IMG_0007When I walked out of my job for the last time I wondered if I’d have a cinematic moment that encapsulated all the emotion of the situation in one suspenseful scene. That would make an easy blog post.

As I write some 3 months hence such scenes have been so numerous it’s hard to know which to choose.

Today I checked my Paypal balance and discovered it’s lower-than-expected. And it’s the first of the month. I’m expecting a mid-four-figure payment from a new client, but not until the 18th.

I check my email. Great. A client I emailed yesterday is finally sending the last payment of a performance-based contract. But it turns out he’s probably not renewing.

I dash off a quick follow up: “Has anything changed since May, when you said you were interested in ongoing service?”

Ten minutes later, the vulnerability hits. “Shit. Did I push too hard? Am I going to get a ‘BRO – let it GO already’ response?”

But I’m getting the money.

So that’s the gist.

Quitting your job to be a full time entrepreneur/consultant is like becoming a professional gambler and a porn star all-at-once. It’s quitting your medication. It’s having kids.

And that’s not hyperbole. There are two extremely specific emotional components. The first is the introduction of multiple dopamine loops into every day. Like when you’re hoping for that promotion, and it happens. Or it doesn’t, then you learn your buddy got one. In your day job, loops like this happened once-a-season.

As an entrepreneur/consultant, they happen multiple times-a-day.

That’s the pro-gambler angle. The slot machines.

The second effect is that of feeling naked or, more accurately, waking up and knowing you did some crazy sexual shit the night before, but not being able to remember exactly what.

That’s because of all the risking rejection. And that’s what selling is. Risking rejection, in a small way, every time. Every sales call. Every follow-up email. Every time you ask a mentor for a hookup.

Veterans call it “moving toward resistance”, borrowing the term “resistance” from War of Art author Stephen Pressfield. Resistance is the peculiar species of excuse-making that seems to arise whenever something scary is the shortest path to a goal. “Moving toward” it means doing that scary thing.

I had that feeling precisely three times at my day job: asking for a promotion, asking for a raise, and quitting. Now, it’s a daily occurrence.

Why is overcoming “resistance” scary? Because it can backfire.

If there were zero risk of being told-off after asking for a guest-post (a common strategy to get website traffic for a fledgling business), everybody would do it.

If needing to justify your value under heated questioning wasn’t harrowing, consultants wouldn’t make more money than freelancers.

One thing I expected to worry about, but haven’t, however, is money.

I worried more about money when I was employed. The stressful thing about money isn’t needing it – it’s not being able to produce it.

That’s not to say it will never be a concern, but what runs through my head when I wake up at 3am isn’t “how am I going to pay my bills.” It’s “did I push too hard on this sales call”, or “did I come across as too aggressive to a mentor when I asked for a guest post”.

Paying the bills when you’re a consultant/entrepreneur is like knowing you need to bring home the big game, but you know how to hunt, and you have a pretty good idea where the really choice game is, and, barring that, you know where to find the odd rabbit or muskrat you have an 85% chance of bagging.

As an employee, it’s more like expecting somebody to deliver the kill to your front door, but you’re not allowed to own a spear. And the kill is the same size every day, unless you convince them to bring you more. And one day it could just stop.

There’s one more angle: hunting is a lot fucking more fun than waiting for a carcass.

Of course I don’t expect to be out hunting for the rest of my life, nor even any longer than I need to. Consulting is always a means-to-an-end of starting another automated business. 80/20 Drummer reached its point-of-diminishing-returns just as people were starting to hit me up for help with their sales funnels, so cutting 80/20 Drummer loose to earn under its own power (another thing lessening my anxiety about money) while I started consulting as a marketer made sense. My broad-strokes goal is to do for marketing what I did for drumming.

And just as a drum teacher starts with students, I’m starting with consulting clients. Get cash-flow and market intelligence, all as you build your list.

I’m also interested in the meta-skill of starting businesses. If growing 80/20 Drummer to a decent size was finding one lucky fishing hole, starting a new business is learning how to find fishing holes, and what bait to use. It’s that “never go hungry again” shit.

As I write this, another payment lands in the Paypal. And I’m talking to my travel agent about my trip to Asia in late September. But the flight I thought I was going to take wasn’t available anymore.

So it’s ups-and-downs. But it’s really difficult to complain.


I actually love New Years resolutions.

But I think the most fun part is looking at resolutions for years past. It keeps me honest. Counterintuitively, I often discover I was aiming too low. Here are my resolutions from two years ago:

1) Stop mentally over-committing at my job.

2) Figure out, hypothetically, how I could be bi-coastal starting tomorrow if I needed to.

3) More mundane: break tasks into whole days. E.g. Monday, Tuesday, Thursday I’m only required to do stuff for my job. Wednesday and Friday, I’m only required to do things for my business.

4) Increase my earning power so as to pass the “minimum happiness threshold” – where money is not a concern – beyond which more money has diminishing effects on happiness.

5) Get seriously better at Mandarin. I don’t want to go through another Taiwan trip where I’m speaking pidgin. I don’t have to master it, but the next trip I want to see some serious improvement in my vocab and ability to read. It will make me feel better.

Several seem comically easy in retrospect: Stop over-committing at my job? Figure out how I could be bi-coastal? Break tasks into whole days? Those all read like journal entries for Monday morning. Things I could wrap up in 10 minutes. Gee – open the calendar and block out some stuff? Think I probably need a whole year for that. Open Airbnb and see how much I could rent my place in New York for and what the going rates are in LA and San Francisco? I might need till November.

Only 4 was a reasonable “push goal”, and it did indeed take me about a year to accomplish.

5? Let’s not talk about 5.

So what can I learn about setting goals from the way these turned out?

