Trailblazer's Journal

Where are you and where are you going?
trailblazer
Posts: 77
Joined: Sun Jan 03, 2016 8:18 pm

Re: Trailblazer's Journal

Post by trailblazer » Sat May 12, 2018 6:49 pm

2Birds1Stone wrote:
Sat May 12, 2018 7:24 am
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
Posts: 77
Joined: Sun Jan 03, 2016 8:18 pm

Re: Trailblazer's Journal

Post by trailblazer » Thu May 24, 2018 10:07 pm

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
Posts: 42
Joined: Fri May 04, 2018 1:49 am

Re: Trailblazer's Journal

Post by thegreatvoid » Fri May 25, 2018 12:20 am

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
Posts: 238
Joined: Thu Nov 19, 2015 11:20 am

Re: Trailblazer's Journal

Post by 2Birds1Stone » Fri May 25, 2018 7:25 am

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

trailblazer
Posts: 77
Joined: Sun Jan 03, 2016 8:18 pm

Re: Trailblazer's Journal

Post by trailblazer » Fri May 25, 2018 11:24 pm

@the great void:

Good questions.
thegreatvoid wrote:
Fri May 25, 2018 12:20 am
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.
thegreatvoid wrote:
Fri May 25, 2018 12:20 am
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).
thegreatvoid wrote:
Fri May 25, 2018 12:20 am
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
2Birds1Stone wrote:
Fri May 25, 2018 7:25 am
Well this journal took an interesting turn.....life doesn't have to be all or nothing ;)
:D 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
Posts: 77
Joined: Sun Jan 03, 2016 8:18 pm

Re: Trailblazer's Journal

Post by trailblazer » Fri Jun 22, 2018 11:43 pm

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
Posts: 238
Joined: Thu Nov 19, 2015 11:20 am

Re: Trailblazer's Journal

Post by 2Birds1Stone » Sat Jun 23, 2018 6:53 am

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
Posts: 77
Joined: Sun Jan 03, 2016 8:18 pm

Re: Trailblazer's Journal

Post by trailblazer » Sat Jun 23, 2018 10:34 am

2Birds1Stone wrote:
Sat Jun 23, 2018 6:53 am
How much is rent?
Since my goal is to be more transparent I guess I have to answer. :D

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

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

trailblazer
Posts: 77
Joined: Sun Jan 03, 2016 8:18 pm

Annual Book List Part 1

Post by trailblazer » Fri Jun 29, 2018 8:19 pm

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. :D ).

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
Posts: 77
Joined: Sun Jan 03, 2016 8:18 pm

Re: Trailblazer's Journal

Post by trailblazer » Wed Jul 11, 2018 11:36 pm

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++
Posts: 782
Joined: Sat May 23, 2015 3:46 pm

Re: Trailblazer's Journal

Post by thrifty++ » Thu Jul 12, 2018 6:59 am

trailblazer wrote:
Wed Jul 11, 2018 11:36 pm
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!

trailblazer
Posts: 77
Joined: Sun Jan 03, 2016 8:18 pm

Re: Trailblazer's Journal

Post by trailblazer » Sat Jul 14, 2018 8:46 pm

@thrifty++ - thanks good reminder! Yes next couple months are going to be key I think in terms of taking the right kind of risks to set myself up for a life as a freedom enjoying entrepreneur vs. well paid but dispirited wage slave. I respect and like the people I’m working with so don’t want to be a jerk but also need to be a bit more agressive in certain ways.

Speaking of freedom . . . Just spent the last hour reading the new blog from infamous pharma bro Martin Shkreli www.martinshkreli.com who is blogging from prison (he is serving 38 months for securities fraud). Mix of high intelligence, deep expertise (in his case biotech), personal resilience and unrepentent sociopathy. Not too much content yet but I will be checking in on him from time to time! Basically it’s a bunch of random snippets: 60% about biotech (very technical) combined with random comments on prison life, pop culture, politics, how society screwed him, etc.

One of his more amusing struggles is he needs to get a form notarized to cash in several million dollars of stock options, but the prison only has one notary so it’s been hard to get the form completed.

This quote reminded me of things ERE people say about work and early retirement :D “The 13th is my favorite day of the month, as I was remanded on the 13th and it’s easy to count the months. I have about 3 years left exactly. That I’ll spend 5% of my life in isolated study isn’t pleasant but books like Frankel’s “Man’s Search For Meaning” puts things into perspective! Everyone said the biggest downside to jail is boredom. I am not bored… very, very far from it.”

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