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Summer of Love (Handles…and Getting Rid of Them): Summer 2015 Monthly Challenge

Posted in 2015 Monthly Challenges, Habits, Personal, Posts by

For background on my monthly habits + experience thing that I’m doing for 2015, check out the post for January. You can also read about February, March, April, and May.

Positive habit: Tracking food every day
Negative habit: No eating out by myself
New experience: N/A

Up until this point in 2015, I’ve been doing two new habits + a new experience every month. However, we have a new baby in the house, we moved over the summer, and we’re facing some financial and time crunches due to several other situations.

As a result, I decided that I’d combine the summer into one big chunk of time and do my habits and experience for the entire summer, rather than by month, and then resume the monthly schedule starting in September.

Also, an important note: I decided to do this at the end of June. I had picked my June habits already and when July rolled around, I decided to just keep doing them for the summer. Wish I had it more together, but I don’t :)

When deciding what I was going to do for my habits for June (and then the whole summer), I wanted to pick things related to losing weight. Over the last decade, my weight has gradually crept up on me, just a pound or two per year. It wasn’t something I was overly concerned about, but then at the end of May 2015, I happened to jump on a scale at the gym and I was horrified to see 210 lbs on the scale.

Two hundred and ten freaking pounds!?! I had spent the last few years in the 195 – 200 range, mostly closer to 200. But of course, I think of myself as basically 195. That’s what I put when I have to put my weight down. The mental barrier of 200 was too much for me. Now I’m staring at a scale showing me at 210. What happened?!?

Like most people who make a positive change in their life, I had one of those “that’s it!” moments where I determined that things were going to have to change. It was with this mindset that I went into June, and so I chose habits to reflect that.

Positive habit: Tracking food every day

There’s no mystery to how I ended up at 210 pounds. As Kelly Starett says: “I eat like an asshole.” I treat my body pretty poorly in terms of both diet and exercise and it’s catching up with me.

You know the saying “garbage in, garbage out?” Well, in this case, it was “garbage in, your body now looks like garbage.”

So first thing was to clean up my diet, and the most effective way I’ve found for that (and a lot of other things) is to measure.

I use MyFitnessPal to track all the stuff I put in my face every day, and it’s often pretty dismaying to see in black and white.

For example, I love chips. But yeah, a handful of chips is like 7000 calories. And they’re not even good, healthy calories. So I don’t really eat chips as much anymore. And if you love salad, I hope you don’t love olive oil, because it’s approximately 11 bajillion calories per drop.

My goal was just to track my calories and try and stay below the target calories each day. I didn’t worry too much about the macronutrients at this point (how the calories broke down between fat, protein, and carbs), partly because I didn’t want to get analysis paralysis, and partly because I didn’t need those numbers for my purposes. I’ll need those in the long run once I start lifting heavy again, trying to maintain a long-term balanced diet, etc. But for now, tracking nothing but calories was enough, and the data in MyFitnessPal is more reliable for that than macros anyway.

Pretty quickly, my behavior started to shift.

For one thing, you start to get a feel for how many calories everything you eat is going to be. I suspect that you could track your food religiously for a few years and then never do it again and probably be fine, because you have an innate sense at that point for what you should and shouldn’t eat, and how much, etc.

The next thing to happen is that you start to think about the rest of the day and how your food intake is spaced out, etc. If I only have 2000 calories to eat today and I have a 1200 calorie breakfast at 6am, it looks like I’ll be having huge bowls of spinach for lunch AND dinner.

I also weighed myself every day, first thing in the morning, and wrote the numbers down on a whiteboard. The numbers fluctuate around a little each day, but the overall trend each week is definitely down. And I found that really encouraging.

I set aside Saturdays as a cheat day, when I didn’t have to track or worry about diet. This was really helpful psychologically throughout the week, because I didn’t have to think about the prospect of giving up pizza forever or something stupid like that. I just had to wait a few days.

I really went overboard on my first few cheat days. I suspect I hit 5000 calories on several of them. I know that sounds insane, but if you get a giant fatty bacon cheeseburger with a thing of fries and a large shake, you’re probably already pushing 2500 – 3000 calories.

Things settled down a bit later in terms of cheat days, but in retrospect, I think the cheat day thing would have been better as a cheat meal. I think I’ll switch to that in the future.

Now, I definitely wasn’t perfect throughout the summer. I neglected to track many days, and went over my calories many days. But I still made great progress, going from 210 lbs down to 193 lbs. There’s a caveat to that number, which is that the 210 lbs was at a gym while traveling and I never got to use that scale again. Based on the numbers I was seeing a few days later on my own scale of more like 206-208, I suspect that it was reading a little high.