Well, at the risk of restating a cliche, Think Big. Since I made the 2014 list I’ve read Gary Keller’s The One Thing, which is sort of the modern bible for goal setting. But I construe it this way: if you’re undertaking a life/mindset journey, you’ll be wary of over-committing at the beginning, for rational reasons: everybody and their mom sets audacious New Years goals, and gyms are mostly empty by February 1. And you’ve probably let yourself down on a resolution-or-two.

So it makes sense to start small. Earn your own trust. Give yourself an early win.

Just a digression – there are so many different “gurus” offering seemingly different advice about this. Tim Ferriss touts the power of “unrealistic goals”: his classic example is you wouldn’t get out of bed for a free trip to Cleveland, but you might change some habits for a trip to the Greek Islands. This is true, like most adages, depending on the context.

How can “set realistic goals” and “set unrealistic goals” both be true? The same way “tighten the suspension on the right side” and “loosen the suspension on the right side” can both be true in a pit crew. (Can you tell I haven’t been following NASCAR very closely this year?) The direction you’re headed depends on where you start.

Anyway, start with realistic goals, because you want to make it easy to accomplish them. Not “finally lose those 50 pounds this year”. Instead, “go to the gym six times in January”. Treat yourself like a kid, until you’ve proven you can be trusted more like an adult, then treat yourself like an adult.

But back to the original takeaway: Think Big. At every stage, you’re recalibrating. That’s why reviewing past goals is important. You may discover, as I did, that you should have aimed higher.

That’s why I’ve found it’s been useful to be Slightly unrealistic. (Which differs from “lose those 50 pounds” in that’s grounded in a firm understanding of what’s “realistic”.) Think of it this way: when you accomplish a goal that requires a mindset shift, by definition, the world will look slightly different to you at the end of the process than at the beginning. My two favorite examples, both paraphrased from my memory:

“If I’d asked people what they wanted, they’d have told me they wanted a better horse-drawn carriage.”
-Henry Ford

“People don’t know what they want until you create it for them.”
-Steve Jobs

Old You is beginning the goal, and New You is completing it. But if you asked Old You from a year ago what was realistic, you’d probably find his answer narrower in scope than the answer Current You would give. That’s why you have to compensate for Old You’s provincialism by setting the bar slightly high.

Which brings us to resolution #1:

1) Make 15k per month by next year.

I just revised that up, then revised it down. Originally, I chose 8k, figuring that that would cover Chih-Yu’s escape from Juilliard. But then I realized if I’d asked Nate of one year ago what was realistic, he’d never have named the figure I’m currently making. (He wanted that amount, but he wouldn’t have allowed himself to believe it was realistic.)

Then I chose 20k. I revised it down because Current Nate doesn’t believe it sincerely enough to go after it. Deep down I’d assume it was so high as to be arbitrary, and it wouldn’t have the effect of pushing me to grow. I’d probably be running this script: “there’s no way I’ll hit that 20k, so I might as well just ‘do my best.'”

15k is scary.

It’s hard to conceive how I’d hit that. It would require rethinking some things. But after attending the BKK conference in October and seeing people just like me (but a little more experienced, and a little less in-their-own-way) blowing that figure away, I can’t say it’s unrealistic. It might push me to start a new business, or at the very least imagine the 15k/month incarnation of the Current business, which is scary. It forces me to confront questions like “what would I rather do: stay where it’s safe and require Chih-Yu to stay at her day job for another year?”

A quick digression about money goals:


Nate of 3 years ago would have found this obscene. “When is enough enough? What’s with these one-percenters always going after more money? Aren’t there other things in life more important than money? Why not make a goal to give away 15k instead of earn it? Or help 2 people a month?”

Ooh – that last one seems like a great goal, actually. And maybe the second-to-last for some years down the road. But as to the first 2, 3 Years Ago Nate had yet to make several mindset shifts:

  • Earning money is not zero-sum in the internet age. Anyone lucky enough to have the opportunities and education I’ve had could go out and do the same thing. It’s not for everybody, but not to do it is a choice.
  • Nobody owes you a living. If you’re lucky enough to be a winner of what Warren Buffet calls The DNA Lottery (born in the USA or another advanced economy in the First World, with a decent upbringing and education) and you still choose to accept only those opportunities given to you, you’re putting yourself at the mercy of somebody else’ whim to hire you/fire you/give you a promotion/pass you over for a promotion or raise/force you to work 80 hours/make you lick the corporate boot/etc. If, by contrast, you choose to go into business, you’re no longer getting a “guaranteed” paycheck or employer-provided health care. You’ve got a family, you’ve got parents, and now it’s on You, B. Given that the ceiling’s off your earning potential and you’re not taking anything from anybody else by earning a living, how much do You need to feel comfortable?

But it’s Not all about money. Steve Jobs, Elon Musk, Peter Thiel, Kevin Kelly, Derek Sivers… All of these guys have said it was never about the money for them. My assumption is there’s still some Old Nate mindset garbage holding me back. Here’s one script I uncovered that’s almost surely wrong:

  • It’s dog-eat-dog out there. If you get some paper, hang on for dear life.

I know that’s wrong, but I still hold onto it.

How crazy is that? It just goes to illustrate the difference between nominal and real mindset changes. You can say anything you want, but what do you believe? Anyway, it’s like the kid who’s intimidated by the bully. I’ve taken the somewhat controversial position that if you’re scared of the schoolyard bully (and in an ideal world where there are no concealed knives or guns) you should fight him. Why? In small part to make yourself a “hard target” and “not worth the trouble”, but mostly to prove to yourself that you’ve got it in you.

If you’re Holly Holm or Conor McGregor, however, with nothing to prove, maybe buy that bully a drink. The analogy? Jobs, were he still alive, Musk, Thiel, Kelly, and Sivers could lose their shirts tomorrow, and they wouldn’t go hungry. Why? They’ve got skills, networks, and the ability to live with fewer material things. But I’m still proving to myself abundance exists. I’ve still gotta fight that bully.


Still, set goals your Future Self would think are realistic. So, #2:

2) Help 2 people per month for no reward save the positive feeling of helping someone.

