Ask James: How to Change Careers, How to Disappoint, Do I Follow My Own Advice, Is the Market Rigged, and More

(I was frustrated, like this girl in “The Perfect Drug”, painting by Brian Horton)


ALHolm ‏@holm__: can u pinpoint an event that changed you into the person you are today?


Yes.  I was depressed because I had just spent twenty years or more trying to make everyone happy. My friends, my family, my bosses, my investors, my colleagues, my employees, my customers, girlfriends, people I wanted to do business with, people I wanted to kiss up to because I thought I would benefit in some way. And it wasn’t working. At some point you have to step back and say, “this plan that I’ve had my entire life just hasn’t worked”.  Every media outlet seemed to be closing to me. Nobody was investing money with me. Every business I was trying to do was getting stalled at the gate. I felt bad about myself, like I was always trying to please but nobody was very interested in pleasing me.

So I decided to choose myself. I stopped worrying about the distant future or regretting the past. I stopped paying attention to people who blamed me or wanted something from me. I only would do what I WANTED to do. I only would be with people who I loved and who loved me. I only would work for things that I hoped would deliver real value.

By choosing myself I finally started writing a blog. Previously I had only written in places that “accepted” me. Now I accepted myself. I wrote whatever I wanted, and ultimately wherever I wanted.

And that led to new friendships, that led to an increase in my search for wellness and spirituality. It led to living a healthier life. It led to less stress and more positive people around me and more ideas flooding to me. It led to more people trying to do deals with me, asking me to participate in more activities. I started having fun for the first time in maybe 17 years. I feel this blog and everything and everyone that has connected to it has changed my life completely. I’m infinitely grateful for the changes.

And if I had to pinpoint, I’d say it was when I totally gave up on everyone and every thing. When I started to be quiet to all opportunities on the outside and choose myself first. This changed my life.



Michael Tefula ‏@michaeltefula: would you ever go into a career knowing you had a very very low chance of success? How would you prepare for it financially?


Every change is scary. Entering into a new relationship has a low chance of success. Starting a new job. Moving states. Going into a meeting with new people that you have to convince to like you. I get scared of every new thing I have to try. But how many times does one change careers in life? More than you would think? How many times do we take the plunge, do we jump off the building not seeing the net that is waiting there to catch us. The net is always there. We just can’t see it the moment we jump.

One time I switched careers. I wanted to go from being an Internet investor (which hadn’t worked out well for me in the 2000-2002 period and I went broke) into daytrading and hedge fund investing.

My chances of success was slim to none. But at the time I loved it. I wanted to do it. I was getting too depressed going broke and losing my house. I had to get off the floor and do something. There are always ways to increase chances. Every day you can do something new to increase chances, to lay the groundwork. I’m envious you get a chance to ride that steep learning curve. It’s a beautiful roller coaster.

A) First off, live a healthier life. This doesn’t mean just food. But use to track tiny improvements in these four categories: physical, emotional, mental, and spiritual. For me this meant: going to sleep earlier, stop drinking, eat better, waking up earlier, take long walks. On the emotional side, I cut off all ties to anyone negative. This was hard to do. One time I had to hang up on my parents, who were upset at me. Six months later, before I had a chance to talk to them again, my father had a stroke. I heard about that and went to sleep that night in great pain, knowing that I would never talk to him again, and the prior six months were my last chances to speak to him and I never used it. Sometimes bad things happen.

On the spiritual side I began to meditate every day. Even if it was just for five minutes. I needed to clear my head of all the fear and anxiety that had built up. It was like a steam valve. I needed to let out the steam. And on the mental side, I started to write down ideas every day. Ideas of things I needed to learn, people I needed to network with, ideas I had for trading systems. And so on.

Living a healthier life is the most important way to increase your chances but the next steps were almost as important.

B) I probably read over 200 books on investing. I read books by or about every major investor: Warren Buffett, George Soros, the “market wizards” series, any books about traders. I read about daytrading techniques, options trading, arbitrage techniques, value investing, fixed income investing, I read about M&A deals that went bad, that went good, I read about convertible arbitrage, I read about the psychology of trading. I read everything twice. I must have read at least 100 books before I started trading even one dime.