So I probably lost more like 14-15 lbs, not 17. I’m ok with that. I think I could have lost 20-25 pounds over the summer if I had been a more disciplined, and that would have been great, but the overall, long-term goal here isn’t some specific number by a specific day, but rather a switch to a healthy lifestyle.

Grade: B-

Addendum: I’m writing this in late Sept 2015, and I’ve definitely fallen off the tracking wagon and lost a couple pounds of the progress I made. There are few things more powerful in life than steady, measured progress every day towards a goal, and I’m going back to it starting today. 590 calories consumed so far today.

Negative habit: No eating out by myself

I don’t know that eating out is a “bad habit”, but it’s connected to some bad habits for me.

For starters, a slight majority of the unhealthy eating I do is while eating out, not while eating at home. Probably because I can’t make taco bell at home. Yeah, I know, disgusting. The portions are bigger too.

Another bad habit is just the money I spend eating out. I don’t mind cooking every now and then, but I hate eating every meal at home. The hassle, time, and monotony is a huge pain point. If I could, I’d have a personal chef, but instead I just eat out all the time. And that adds up, to easily thousands of dollars per year.

Finally, unless you’re eating at a chain restaurant, it’s surprisingly difficult to accurately track your food intake when dining out.

So basically, eating out for me is spending money I shouldn’t on food that isn’t good for me, and not having a good idea of just how bad for me it is.

I considered making my habit just avoiding eating out entirely, but that felt like I would be throwing out the baby with the bathwater.

Sharing a meal with others is one of life’s greatest joys and opportunities for connection. And depending on the situation, it’s often difficult or impossible for those occasions to take place at someone’s home. My wife and I have a standing engagement every week to spend out together, I meet new and interesting people for coffee or meals constantly, including while traveling, etc.

So I decided that rather than avoid all eating out, I would just avoid eating out by myself.

This actually turned out to be surprisingly easy. I think a big part of it is having a baby now. We just spend more time at home naturally, and that’s a big help.

Also, I also think that I’ve made more of an effort to find someone to go to meals with. Part of that is moving to a new area, and trying to get to know people and the food scene in that area, but I think it also might be a subconscious hack to eat out more :)

Finally, I also included this rule in my Saturday cheat day exception, so Saturday around noon would often find me alone at a local pizzeria, stuffing my face with an ungodly amount of food. #noshame…#okalittleshame

At any rate, having this rule on the other six days of the week has definitely contributed to a healthier budget and to the weight loss I talked about above.

Grade: B+

New experience: N/A

I’ve been thinking a lot about great writing lately, and what makes it great. I think a big part of it is vulnerability, and I want to emulate that, but wow, it’s hard.

I had several ideas for a new experience to do over the summer, and I could have found the time and money for them, but truthfully, I just got lazy and let the weeks roll by.

In general, I find the habits much easier to do than the experience. The hardest part of the habits is picking them and then doing them for the first few days. After that, they’re basically locked in.

But the experience is much harder. Even though it’s only one chunk of time in the entire month, it’s just so easy to let the month slip by without finding any time for it.

It’s embarrassing to me to write this, and though I’m not proud of this, I spent some time before writing this trying to think of something I could say that I did as my experience. But sadly it was a boring summer in terms of new experiences worth writing about.

But that’s just dumb anyway; I didn’t do it! The whole point for me of writing is self-discovery and trying to share the things I’ve learned. It doesn’t make any sense to try and hide those things from the world.

So sorry, no experience this summer.

Grade: F


Well, there you have it. More than you ever wanted to know about the things I did (and didn’t do) this summer.

I feel pretty satisfied with my progress towards a healthier weight, although I’d like to get it down closer to 185 lbs. I think I could have gotten there by now if I hadn’t let the tracking slip for the last few weeks in particular.

I think the only thought I’d like to leave you with is the idea that perfection isn’t the goal: progress is. There are few things more powerful than momentum. Get started before you feel ready, and make small progress every day. It doesn’t matter if you start in the wrong direction, or if you make the most infinitesimal progress every day. You’re going to get frustrated, you’re going to make changes, you’re going to figure it out.

The important thing is to start.



Positioning Pomodoros, Popsicles, and Pedaling: May 2015 Monthly Challenge

Posted in 2015 Monthly Challenges, Goals, Habits, Personal, Posts by

For background on my monthly habits + experience thing that I’m doing for 2015, check out the post for January. You can also read about February, March, and April.