I think Future Nate knows that’s a big component to “success” anyway. How might I do it? Help people escape their jobs and get into business? Help musicians get some real mailing lists up? Volunteer? We’ll see.

One thing I did last year that wasn’t a moneymaker at all was nonetheless one of the most meaningful things I did, and it not only (hopefully) helped others, but forced me to grow.

3) Give at least 6 drum clinics in separate locations outside New York.

I can knock out 3 in one fell swoop in Asia, and I’m already doing one in LA this month. This goal will motivate me to find 2 more opportunities. Some people derive all their meaning from starting businesses. Others find some meaning in business and some meaning elsewhere, and I’m in this latter category, especially since one of my goals for 2015 was to automate my business to the point where my only job is to grow it. How do you avoid spending all your time on social media? Have things that give you meaning. Music is that thing for me, and the clinics are the best motivator to get better I’ve yet found.

Finally, #4:

4) Spend at least two months outside New York in 2016.

Future Nate will likely feel this is thinking small, but it requires Chih-Yu to be able to quit her job first. Location freedom is important, but I realize it’s another Bully Goal – something I have to prove to myself I can do, then I may not “need” it so much.

I have two young entrepreneur friends who LOVE New York. The shops on 5th Ave. The salarymen trooping though the rain to get home at 8pm. My relationship with New York is more guarded. My suspicion is that’s because my friends have never worked day jobs here. They’re Holly or Connor. They have nothing to prove. They’re 100% sure the joke’s not on them.

I want to have that kind of relationship with New York, and it starts by being here because I want to be, and not because I have to.

Anyway, thanks for sticking with me through a long one. Who else has New Years goals? Leave a comment below this blog article, or, if you’re reading this on Facebook, below the post. Let’s revisit them next year and see how we did!


My entire life, until October 27, 2015, was structured around the premise that the majority of each weekday needs to be occupied either with a job, or with escaping that job. In New York, that’s how I’d filled my days. The moment I stepped off the plane from Hong Kong, back from my 3-week trip to Asia that included in-laws, drum clinics in 3 countries, and a business conference with the only organization I’ve every been proud to belong to, I knew everything had changed. At the risk of sounding hacky, I couldn’t go back.

This Wednesday will mark the two-week anniversary of my giving notice at my job, and I’m only now circling back to write the post I’d visualized writing since last March.

It happened exactly the way I’d fantasized about it. But I’ll leave the sordid details out. You’re probably more interested in the how and the why anyway.


I returned from Asia with 3 things highly destructive to holding down a job: an appetite for slow international travel, a business knocking-on-the-door of being able to support me, and a vague sense that everything would be alright. That sense wasn’t just superstition. I’d finally spent enough time around people making money without employers to know (a) that it’s possible, (b) a lot of the particular shapes that possibility tends to take when it turns into success, and (c) an assurance that even if my primary business isn’t the be-all-end-all, I already have skills people will pay for, because (b again) I’ve seen them paying for it.

Other members of my entrepreneur network greeted the news that I’d quit with knowing smiles, the way a coach meets your eyes the first time you pull off a muscle-up. “I knew you could do it, and I was hoping you wouldn’t wait too much longer.”

But why not just stay in the job if I’d already pulled off the hat-trick from 4HWW? In short: being able to sleep at night, and breaking out of somebody else’s frame.

Too abstract? Imagine taking money from overly meddlesome parents. It’s about like that*.

The first bitter pill is knowing you’re not “living up” to expectations. As long as you’re taking a salary, it’s presumably for providing something in return. In my world, it was for being a “good employee”. For the last three years I’ve been a mediocre-at-best employee, especially by the metrics my company keeps, and I didn’t like that incongruence. Sure – I can justify my actions by telling myself I was still proving value to the company in excess of my salary (True, by my belief), and further that I was in a system that incentivized otherwise good people to do ethically dubious things (as Sam Harris speaks about in Lying), but it’s still core to my beliefs that both parties in a negotiation should feel they’re getting what they need from the deal, and I’m not sure I can say that about my employment relationship.

The second is feeling “in orbit” around a planet you don’t want to visit. Money is gravity, and even if you’re not physically in the office every day, every day spent yoked to the destiny of people you don’t want to be in business with is a spiritual drain.

So it was with a giddy sense of relief that I walked out of my office.


If I’m not taking a paycheck, what am I doing? Well, I’m hopefully growing my business to meet the need by the time the Deadline comes. I’ve weighed my options a million times, and run the whole situation by some very smart people, but in the end it came down to my gut. As Gary Vaynerchuk says, “you should leave when you’re suffocating.” If I was nervous about the outcome before the meeting, afterward I realized I couldn’t have taken another day. If I were writing the movie of my life and I could choose the most optimal day, armed with all I know about the viability of my business(es) and the bandwidth-opportunity-costs of being employed, it’s hard to picture a better day than two weeks ago this Wednesday.

My business has grown, mostly through trial-and-error. There are only three ways to make more money. More customers seeing your offer, more of the customers who see your offer buying, and each customer spending more. All the mumbo-jumbo on the podcasts boils down to that. I’ve been pulling firmly on each of these levers for months. Sometimes an intervention will make things worse. Other times, it will make things better. Know the difference between the effects of your interventions and random chance, then do more of what’s working. I’ve done just enough to see the trend lines headed the right way. The only other question is market size: if I capture all the demand in my market, will I “top out” and reach a glass ceiling. I’m reasonably certain that’s not going to be an issue.

Please don’t mistake the acceptance-of-my-fate in this post for arrogance. I fully expect to sweat between now and the “deadline”. To pound the table. Realities like health insurance have already intervened. $600/month for a decent plan. Picture shouldering that, and feel the knot in your stomach. Picture that lump sum you’re used to seeing in your bank account every first-of-the-month not there anymore. Run your eyes down the imaginary spreadsheet of your monthly expenses. Then think about everything you hoped to do this year. Travel, ….hmmm – mostly travel;) Then think about emergencies.