C) Community. I started participating in message boards about trading and investing. I reached out to the writers of books I enjoyed and began dialogues with them to learn more. I started meeting other investors for coffees just to learn more about their lives, their jobs, their techniques, their lifestyles. I began to “network”.

D) Software. I knew how to program. So I downloaded every tick of stock market data from 1950 on. Every stock. Every market index. And I started writing software that looked for patterns. For example, what happens if the market goes down 4 days in a row. What happens if a stock opens up 20% down on the day after earnings day, etc. I probably wrote over 500 programs. Then I started showing other people how to program the way I was so that we all began sharing patterns.

E) Trading. I needed to trade to make a living. I had no money. My expenses were outrageous. I had no excuse for such expenses except that during the internet boom I mistakenly decided to live like a drunken rock star. Now I had to survive and I did it by trading the systems I had programmed. And using the techniques I had read about to help me set position size, deal with the psychology, diversify with different techniques ranging from arbitrage to short-term to value.

F) Ideas. I started writing down ideas for articles I wanted to write. Jim Cramer liked my ideas and I started writing for and then the Financial Times and then I did a bunch of books on trading.

G) Networking more. Since my track record was getting good I started sending it out to other hedge fund managers. More and more of them started giving me money to trade, which I did successfully until I decided I didn’t want to trade anymore but I knew enough about hedge funds that I converted everything I was doing into investing into other traders and I started a fund of funds.

H) Downsizing. I knew that it could take years before I saw significant results from my new career. So I sold/lost the apartment I had been living in in NYC and went into a self-imposed exile about 70 miles north. My expenses were reduced by about 80%. I could breathe again. And in that new freedom, I could explore.

Every step of the way I reduced the risk that I would fail. Ultimately it came full circle. I was running a fund of hedge funds that was paying my income, plus I was writing and doing well and then I decided to get back to my Internet roots so I built a website that I, as an investor, felt was more useful than any other investing website.

It’s when you combine two areas that you’ve mastered and fallen in love with that you end up creating something unique that nobody has done before. Your own baby that can grow and thrive with your love and passion behind it. I did it and it was profitable from day one and then I sold it when it had millions of unique users a month. I was proud of it.

It’s through passion and love that you minimize your risk. But that only takes you to the bridge that will take you to your new career. Ultimately health, and massive preparation, reading, learning, networking, self-education, sacrifice, and actual experience will bring you across that bridge to your career.

From beginning to end when I decided to do this new career it took me: 2 years before I was making a real living and about 6 years before I can say I was VERY successful at it. I think this is a good rule of thumb. If you want to change careers and you put in the work and preparation then expect at least one year before you are making steady money, and 2-3 years before you are making a living, and you have to stick with it for 5-7 years before it starts being a big success. I’ve done this four times and I would say this rule of thumb has been true each time. For instance, in 2007 I started angel investing and I can attest that after doing all of the above it is only now I am really starting to see the results of that.



: why and how did you stop drinking?


One time I was single and on a date. We went to some bar and I started drinking. And drinking more. And drinking more. I was very funny. I had the bartender laughing and refilling. I had everyone around me laughing. The girl I was with was laughing. “You’re so cute when you are drunk!”

About halfway through I remember staggering to the bathroom and the room was spinning. When I came out of the bathroom I vaguely remember the girl kissing someone else. I vaguely remember  leaving the place and falling  on the ground around 3rd avenue and 47th street at about two in the morning in the middle of the street. Cars were honking and skidding around me. It was raining. I don’t know why a car didn’t hit me. Someone, the girl maybe, pulled me off the street and onto the sidewalk. We were all laughing while cars skidded around, avoiding me lying in the middle of a busy Manhattan street. I vaguely remember getting to my hotel room. In the middle of the night I felt sick and I vaguely remember vomit coming out of my mouth and spraying all over the room and the bathroom.