This was my most boring month, but I’m including in here for completeness.

Positive habit: Spend a 25 min block of time (pomodoro) on positioning my business
Negative habit: No buying popsicles
New experience: Use a bike as primary method of transportation

Summary: Just skip this post and come back for June, which will be better, I promise.

Positive habit: Spend a pomodoro on positioning my business

Grade: C

I run a solo consulting firm and I’m currently a participant of a six-month workshop run by Brennan Dunn. The goal is to increase the size and quality of my client engagements, and one of the most important steps in the process is positioning. The basic idea is to pick a smaller niche to focus on. So instead of “I develop mobile apps”, do something like “I help luxury hotels grow customer lifetime value through mobile marketing” or “I help develop sales leads for over-the-road trucking companies in the Northwestern US”. Most freelancers are generalists and market themselves that way, because picking a tiny niche is really scary and difficult, but it’s dramatically easier to close leads in that niche if you do. I’d highly recommend “The Positioning Manual for Technical Firms” by Philip Morgain if you’re in this situation and want to learn more.

Anyway, I wanted to spend about 30 mins of focused time per day researching different niches and trying to select one. Unfortunately, I didn’t spend as much time on this as I should have. I did make progress, but it wasn’t anywhere near 30 mins per day. I’m giving myself a C on this one. The good news is that I’ve kept working on this throughout June and I’m continuing to make progress.

Negative habit: No buying popsicles

Grade: B+

Ok, I know this seems stupid, but I’m addicted to sugar-free popsicles and I eat way too many of them. I decided I wanted to just not buy any this month. I did end up buying some a couple days before the end of the month (I forget my excuse) but that’s a dramatic improvement, so I’m giving myself a B+ :)

New experience: Use a bike as my primary method of transportation

Grade: A

As I mentioned in a previous post, I live in NYC, which means that the subway, cabs (and Uber), and my feet are the primary forms of communication. However, when I lived in Portland, bought a bike, which I dragged with me to NYC, but I broke a spoke a few months after we moved here, and the bike has been sitting idle for the last couple years. I finally decided it would be nice to ride it in the park, so I got it fixed and got a tune-up.

However, I further decided that it would be nice to use it as a primary form of transportation, especially to get to my office. So for the month of May, I rode my bike down through Central Park in the morning, and then down 9th Avenue through Midtown to my office. Not too bad, since there’s a bike lane on 9th Ave with a row of parked cars protecting you from the traffic:


Credit: nycbikemaps.com

However, coming back home took me up 8th Ave, which has large sections without such a bike lane, and about a billion rush-hour pedestrians clogging what bike lane there is. Then you have to navigate the swarm of aggressive cabbies and angry drivers stuck in traffic after working a long day in Midtown. I would end up weaving between cars and pedestrians with only a few inches to spare, sure I was going to be run down any minute.

Suffice it to say that if I had done this for the three years I’ve lived in NYC, I’d probably be dead. My deepest sympathies to the bike delivery folks out there for the dangers you have to face.

Other than that, I think I’d use a bike as my form of transportation more if I had a good solution to the “arrive at work sweating profusely problem”. They seem to manage somehow in Amsterdam, but I haven’t figured it out.

Still, it was a decent experiment, though not really the kind of monthly experience I had in mind when I started this year.

Again, June will be better.



Gratitude Journal, Media Fast (again), and Having a Baby: April 2015 Monthly Challenge

Posted in 2015 Monthly Challenges, Goals, Habits, Personal, Posts by

For background on my monthly habits + experience thing that I’m doing for 2015, check out the post for January. You can also read about February and March.

So mainly due to the new experience for this month, I didn’t want to push it in terms of trying to do too much:

Positive habit: Write down three good things that happened that day
Negative habit: Media fast (yes, again)
New experience: Having a baby

Summary: mixed bag on the habits, still one of the best months of my life.

Positive habit: Write down three good things that happened that day

Grade: A

I heard about this idea from James Altucher, and it seemed interesting. So I now keep a notebook and pen right by my bed, and every night, I draw a line across the page under the last entry and jot down the date and three things that were delightful that day.

You’ve probably heard of this as a gratitude journal, and I guess it is (as I’m grateful for all these things), but I really just write down three things that I enjoyed or that were the highlights of my day. They’re often really minor things (like a great snack or a short breezy walk through the park), but things that I enjoyed nonetheless. I actually found this really easy and positive. I didn’t miss a single day, including weekends, though I did forget a few times and do it the next morning. I’m writing this in June, and I’ve kept this habit up for the last two and a half months. It only takes 2 mins and is a very nice way to end the day on a positive note.