“What’s the worst that could happen, and what could I do then?”

Well, I could probably stay on with the company if I agreed to the rules a little better. I could take an apprenticeship. Slightly up the totem pole, I’ll continue to float consultancy proposals. This is assuming the worst-case-scenario: my business doesn’t grow a bit. Even in that case, there’s still ample opportunity to pay off my debts and save a little before the “deadline”, which will reduce my monthly expenses.

But I prefer to spend my mental energy focussed on how to improve the Right side of the ledger. (As a friend recently said “if your dream isn’t coming true it’s probably because you’re too focussed on its absence and not focussed enough on its presence”. ) And I’ll write a tactics post (similar to several I’ve already posted in my entrepreneur group) soon.

The meta-point is that, as far as I can tell, existing in this space of risk-mitigated uncertainty seems to be what Freedom, and maybe Adulthood, tastes like.

* I should mention I’ve zero real-life experience with meddlesome parents as both my parents and my in-laws are astonishingly supportive.

Belated New Year’s Post 2 – 2015 Edition

“I guess I’d take a thousand a month.”

My companion stared at his drink, unimpressed.

“You’re going to quit your job on a thousand?”

I reconsidered.

“Five thousand?”

“Your wife’s going to quit her job on 5,000?”

“Okay, okay. Ten thousand.”

And so went the happy-hour-cum-lifecoach-session with my friend from my entrepreneur cult, a “made” guy we’ll call Pete (because that’s his real name), who, as I understand it, is now hanging out for three months in Bali just because he can.

There are multiple reasons it’s finally appropriate for another post, even though I can feel Breaking Ferriss using up my “glucose”. Well so-much-the-better. I’m not writing sales emails today anyway. The rest of my hard-won creative energy, I plan to donate, at pennies-on-the-dollar, to my day job. But I’ll get there.

It’s early in the year in 2015, and I just finished a product launch, so it’s worthwhile to talk about those things. Probably more worthwhile now than after I discover whether the launch has been a “success” or “failure”. I’ve also been getting into the extremely life-hacker-cult habit of “morning rituals”, which everybody from Ray Dalio and Peter Thiel to the Brain Pickings lady says they do. (There’s a small chance it’s because they’re all getting coached by the same charlatanic life-coach – an idea that gives me a smile.) The morning ritual that’s all the rage now, and which I suspect will soon occupy the dustbin-of-bygone-fads along with Hare Krishna, Primal Scream Therapy, and AIDS, is meditate-then-journal. Long-story-short, I’ve been meditating, which has been going pretty well (dig that erudite description, haters), and the “journal” component, which may have originated as a way for people to sell journals (I’m not kidding), I’m directing into Breaking Ferriss. “Don’t waste glucose describing your personal journey, but journal every morning.”

Loophole, methinks…

So it’s 2015, and how did I do on those resolutions from last year?

1) Give less mental import to my day job (location of which I’m no longer going to mention by name in this blog because it turns out there’s a thing called “linkedIn”, and potential employers actually search the internet for you). (Strange, the choice society hands you – between truly being yourself and realizing a resonant level of creative honesty and being employed at a “reputable” company. As if between me and Joe Rogan and David Choe there’s a chasm of unemployability. It makes sense, actually – there’s that Seth Godin “dip” again. If it was easy, everybody would do it. Anyway, it’s now slightly more difficult for the lazy – read “average” – HR person to find anything on me other than a sterling work history and no tattoos.)

2) Spec out what would be necessary to be bi-coastal. Could I do it with no more money than I had at this point last year, with no change of job, etc.

3) Break tasks into whole days, with no more than one mission-critical task per-day.

4) Increase my earning power into the “minimum happiness” threshold, so as to remove money as a stressor.

5) (Which I actually labeled as “4”, resulting 2 “4s”, then decided to leave that way because I liked it.) Get better at Mandarin.

So how did I do?

Well, the mental-energy-at-work thing is a tough nut to crack. My assumption had been that I could negotiate a part-time/remote arrangement with the boss, then fulfill my obligations in stellar form, and everybody would be happy. Two things went wrong with that. First, I’m part of a team, the other members of which have within their reach the ability to negotiate any arrangement they want, but chose do nothing, and continue to sit at their desks from 9-6 Monday-through-Friday. Good on them. The issue? Instead of changing their lives, they began to resent me for the arrangement I’d negotiated. They’re good people and this isn’t a dirty-laundry session. The takeaway was really “teams don’t work well unless there’s a shared ethos”. I think a Four Hour Work Week-style remote work arrangement could work in cases in which I was a cog in a big wheel, judged by monthly results, or part of a team that shared a culture of efficiency and effectiveness. As it stands, it’s a constant game of cat-and-mouse to avoid getting “meeting’d”, and I’ve given into some concessions, like “face time” at the office to reinforce that, even though I don’t punch a clock like the others, I still have their backs.

The other things a successful remote work arrangement requires are fixed and clear systems and performance metrics. “Is Joe handling the remote thing well? You Bet he is – just look at his numbers from last quarter.” There are no such metrics or standard operating procedures at my job. Everything is re-invented each week at the Monday Meeting, which can result in a frustrating degree of “project creep”, in which nobody remembers what we agreed to do last month, but that’s what I’ve been trying to measure up-to, only to discover we’re now doing something totally different. As such, “performance”, to the degree it’s “measured” at all, is measured by hours in the office.

Blah blah so how am I coping? I’m doing my best to deliver the 80/20 of what they need, and drawing boundaries – insisting that people adhere to the agreement I made last August – while walking the tight-rope of trying to keep people on the “team” happy. That’s what they don’t tell you about in FHWW – the interim between starting your business and leaving your company, if your company isn’t system-driven and performance-based.