In the morning, the room was still spinning. I saw the clock and I was two hours late for a meeting. I went into the living room and the girl I had went out with the night before was lying on the couch with her legs on the floor and her clothes half off. I left her there. I got to my meeting, which was in progress but I was too sick to stay. I said I had a stomach flu and everyone let me leave.

I was gaining weight. I couldn’t sleep. I was getting depressed. Alcohol causes all of these things. It also loosens inhibitions. When I was single I wanted my inhibitions loosened. I vaguely remember drinking so I could get enough nerve to kiss someone. Finally I met someone who  didn’t drink. And she was healthy. So I married her. That’s how I stopped.



Efrain Martinez ‏@martefrain_: you said you hit rock bottom many times. Does it get easier? Do you stop worrying after a while?


The first time I hit rock bottom I couldn’t believe it. I assumed that I was going to go broke and become homeless. That my wife and kids were going to move in with her mother. That nobody would ever talk to me again. That everyone would laugh at me and my failures. I was almost right on every count. Probably everybody did laugh at me. I would go to the ATM machine and have a full-scale panic attack when I saw how much was left. I would lose money in the stock market and cry. I would look at my kids and cry. I was scared to fucking death. I’m sorry for the language. There’s no other way to describe it.

It became a self-fulfilling prophecy. The more I assumed the worst, the more I pictured it day after day in my mind, the faster it careened towards me.

If human warmth could be measured in temperatures, I hit absolute zero. I was cold and hungry and scared and frozen. Nothing was good. Everything was shit. Everything was less than zero. Everything caused my body to wilt, my heart to break, my stomach to hurt, my mouth to lie and then puke.

And it wasn’t the first time. I’ve hit rock bottom a few times. And that’s the good news.

Because the last time I hit rock bottom I didn’t think about it. Everytime I got scared about the future I just said to myself, “that’s the future. It will take care of itself. And now this second I just need to do the right things. Right now is not so bad.” I also knew that, statistically, the worst would not happen to me. It never fully did. So I knew that my mind was creating more worries for me than were actually there. Ghosts in the closet.

“The future will take care of itself”. I knew this was true. I didn’t even need to think about it. So I didn’t. I enjoyed the Right Now. And I’m glad I did. The only thing I forced myself to do was to stay as healthy as possible across all four bodies: physical, emotional, mental, spiritual. That’s where the mind tries to sneak in and trip you up.

And you know what, it worked. It was like magic. As long as I took care of the “right now” then the future took care of itself magically. Things would happen. Money would show up. The people around me would make the right decisions. Opportunities were thrown my way because I wasn’t running scared from them. Anytime I got scared I would literally hit my chest, stiffen my back, stand up straight and say, “I am abundant!” And it was true. I already was abundant, whether my bank account reflected it or not.

This is a truism: when you jump, you don’t need to look down. The net is there even if you can’t see it. And the net will catch you. So what do you look at? You can look at the sky. The blueness of it. The birds. You can take a deep breath. You can enjoy the ride. And when you finally hit the net and bounce you can say “wheeee!” all the way back up, because you know the net will always be there, and you’ll always have fun enjoying the ride as long as you realize we live in one big amusement park.

I’m afraid of many things. But rock bottom  isn’t one of them anymore. And as for the rest, who cares? I know that right now I’m having a lot of pleasure writing to you.



EdgeFoley ‏@EdgeFoley: I just found your blog. I appreciate the honesty. It seems like you struggle with your own advice, does it ever get easier?


Yesterday I was angry with Claudia about something stupid. And then I was upset with myself for not following my own advice. About what? About many things. About everything. We’re all human. Our bodies get sick. Our minds get sick. Our emotions get sick.

But inside, there is no sick.

If you are quiet and still. And just listen to your breath for just a second. And delay being anxious, delay thinking for just a second, just wait for it, then you can relax for a moment. Say, “I feel this anxiety and anger, but I’m going to wait a few seconds before I let it really bother me.” Keep delaying, even if you feel it in the body. I tried it. I still felt the anger but it was not the real me, it was sitting on top of me, pushing me down. But it wasn’t me.

