabilia” they can find from ancient humanity. Much of the novel is about a monk that spends his life making an illuminated (artistically embellished) copy of a single engineering blue print by hand. He has no idea what it even is, but he knows it is a remnant of a prior civilization and that it was created by the founder of his monastic order - thus it is worth preserving.

My goal this year is to write a review of each of my favorite books - I’m 2/3 of the way through this one and still trying to put in words what I like about it.

[thrifty++]

I’ve decided this insecurity is pathetic. I have just enough saved up that I’m set for life - at least in terms of basic survival. I need to be more aggressive. We have one main client that has been paying the bills and lately I’ve been trying to be much more proactive and bold in what I recommend to them rather than cowering in fear that I will upset them. I’ll let you know how it goes . . .

Yes you have a fuck tonne of money now. Just remember that leverage you possess when you are lacking in confidence. I call on this leverage in my mind often in various situations - my NW is about half yours. Thats what is all about. You possess much bargaining power and it is smart for you to make ballsy moves. Realistically even though you are not financially independent in the city you live - San Fran or wherever- you likely are in many other parts of the world including some US cities, if you can live frugally enough. I cant wait to be $400k NW! Thats sweeet!