I’ll skip to something positive. Number 3 – achieve a minimum-happiness income. With the earnings from my business increasing steadily (if slowly) that now seems within reach. Indeed, if my day job was a cake-walk, I’d be tempted to add up the job income and the business income and call this experiment a success. As the conversation I described in the opening to this post alludes, the positive side of the day-job-doldrums is it’s forcing me to think bigger.

The question for 2015 is: What if I had to quit my job by May?

What could I do? Would the business be able to ramp up enough by then? It would need to grow at a pretty staggering pace. What other options do I have? Transitional jobs? Part-time jobs? The bottom line is I need to average slightly more than I’m currently making at my job before I’ll feel comfortable making the jump. But this experiment in thinking big is putting me in the headspace I need to be in.

Last fall I solved two crucial problems with my business. Finding something people were willing to pay me what I wanted to charge for it, and removing selling my time for money as a bottleneck to scale. I had been doing one-on-one coaching, which people in my niche are just not willing and able to pay me enough to make worth-my-time. Luckily, there were more-than-happy to pay for a biz-training-style online course with multiple modules, so I took a version of the curriculum I’d been using for coaching clients and put it up on a membership-site platform on WordPress. The course has been selling at an agreeable conversion rate, and my customer acquisition costs are next-to-nothing, thanks to a simple hack I’ll talk about in a future post. The only problem left to solve is scale, and that takes time. But for the first time, I can report that I have a viable, scalable business model.

Which also resolved a big quandary from earlier in the year: should I be doing the business I’m doing? When Dan Andrews and Dan Norris are out there preaching “get up-and-running-in-seven-days”, what am I doing wasting months teaching drummers? The answer is a simple one, and the same problem I solved with my existing business – Product-Market Fit. “Can you find something your clients value enough to pay you an amount that makes it worth it for you to supply it to them?” Most “success stories” with the “seven day startups” have programming or web design experience. “You can start a consulting business by selling your WordPress problem solving expertise.”

Yea. No shit, Sherlock. I can also breathe through my nose by closing my mouth.

But the starting point of these entrepreneurs is Second Base – they already have a skill other entrepreneurs are willing to pay top-dollar for. For those of us starting from scratch, doing B2C (business-to-consumer) stuff, we need to build those skills. Which takes us to another extremely common tactic – so common it’s a little odious. The Parlay. Example: I had to learn a platform called Member Mouse (and will likely learn one called WP Courseware before this thing is concluded) to host my course. Once my existing business reaches its apogee, its success becomes the primary selling point for the membership site consulting, which I can sell at a far higher price than drum lessons, and that’s the parlay. My dream is still to be the Pat Flynn of the drums, but forced with a choice between freedom and more-of-the-same at the day job, I’ll hang a shingle as “the membership site guy” so fast it’ll make your head spin, Private.

Ok – at the 1500 word mark I think that’s enough for one post. Back soon with more details.

Happy New Year, all.

Ari shaffir, the Comedy Store, and the Perils of Being Picked

A recent episode of Ari Shaffir’s excellent podcast got me thinking: when is it okay to Be Picked? Ari spent four years trying to impress the owner of the comedy store, Mitzi Shore, before she finally made him a “paid regular.”

Being Picked worked for Ari. His efforts to outgrow, outwit, and outlast his obstacles paid off.

Context: the Comedy Store in LA launched the careers of robin Williams, Richard Pryor, Andrew Dice Clay, Damon wayans, and Jim Carey, and Ari Shaffir (now a successful touring comic with specials on Comedy Central) got a job manning the phones there in 1999. Mitzi Shore viewed the Store as a talent factory. If there was no possibility you’d succeed as a standup comic, she didn’t want you there, even to collect tickets at the door. (She routinely fired people from non-performance jobs after they bombed at open-mics.) She organized the store into a hierarchy. At the bottom were employees, who could perform at open mics. One level up were “unpaid regulars”, who had more performance opportunities, but as the name implies were not paid to perform, and at the top were “paid regulars”, who were.

In the podcast episode I link to, Ari describes “showcasing” for four years before getting “passed” to be a Paid Regular. (Showcases were Mitzi’s auditions.) You’d have to listen to the episode to understand the depth of Ari’s anguish over Mitzi’s continued refusal to “pass” him, as 34, 35, then 36 showcases came and went. “You were great. You’re an upaid regular!”

“I’m already an unpaid regular.”

“Well you’ll be comfortable there then, since you’re used to it.”

Was Mitzi torturing Ari? Why? Other comics began to advise Ari to perform outside the Comedy store, in order to get deeper and broader experience. Four years after he began, after performing almost 40 showcases and watching many of his friends “get passed” before he did, Ari was finally made a Paid Regular, an event he still describes as the greatest accomplishment of his life.

The ordeal prompted Ari to consider the true meaning of “faith”. Real faith, he decided, is when you continue to believe something despite zero evidence. Any rational person in his position should have given up, he says.

But I submit that Ari’s perseverance was not an act of blind faith, but rather a response to well-honed instincts, and that to attempt to transplant his story onto other experiences without a much greater understanding of context is risky. It’s tempting to view Ari’s story as an affirmation that if we persist long enough, we too will Be Picked.

There’s another side to this, though. Consider the story of Duke Fightmaster, hero of a 2010 This American Life epidose called Last Man Standing. Fightmaster decided he wanted to replace Conan O’Brien when Conan left late night to take over the Tonight Show. The shortest path, he decided, was to launch his own talk show, complete with brick-and-mortar set, camera-people, and guests. The show got some recognition on local news and had a small “bloomlet” of popularity, but as the months wore on, its audience dwindled, and people helping out with the production started to move on. I’ll have to re-listen to the episode, but I remember that Fightmaster persisted even after Jimmy Fallon took over Conan’s spot on Late Night.