In one way or other this happens to me every day.

The real practice is to acknowledge the feelings and thoughts that attack us all day long. These thoughts and fears happen all day long but we are parents and they are children. The key is to show your children where the boundaries are. Not ignore them.

When I feel overwhelmed with some emotion then sometimes it’s very hard to take a step back and say, “that’s just an emotion. it’s not the real me.” But I try hard to feel it in the body, where it’s hurting me: in my head, in my chest, in my stomach, wherever. And I just sit there with it. I don’t have to label it. Or be angry at myself for having it. It’s there. It’s painful. I can give it my attention. And wait.

Eventually I ended up right here. And the pain is gone.


Joshua Sheats ‏@JoshuaSheats: How does one to be an early riser? Nothing has ever worked for me.


There is only one trick to getting up early: going to sleep early. We all feel like we can’t go to sleep early. We might miss something. Often night is the time we can read. Or socialize. Or eat. Or drink. Or watch TV.

Well, stop all of those things. Don’t eat a meal after 5 or 6pm. Don’t watch TV (what’s good on TV anyway?). Don’t socialize too much (do your friends need to see you every night?). Don’t drink – its both a depressant and filled with sugar and calories, which will keep you up at night. Networking at night is ok, but you can’t do it every day. Maybe once a week.

The benefits of waking up early are enormous. You are able to focus better. Your day will be filled with success by the time everone is just waking up.

You can read more. You can exercise. You can think. You can work and nobody is up to bother you. You can meditate or pray. There’s no temptation to drink or eat a heavy meal.  You can see the emptiness of where you live when the sun just peeks out and lights it up. You can feel the freshness of the air. You can take a pad and after you are done reading, you can write down ideas.

You might not want to do this. It doesn’t work for everyone. But maybe try it. And see what happens. Try to starting “going down” around 7:30 or 8pm. And by 9pm you will be sleep, and by 5am you will have 8 hours of refreshing sleep. Try it. Will it kill you?


Grant Huhn ‏@granthuhn: Is the stock market “rigged”? I have heard floor traders called “Market Makers”. Also heard that everything involving $ is rigged


If you have to ask the question, then, yes, the market is rigged. And all the people who are rigging the market will tell you it isn’t. There’s a saying in poker, “if you can’t spot the fish at the table, then you’re the fish.” Guess what? In this very case, you are the fish.

The same thing is true with the market. You are asking about “floor traders called Market Makers”. That question alone means you are the fish. Do not put a dime of your money into the market if you want to save any of it. Unless you want to hold for the long run and pray for the best (ultimately the market is rigged to go higher in the long run but in the short run the market is rigged to take all of your money).

So, yes, Virginia, the market is rigged. The funny thing is: the people who think they are rigging the market are themselves subject to the people who are rigging it above them. There’s about 20 layers of rigging. The guys at the top are very happy if they avoid going to jail. They have done the rigging and made billions. Sometimes they retire and build great art collections. Other times they go to jail when someone in the government decides they’ve had enough of them.

Don’t be angry it’s rigged. It always has been. Every exchange in the planet has always been rigged. Our market is better than most. Don’t try to find happiness or sadness in the market because you’ll find neither. Even if everything around you is rigged doesn’t mean you can’t enjoy watching the sun rise in the morning.

[See also, “Who Really Makes Money on Wall Street?”]



arzvi ‏@arzvi: how to handle disappointing someone without burning the bridge?


One time I wanted to break up with a girlfriend but I was afraid to do it. I had no idea how to disappoint her. So I moved cities. And then four months later she finally broke up with me. And a few seconds after she broke up with me she called back and didn’t want to break up. And we went back and forth like that for awhile. Finally, she broke up with me for good. And she went and met a new guy. And got married, got a law degree, had some children, has a successful career and marriage. All because I was too afraid to disappoint her.

