(or How I Barely Survived My Own Idiocy)

1) Practice Ruthless Efficiency

In my second year of running a small business I averaged 80 hours of work per week. One week I can barely remember I clocked in over 100 hours. Then I had my inevitable breakdown, lost a bunch of clients and damn near lost my business – and my shirt – in the process.

Now I work less than 40-hours per week, managing twice as many clients, with twice as many projects, while building out two spin-off businesses on the side.

What changed?

I viciously and ruthlessly removed all waste from my life, I …

I won’t lie. That fat laundry list was fucking hard to plow through. Many enemies were made. Many bad habits were quit cold turkey and triggered all flavors of crappy withdrawal.

But EVERYTHING got better. I slept better. I made my clients more money. I made more money. I strengthened all of the friendships I still cared about. I became truly happy.

Here’s a few take-aways that I wrote down during the painful purging process to keep me on the wagon:

2) Delegate Dammit.

So that 100hr work week happened due to one tragic mistake. I did not delegate ANY of my work, foolishly thinking that my profit margins would be better if I just did the work myself. But staying up till 4:30am Google’ing PHP hacks for a severely outdated Joomla plugin – well, it was fucking stupid.

Here’s why … on a $300 Project Website Tweak Project

Modifying the output of a PHP Plugin
1.5hrs for a good PHP Programmer – $75
Executed Perfectly the Next Day = HAPPY CUSTOMER
$225 Profit + Future Project + Referrals 

Learning to modify the output of a PHP Plugin the wrong way.
Duct-taping it together with flippantly pasted code.
5 hrs of work for me – $250
Poorly Executed Later in the Week = GRUMBLY CUSTOMER
$50 Profit + No More Projects + No/Negative Reference

No brainer, huh?  Apparently not for me for many years.

The sooner you learn to delegate the sooner you can take a real vacation (not the kind where you huddle over your laptop on a shaky Wi-Fi connection while in a Americanized timeshare resort on the coast of Mexico).

3) Become Boldly Uncomfortable

Anytime I’ve been lulled by a daily/weekly routine, expensive mistakes slipped through the cracks, and killer opportunities were lost. Yet anytime that I made decisions, boldly and with intention, it led to some discomfort, but ultimately led to growth.

In the spirit of the first commandment, I unceremoniously deleted 10-hours worth of work on my website, and adjusted my monthly marketing accordingly. I felt sick to my stomach. I worried that my new obsession with efficiency had bit me in the ass.

Was it a mistake?

Fuck if I know. All I know is that the current way of doing things was just okay, and a little too comfortable. If “just okay” was good enough, I might as well go get a regular job and dump my freedom and my community and my reputation while I’m at it.

If I fail, at least I know “well, that’s not it”. And if I succeed … well you know the rest.

Remember, if you aren’t occasionally failing, you aren’t trying hard enough. Period.

4) Fixate on your Existing Customers

I almost lost my business last year. In the spirit of getting uncomfortable, I decided to run my first big sales campaign. It worked really well … a little too well. In an effort to keep up, I cashed in a ton of ‘get out of jail free cards’ with my existing clients to buy me the time needed to properly care for my shiny new customers.

GIGANTIC mistake.

A month later, I was in debt with a roster of 30+ pissed off clients and a permanently tarnished reputation.

I had forgotten all the reasons WHY people do business with me.

Forgotten that my business grew organically years ago because I obsessed over each customer and each project.

Forgotten that my focus and dedication to those few led to a healthy stream of referrals.

Forgotten about the radical loyalty my clients have for me.

Forgotten about that oh-so-slippery slope into small biz douchebaggery.

After the big mistake, I humbly crawled back to my clients and gave out nearly 100 hours in free work over a three month period slowly earning back their business, their loyalty, their referrals and their friendship.

So what now?

I listen hard to my current customers. They let me know what they really want and need, what new obstacle needs removing, what new market needs reaching, what new innovation needs to be invented. And I work hard to solve the problem for them, or delegate (see Commandment #2) to someone in the community. And when they no longer have a need for my special flavor of help, they refer a ton of fellow small biz owners.

SIDEBAR: Not obsessing over your clients can cost you in other ways too. I didn’t raise my rates until a few of my clients said, “Nate, I really think you should be charging more.” Looking back on it, I’m kicking myself for not sniffing harder for this little nugget of deep fried goodness earlier in the meal.

5) Be Human

When I first moved into a ghetto attic office and hired my first batch of interns, my first goal was to legitimize my business. I created checklists, continuity guides, business plans, sales funnels, training documents, sales scripts, and created a new website with a ‘corporate-friendly’ logo and copy.