So everyone wants to be Ari Shaffir, and nobody, I’d wager, wants to be Duke Fightmaster, still “fighting” when it’s clearly wasted effort, while friends and family whisper “do you want to be the one to tell him?” But how do you tell whether you’re Ari (whose family, by the way, told him the same thing Duke’s told Duke), or Duke?

Now we’re asking the right question.

I’ve covered The Dip and the Persist-or-Cut-Bait conundrum on this blog before, in the context of whether an entrepreneurial venture is worth sticking with. But Ari’s story illuminates a slightly different facet – when should you persist in trying Be Picked, and when is it time to move on? It’s especially prescient for me, because jazz has a Comedy Store too (musician readers will know what/whom I’m talking about – there’s no need to go into further detail) and I’ve long-since made the decision not to spend any effort trying to Be Picked by them. So I have some need to believe that my situation was different than Ari’s – that quitting was the wise move for me. But I’ll still try to call it straight.

I would submit that success or failure being Picked is not a pure roll-of-the-dice. I think we can look at Ari’s story and find some evidence that he was going to succeed – that his faith was not misplaced. Moreover, he was doing some key things right that we can learn from:

1. He was working on his craft in a non-“burndown” situation. Entrepreneurs would say he had a “long runway.” All-the-while Ari was continuing to go up in front of Mitzi and test the waters, he was continuing to perform and get better. He was also living sustainably, at least financially – working two jobs and keeping his living expenses low. He wasn’t burning through savings and/or other people’s favors/patience. There’s a takeaway – can you become/are you becomming better at this thing you’re hoping to be Picked at? Have you structured your life so you can afford to put in tremendous time to build up the craft and relationships necessary to succeed?

2. He had a direct relationship with the person in the position to Pick him, and there was evidence that being Picked by Mitzi Shore (a) was possible, and (b) would portend a degree of success beyond the Comedy Store. The fact that Ari’s friends were getting “passed” was not reason to Fret – on the contrary, it meant that Mitzi would pass people when she felt they were ready. Mitzi could have fired Ari (and threatened to on numerous occasions), but she didn’t. She made him an Unpaid Regular, and continued to give him encouragement. It’s impossible to know what she was thinking, but it’s possible she felt a greater responsibility for Ari’s success than that of some of his colleagues, because she knew being passed was so important to him.

There was a time in my life when I believed being Passed at the Comedy Store of Jazz would mean I’d Arrived. That’s a dangerous mindset for an artist. You don’t want to be results-oriented. Mitzi may on some level have felt that withholding the Paid Regular status was the most effective way to motivate Ari – to give him the Killer Instinct. But again, he didn’t just want his dream. He was working every day to make himself up to the task. I’ve long since shifted my mindset from being picked – as if somebody Choosing Me would on its own make me better – to being the equal of the Gig.

3. Ari was getting feedback from his colleagues and his audiences that he was good, or on his way to being good. And whether he knew it or not, Being Good was his asset. As long as people are still tuning into Comedy Central and paying money to download Louis CK specials, there’s a market for Comedy.  Ari was situated to succeed, with the Comedy Store or without it – ironically probably the main criterion for being Passed. Ari also did at least one major thing Right that a lot of artists and entrepreneurs get Wrong: he went up in front of Tough Crowds, not just Friendly ones. If you’re trying to decide whether you have Potential or if you’d better find another career field, don’t just seek feedback from friends and family. Put yourself in front of some tough crowds. The entrepreneurial equivalent is not simply sharing your Great Idea with a few friends, but seeing if Complete Strangers will pay you for it before you sink any money into it.

So, what should the person applying for a job or school program, or hoping to land a Gig, take away from this? In my limited experience it’s a combination of indefatigable persistence – often against the advice of concerned friends or relatives – with fine-tuned sensitivity to both the long-term viability of your path and how much it’s doing for you spiritually. Are you good? Is there a market for what you do? (And I’d add “can you create one”, if we were dealing with entrepreneurship.) Does it make you happy? (And one extra credit one: are the existing gatekeepers worthy of the respect their arbitrage affords them, or are there equally valid end-runs you can experiment with?)

Not sure this is a completely coherent distillation, but Real Life rarely is. Till Next Time, folks!

Travel, Identity Resets, and Action in the Absence of Fear

If it’s Monday morning and I’m on the way to work, it’s time for a breaking ferriss post. More by happenstance than by design, these posts have alternated between tactical things about business and “ethos posts” about what it “feels like” to be living this life, and things I’m thinking about. Today’s post will be the latter variety.

I’m lucky to have had to opportunity to get out of New York for at least a week twice annually for the last two years, and in every case these trips have been important “identity resets”. I don’t know if this is the case for everyone, but for me travel removes both the daily routine and the geography component. An American in Paris. A New Yorker in… So if I’m not defined by my daily routines or my geography, who am I? That’s the beginning of a really productive question. (Actually I think I am the only one I know who thinks this way about travel. For most people it’s no big deal.)

I need at least a week away, and if it’s going to be a “vacation” instead of a “work trip”, I need no access to the drums, and no requirement that I produce any business related content. The idea being to wake up in a fresh environment with no “work” to fill mental space. It can actually be depressing for the first couple of days. Workaholic Withdrawal Symptoms. Then there’s a gear-shift, and the “what am I going to do today” question starts to feel good. “From the endless list of possibilities, how will I fill my time today?”

Then the ideas start to come. You have space to think of them and time to execute them. I tested two new business ideas while in San Francisco.

The Time Abundance framework my wife calls Vacation Mode is also an important baseline. What it Should feel like to be a human being. That stress you feel at home, that expectation, that regret that you’re not living up to this or that arbitrary benchmark that’s almost certainly beyond your control, is the anomaly. That low-grade fight-or-flight feeling you’re ignoring day-to-day isn’t supposed to be there, and it’s eventually going to kill you. We think we’ll die if we don’t have as much furniture as the Williamses. We’ll actually die from worrying about it.