Don’t make such big assumptions. What was so great about me that I was so sure I was going to disappoint her. Her life is 1000 times better now without me. As is the case with just about everyone who has ever broken up with me or stopped doing business with me. What is so great about you that you are so sure you are going to disappoint someone. You have no idea. Nor do they.

Here’s what I do know:

– don’t make any big assumptions about who is disappointing who. That is just ego.

– don’t assume you will burn a bridge. Bridges that are burned are often rebuilt to be stronger and sturdier. Even if for awhile traffic has to go around a different path, eventually the bridge gets rebuilt with the newest materials. Trust in that. You can’t burn a real bridge forever. A girl who very tragically (to me) broke up with me 22 years ago (almost to the day) has recently gotten back in touch with me. Now we are friends and I can watch as her children grow and I can see how happy she is. That fills me with happiness, no matter how disappointed I was back in 1990.

– Be honest about how you feel. The feeling of “leave now” will eat at you until you do it. Be honest, be straightforward, and you will avoid much pain that will happen anyway. You are already on an inescapable path to doing what you have to do. So just do it now and be honest about it.

– You’re not so great. We’re all trying to figure our way out in the world. We all need some adventure until that right situation comes along where we can settle down and relax. Sooner or later you have to get on with it. And so does the other person. Don’t hold out. Just do what you have to do and make everyone’s life better.



Efrain Martinez ‏@martefrain_: when you quit your job and focused on your business, did you still hate mondays?


I used to love my job. It was only when I began to hate Mondays, in fact when I hated every day, that I knew I had to quit it and focus on building the business that until then had just been a side-business.

I built the business up and eventually sold it. It was a good result.

BUT, here’s the problem. You never get rid of the Mondays. Every day becomes a Monday. When you are at a boring corporate job you have several things going for you: nobody really cares that much at the job. Everyone leaves their work at the desk. Everyone takes off weekends. Everyone takes vacations. And during the summer nobody is expecting much from you.

That all changes when you have your own business. Here are the things you suddenly start worrying about:

– is every project getting done on time

– what else can I be doing for each client

– how do I get new clients. It’s hard. Do I just cold-call them? How do I get word of mouth going? Do I go to parties? Do I “pivot”? Argh, what do I do!?

– I know I have enough cash coming in to pay employees for 3 more months. But what happens then? What happens on month 4?

– Will my family survive if the business crashes in 12 months?

– Who can I sell my business to? How do I start preparing to sell my business?

– One of my employees today is crying because her boss (my partner) was talking about her behind her back and she heard? How do I talk to her about it? How do I talk to him about it?

– Another employee is sleeping with another employee and its not going to work out. How will this effect the project they are both working on for our biggest client?

– I feel like I need a head of sales but everyone I talk to wants a big piece of the company? How do I structure this?

– Should I productize my service? Will I make more money that way?

– How do I get client XYZ to pay his bills?

And on and on. The worries never end. You never sleep. Every day becomes Monday. Every minute becomes 3am Monday morning. Every day there is constant battles and meager successes to drive you forward. And sometimes there are stretches where it’s all 2 steps forward and three steps backwards.

I never once considered going back to the corporate job. It would be embarassing. A failure. I had to keep going forward. But the Mondays never ended. And 17 years later, the Mondays still don’t end. But you get used to it. Heck, it’s Monday right now! And I have 10,000 times more issues than I ever had at a corporate job . But over time the problems that used to be hard get easier. And the problems that you have today become opportunities. And the opportunities get better and better because you learn which ones smell, taste, look, feel better. And it’s no longer two steps forward three steps back. It’s five steps zig-zagged. And one of these days I’ll reach the end of the maze and a unicorn will be there. And I’ll ride her away and never look back.


Andrew Ferri ‏@Andrew_Ferri: you’ve chronicled your experiences as a father, what is your top-ten list when expecting?


I was scared to death when my first wife was pregnant with my first kid. I wasn’t ready but maybe nobody is. I didn’t want to have kids initially although now I’m certainly glad that she’s a healthy 13 years old. Shit, I can’t believe it’s been 13 years.