Next, I eagerly called up one of my bigger clients to tell them all about the new and improved That’s Wright Marketing (awful name, I know, but as you should know by now, I’m an dumb-ass) and sell them on some of my new-fangled “Marketing Packages”.

About 10 minutes into the conversation, he harshly interrupted me, and said, “Nate, what ARE you talking about? I just need more customers like yesterday. Is this supposed to help me”.

It took over a year for that free lesson in humanity to sink in. It wasn’t until I was two pitchers into a late night hang with my overly-honest friend Drew Dundon, that he issued a challenge to me, “Just try getting away from that damn laptop, and get in front of actual people. You’ll make more money”.

So after suffering through my own mistakes, I caved and implemented Drew’s ‘in case of emergency break glass’ plan. And things got better. Way better. And I realized why my clients continue to bring me business.

They do business with me because they like me. They like my ragtag group of freelancers because they are like me. They like my services because they are delivered in a style birthed by me.

And who am I?

I’m a cranky, stubborn, egotistical, aggressively honest, hyper-sensitive man with poor attention to detail and no formal training. So why do these people keep hiring me?

Because I TRULY care about their success. I don’t leave projects un-finished. And I never, ever let them pay for my shortcomings or mistakes along the way.

And you know what? I like them too. Because they are (nearly as) flawed as me, and care about what they do more than anyone else, and desperately want to finish smaller things so that the bigger things can get better.

6) Build a Community of Doers (not an Audience of Spectators)

I’ve built many communities over the years. A few succeeded. Most failed.

When I moved to Seattle in 2006, I attempted to build a community of working musicians. I brought together interesting acts, duct-taped all of their individual marketing efforts to bring in better gigs, forged relationships with non-musicians that were passionate enough about the art form, pulled together epic hangs, organized tours, negotiated better payment with venues. And for awhile it was great. Everybody knew me. I knew everybody. I felt cool, not like some recovering geek with shattered self-esteem, which was dramatically closer to the truth.

Now it’s 2012. That community rapidly died shortly after I transitioned into my current life, and not even a scrap of what I helped build remains. It’s depressing.

The most successful community I built was entirely by accident. I eagerly jumped into the swing dancing fad back in the late 90’s. My dance partner and I started teaching a few college students in the dorm hallways and organizing small dances. Within a year, we had to borrow a ballroom to hold the 50+ students that came in weekly, and ran dozens of events that hit max capacity.

Much of that community still remains.

So what’s the difference?

The music community truly needed help, and were humble enough to accept it. But most of the people involved were not willing to make even a small change, experience even the slightest discomfort to their routine. They just watched as others like me tried to manufacture a glue strong enough to hold them together and make things better.  When I left the community it just stopped growing, and over the years has shrunk down in size and devolved into a scattered mess.

The dancing community was built of doers. People that could only participate by getting uncomfortable and making a decision to power through the discomfort until they could experience the dancefloor had to offer. And when they experienced it fully, they HAD to bring all of their friends too. And when we started carving out new territory, everyone understood that to continue experience the good shit, they had to actually work. Moving chairs, humping flyers, making dozen of phone calls between classes.

I didn’t make a dime off that community, but some of the purest and happiest moments of my life transpired on the dancefloor. And I’m sure if I had something to sell to that group, that they would buy it without hesitation.  When I left that community in 2000, it kept growing in my absence.

The world doesn’t need anymore window shoppers.

When you start obsessing over your existing customers, you’ll invariably find that your favorites are the doers. They belong to that shrinking club of people that just – get – shit – done. They’ll let you know when something is wrong, they’ll applaud you when something goes right, they’ll pay you on time, and refer you enthusiastically.


I chose to become a small biz owner because I wanted a better lifestyle.

Now, there are plenty of hella smart and wickedly successful people out there who perhaps have a better way of handling the challenges I’ve clumsily encountered and muscled through. But this long ramble is not for them.

This is for the survivors. The ones that still get scared, and regularly fuck up, and struggle with the day-to-day.

The people like me.

I doubt if any of the shit I spewed above is going to change your life … but it might buy you enough time to catch your breath and buy you another day of the delicious freedom this crazy lifestyle we chose brings.

Hope you enjoyed it … this started as a simple to-do list and turned into a frigging self-aware monster. 




– Nate Wright –
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P.S. Special thanks to Gary Vaynerchuk, Derek Sivers, Seth Godin, Jason Fried, Ludlow Chang, Debra Lowell, James Chartrand, Ramit Senthi and Robert Bruce for sharing all of the wonderful advice which inspired the business / life changes above. Also a big shout-out to Eric Fridrich, Billy Gold, Drew Dundon, Marti Bering and Seth Rasumussen who patiently weathered the storm caused by my drama-ridden self-improvement campaign these past four years.