But there Are important things to worry about. Am I living up to my potential, or is fear or vanity or disdain for hard work keeping me in a rut? (“Hard work”, meaning work requiring stepping out of our comfort zone e.g. cold calling a client or putting our ego on the line to hustle a better job, as distinct from “busy work” that we all do to feel busy and stave off those identity questions.) What unproductive patterns do I keep repeating (key distinction – that are Within my ability to control) even though I always say I want to change them? What social relationships should I prioritize more highly? Which are unproductive?

And here’s the crux. I’ll often come up with great ideas to change and evolve my life when the “panic” seizes me on the flight back home, and as soon as I’m on the ground, in the cab, sitting on my own couch, and that panic melts away, and the gauzy comfort of routine returns, will I actually act on them? And here was the answer to my fundamental question from earlier in the summer – what mindset did I not share with “successful” people? What about my thinking needed to evolve? Once you know the steps you need to change your life (not in a destination-focused way, but in a break-out-of-unproductive-patterns way), do you still follow them when the fear of dying without conquering your fears and realizing your potential abates?

Train’s pulling in. Good time to leave it.

Monday Morning Post – State of The Business

Back on an F train commute, and ready to spew forth another time limited post.

Since I covered ethos last week, I want to touch briefly on tactics and vision in this one. Let’s revisit the fundamental question: can my business earn enough to free me from location dependence?

Let’s use Kevin Kelly’s 1000 True Fans math to see what modest success would look like, then work backward. Let’s set the quite modest goal of $1000 per month, which, to account for variability in the market, I’d boost to $1500. I currently have a $50 product for sale. Let’s say I’m earning $30 on that, after advertising and administrative costs (VA, web hosting, any cost I wouldn’t have to take on were I not running a business). To make that $1500 I’d have to sell 50 videos per month, or slightly more than one-a-day. For reasons I detailed in past posts, it’s extremely hard to get a handle on a stable conversion rate (percentage of people who see an ad who eventually buy, or, more usefully, eventual revenue that one dollar on advertising brings), that increases linearly as I increase ad spending. Instead the curve looks like an tilted parabola: the classic diminishing returns curve. Suspicion: the size of the market I’m hitting up on the platforms I’m advertising is fixed, and I have to wait for natural “churn”, as new drummers age into the target range, etc. One thing I’ll definitely do in a future business is try to get my head around the size of the market.

So while I employ methods to both increase conversion and increase traffic, I’m trying a Ten True Clients strategy in parallel. Ten True Clients is essentially ten people willing to give you $100 per month for Something. On that side I’m pitching a premium coaching course to existing customers. Fifteen “true clients” per month is another way to arrive at the target monthly min. With this course, the challenge will be making it valuable enough to command the pricetag while keeping it automated enough that I’m not just teaching private lessons by proxy.

I’ve got two pilot clients already, and my aim is to experiment with their services, continuing to add new clients, until I find the best leverage points. What’s the Venn diagram of most value to these folks with least Recurring time commitment to me. (I don’t mind spending a lot of time on a resource that will be self-sustaining once complete, for instance a lesson plan that lets students “choose their own adventure” based on how certain exercises “feel” to them, or, as a member of a mastermind suggested, a social network like LinkedIn, that would let students critique and learn from Each Other’s videos.) But first I need market intelligence, which means a small degree of virtual private teaching.

Not for nothing, I think this or next month might be the first 1K revenue month. I’m holding off publishing monthly earnings reports until them, as I’m hovering in the $100-300 profit/month range depending on ad spending. Releasing the last chapter of the series, optimizing the price point (maybe by adding some extra Evergreen features like lesson plans), and getting the coaching underway should see that number tick up. Again, the goal is Recurring 1k Profit, which is a very different beast from a good month of 1k Revenue.

Ok. Pulling into the station. See you soon!

Meta Post – On Posting

My new commute affords me more time to post on this blog. Hurray!

Challenging myself to write the entirety of a post on a short subway ride.

So what’s up with me?

Still working toward the goals outlined in the New Year’s post. (Post belonging to the new year.) Location independence. Smaller mental footprint at my day job. Mandarin. It’s important to “restate your assumptions,” as Max Cohen, the hero of Darren Aronofsky’s Pi so often does.

And just to get meta for a second, that’s why I’ve decided ultimately that writing this “personal journey” blog is beneficial, in spite of some thinkers who caution entrepreneurs to conserve their “sweet glucose” for their business. Well, I think I’ve been doing that. I created a reality show and am launching a coaching course with the help of my customers. I think I can spare some glucose for a Breaking Ferriss post.

Besides, the “conserve the glucose” canard underestimates the importance of Restating your Assumptions. Which is important to staying on target and avoiding “mission creep”. My goal is not to build a multimillion dollar enterprise to pump up my ego. It’s to free myself from location dependency and money worries, and to take action on the central premise of Four Hour Work Week, which is the insight that you can be the architect of your life. That you don’t need to take opportunities that are dangled in front of you just because they’re dangled. You can create your own opportunities.

So my business is in motion. It’s making progress toward being an earning machine, and as I make that progress I’m learning ever more about the leverage points where value is created. The apex of the Value Chain.

But the wonkier I get the less relevant this blog will be for the average reader. So I’m choosing to ruminate on some life lessons. My cognitive bias is my Fear of Standing still. The force that motivated me to leave Montana at age 18, and move to a similarly sized town to attend college at a university of similar caliber (and higher price tag). My central insight of this week? The paradox of progress is that it often requires a deep and profound acceptance of who you are at the present moment. Otherwise you’d be stuck in the trap of trying to define your identity by your progress or lack thereof, and be far more susceptible to those classic cognitive biases like loss aversion, which might cause you to miss opportunities and avoid worthwhile risks.

Make progress by accepting the present? It doesn’t seem to jibe. But consider the alternative: “I need to achieve success so I can define myself as successful.” Sure, that’s a motivator of sorts, and to a degree none of us can avoid it.