One time, while my ex was pregnant, she asked me to take out the garbage. I grabbed the green bag and threw it down the incinerator then I did what I did every single night during the entire period of her pregnancy. I went out and played poker all night at the Mayfair Club on 25th Street and Madison. It was only later I realized what I had done: I had thrown out the bag of all her post-pregnancy clothes. The specific clothes that would fit her when her body was in between “here” and “there”” after having the baby.

Of course I didn’t tell her.

So it was only, post-baby, when she was getting ready for an Easter party, that she realized she had no clothes. Zero. I had thrown them all out six months earlier. She was upset. Very upset. Crying upset. I grabbed my baby and I didn’t know what I was going to do. I felt like holding onto the baby would be the only way to protect myself. The baby was crying. I felt like if we both jumped out the window 21 floors up, then this problem would be solved.

I didn’t do that. I didn’t do a lot of things. I would go out for a haircut and not come back for five hours. I’d sit in the coffee shop across the street and read. Ahh, peace and quiet. I’d call and say “there’s a big line to get a haircut”.

The whole relationship with my ex-wife changed when we started having kids. I started to travel more. I kept playing poker. I went on a self-sabotage binge that cost me all of my money, cost me the house we bought and rebuilt, cost me many hours and months and years I could’ve spent with my child. I’m thinking about her right now, all of 13, in her teenage new-hormone daze. How many months did I waste not getting to know her better? Is it too late for me to make that up? I hope not.

I remember one time I went to drop her off when she was 18 months old at some sort of kid-play-music thing. As I was walking out I heard her say in the tiniest, squeakiest voice, “bye daddy.” And it stopped me. She was waving. My eyes teared up.

And now I wonder. Will she ever miss me that way again. Will she ever need me that way again. My eyes are tearing up.

Maybe some other time I’ll have a top ten list.



emmanuel olaoye ‏@Mandizzleno1: Thanks James. This one is for me. what are your top 3 tips for narrative writing.


I wrote a post “33 Unusual Tips To Being a Better Writer” and I’m really afraid I won’t be able to compress it down to three but I’ll try.

A) Forget the intro. Everyone obsesses on how to start something. So let’s make it easy. Don’t start it. Just forget all about an intro. Intros are always boring and bad anyway. Which leads to…

B) Start in the middle. Let’s say you are telling the story of how you lost your virginity. Don’t start with how you met the girl (or guy). Start with how bad it was. And how bad you felt afterwards. And how anxious you were that she would never call again. (uhh, maybe I’m projecting too much of my own story here). How you met her is sort of boring.

C) Ok, back to the actual first sentence, now that you’ve given us the middle. Start with a cliffhanger. The very first line. Like in my answer here. I wrote down the three items first (including this line). And now I’m going to go and write that first sentence.


Robbie Laney ‏@robbielaney: Do you believe in God? If so, which?


Unfortunately the word “God” has been bastardized. It started off as one thing and then it’s gone through the religion grinder, the New Age grinder, the self-help grinder, the atheist grinder, the science grinder, and what’s come out is a cartoon character of an old man with infinite power who gets angry sometimes.

But yes. I believe that I am God. And so are you. The universe loves to create. Ever since the Big Bang all the Universe has done is create. It created a bang, it created dust, and stars, and galaxies and planets and life forms and brains. All of these atoms stuck together in trillions of miraculous ways that created consciousness. It created you and me.

We are experiments. The universe wants to try something. So it sliced a piece off of itself and made you. It made me. Eventually we go back. And it/we keep making things. Forever.

It’s one big toy. And each toy is brought to life via the breath of god. Including you and me. The breath brings us to life. The exhale brings us back Home. Where we will all go? How do I know? I don’t. But try for just a second to say, “whose body is this?” Then, “whose thoughts are these?” Then, “who is the one asking this question?” And go down that rabbit hole as deep as you can. Do that every day. Somewhere in there, infinitely deep into that rabbit hole, is that initial breath that created everything, that is the only thing inside of everything that exists, including you and me, just different reflections in the same mirror.

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