But isn’t “I accept and love myself, I’m deeply engaged in the present, and I’m taking action to set myself up for ‘success’, remembering to enjoy the journey” a lot better?

Even if it sounds like some Burning Man houey? (Never seen that word written – made a stab.)

Anyway, time’s up.

Back at you next time.

“Why” Post – Advice to Myself

Hey All – this is more of a “why” post than a “how” post.

As I navigate the waters of mastermind groups and fellow entrepreneurs, and notice parallels and contrasts with the music world and the salaryman world from my Day Job, I’ve also been listening to several interviews with Ryan Holiday, who wrote The Obstacle is The Way, the title paraphrasing a Marcus Aurelius quote that’s a tenet of stoicism.

I’ve posted this on social media, but this is really advice to myself. If it were more succinct I’d find a way to tattoo it somewhere –

1) If something seems easy, or you get a “hookup” offer from someone to whom you’re not manifestly providing value, be suspicious. Real success doesn’t smell like that. (i.e. the one job offer you get when your resume’s crappy. The person who wants to date you when they don’t know you yet.)

2) I hate the word “networking”, but making friends with people with common interests is inarguably important. I think the hack is Give Value without an expectation of reciprocity. Reach out to people both “ahead” and “behind” you, always with a pure desire to give value. (Not with the expectation of a “hookup” from those “above” or appreciation from those “below.”) This works even better in scarcity contexts where everyone wants a hookup, because you’ll distinguish yourself in a hurry.

Also, have value to give. As Seth Godin said, and as I’ve parroted here, “pick yourself”. Somebody will spot you for the last rep of a challenging weight lifting set you’ve worked up to. They won’t lift the weight for you from the beginning.

3) It’s not about you. Taking either success or rejection too personally is narcissistic. Get gigs? Product sold? It’s not because you’re awesome as a person, even though you are. It’s because you met a need. Get turned down for something, or no one wants your product? Yes, there are lessons to take and apply, but again, it has nothing to do with your value as a person. It’s not about You.

That’s it! See you soon!

Belated New Year’s Post – Goals, Perspective


Now that my sleep calendar is beginning to return to normal, and I’m starting to take stock of the life that I’ve returned to, thought I’d jot a quick post. This is mainly new goals, but it will probably take a stream-of-consciousness vibe.

Here goes:

1) Stop mentally over-committing at my job. It’s counter intuitive, but I think I can actually get more done by simply not giving a toss, and just doing my work. It’s tempting to want to do every project to the max, but that’s mental energy better spent elsewhere, and I realized over the break I was wasting a lot of energy feeling bad for not following through on “mental commitments” I’d made. Be early for meetings, finish stuff on time, yes, but give a @#$%? DEFinitely not.

2) Now an interesting one. Figure out, in the hypothetical, how I could be bi-coastal starting tomorrow if I needed to. Challenge the assumptions holding me back. Do I really need more money? No – not if I negotiated remote work for two months-a-year from NYU. It wouldn’t even have to be that, because the holidays knock out about 2.5 weeks already. Just the beginning of December and the month of January. As with other things, I could start from the premise of negotiating a raise (which, I believe, I deserve – I wouldn’t broach it if I didn’t), and know I was willing to settle for more location freedom. Housing would be the problem. But would I really need to own two houses? Definitely not. Ferriss-style, if I had a terminal illness, and a doctor told me “you need to get more sun or you’ll die“, what steps could I take to make that happen?

My wife and I discussed this this morning as a fun mental exercise. Not that it has to happen right away, but it’s fun for both of us to think about how we would make wintering in SF happen, and challenge the assumptions holding us back.

3) More mundane: break tasks into whole days. E.g. Monday, Tuesday, Thursday I’m only required to do stuff for my job. Wednesday and Friday, I’m only required to do things for my business. If I decide to do more any day for “extra credit”, great, but certainly not required. Is it about intensity, and sprints, when it comes to business? Yes, of course, but it’s also about patience and sustainability. Nothing focuses the mind like coming back from vacation with jet lag. Your brain is only useful for “smart person stuff” an expanding window of a few hours every morning, and the rest of the day it’s “don’t trouble me with trouble, man – I’m gone.” Well the upside is it forces me to structure my life so I only need to make one or two important decisions every day.

4) Increase my earning power so as to pass the “minimum happiness threshold” – where money is not a concern – beyond which more money has diminishing effects on happiness. Yes, I’m hoping 8020 Drummer, and whatever’s next, eventually are earning enough to take a chunk out of my monthly living/travel expenses. But that’s not the only way. I have a game plan to wipe out a lot of my monthly expenses by March. As Ramit Seithi (sp?) says, “don’t give up the latte – focus on the lowest hanging fruit to increase your spending power. A lot of people who never once picked up the phone to negotiate a lower rate on their power bill or long distance, or a lower credit card interest rate are going without lattes.” I’m paraphrasing, but you get the gist.

It’s unlikely I’ll get a raise at my current job, though the patently obvious fact that I’m underpaid gives me a lot of negotiating leverage in other areas. Once you’re beyond the threshold of not needing to worry about money, time is just as important as money.

4) Get seriously better at Mandarin. I don’t want to go through another Taiwan trip where I’m speaking pidgin. I don’t have to master it, but the next trip I want to see some serious improvement in my vocab and ability to read. It will make me feel better.

Notice any music ones? Me neither. I feel I’ve got the music thing dialed in pretty well, and feel like I continue to improve extremely quickly thanks to the methodologies outlined in the 8020 Drummer. I do have the continued goal to play music with my heroes and to write music, and in creative music these days, for people like me who value their time and their lifestyle, you can’t really ordain the future more than that. True, I could have a goal to go on tour with a band or something, but I can do that any time I want. In truth, if I’ve got two weeks in Japan (stay tuned;) I’d far rather not have to worry about rehearsing, negotiating pay, equipment, etc.

Ok – done and out to the world! Enjoy and happy 2014!