Side note: I was really surprised to see that I had something food-related almost every day. I wouldn’t have expected that…no exclusive Soylent diet for me, I guess.

Negative habit: Media fast (again)

Grade: F

If anyone is keeping track, yes, I already did this one, back in February. I decided to redo it because I got so much out of it the first time, but I had fallen back into watching too much TV during March, and I was hopeful that I could shift my TV time to book reading time (since I’m attempting to read 100 books this year) while taking care of baby (see below).

However, I drastically underestimated how much willpower depletion would get to me due to sleep deprivation. It’s just so much easier and more attractive to watch a stupid TV show than to read a book the middle of the night.

I think I probably set some new personal records for Netflix during the month of April. Easily the worst I’ve done on anything during the monthly challenges. Yes, I failed to go ice fishing, but I had a good reason and I didn’t just completely ignore it.

New experience: Having a baby

Grade: A

Ok, this one is cheating, partly because it’s not something I planned to do because of the monthly challenges, and partly because (as my wife would be quick to tell you), I didn’t do it. :)

However, in terms of things that everyone should experience once in their lifetime if they can, it’s hard to top seeing your child come into the world.

Not much to say about this one here, except that everything went very well, and that the birth and the ensuing two months have been some of the best of my life.

But that’s a story for another time.



Walking, Going to Bed Early, and SxSW: March 2015 Monthly Challenge

Posted in 2015 Monthly Challenges, Goals, Habits, Personal, Posts by

For background on my monthly habits + experience thing that I’m doing for 2015, check out the post for January. You can also read about February here.

So February didn’t go quite as well as January in terms of the monthly challenges, but I decided to press on. I decided that for March, I’d do the following:

Positive habit: Take an hour-long walk every day
Negative habit: No staying up after 10pm
New experience: Go to SxSW Interactive in Austin

Summary: this month went much better than the disaster that was February.

Positive habit: Take an hour-long walk every day

Grade: A

I’m fortunate to live in NYC, easily the most walkable city in America. We actually do own a car here (an unheard of luxury, and probably stupid of us), but we never use it to get anywhere in the city. Like everyone else in Manhattan, we either take public transportation or we hoof it.

So I do a lot of walking already, but most of my walking is transportation walking. I’m trying to get from point A to point B as quickly as possible. And because I’m in Manhattan and it’s March, it’s freezing cold, and crowded, and I’m stressed out with work and finances and everything else, so I’m not enjoying it at all.

And that’s a shame, because walking is one of life’s great pleasures.

So for the purposes of health and sanity, I decided to take an hour long walk every day. Not walk for an hour total every day (easy in NYC) but actually go out for a walk for an hour. And although it’s cheating (since it’s transportation from point A to point B), I did a lot of my walking from home to work or vice-versa.

I’m fortunate to live right by Central Park, and as my office is in midtown, almost two miles of my three mile walk to work are through or along the edge of the park. So for the month of March, I spent many days walking to or from work, cup of hot coffee in my hand, podcast or audiobook in my ears, looking at the beauty of Central Park or the buildings that line Central Park West. It was really very pleasant. I caught up with family and friends, listened to music, or just walked and enjoyed the city around me. I remember arriving at my office feeling so invigorated, like I had just had ten cups of coffee.

Not only is this one of the best habits I’ve done so far this year, but I also easily kept up with it, so I’d give myself an A on this one.

Negative habit: Not going to bed after 10pm

Grade: B-

I’ve written posts before about my ongoing journey from night owl to early riser, but like many habits that attempt to overcome a fundamental aspect of personality, this isn’t something that has magically transformed for me. I think that as long as I live, I will naturally stay up late and get up late.

Over the last year or two, I’ve become less consistent with my early mornings, so I wanted to improve the situation, and one of my key realizations about becoming an early riser (indeed, with many of my habits and life goals) is that the critical thing for me is not getting up early, it’s going to bed early. If I go to bed at 9pm, getting up at 430am is easy, and getting my daily habits done is easy, and working out is easy, and so on and so forth.

Almost nothing puts my life on the right track on a daily basis like going to bed early.

So I decided that for a month, I would try to go to bed no later than 10pm. I often stay up until 1am or 2am, so 10pm was a shift.

I would give myself a B- on this one. I did pretty well, but there were definitely a few nights when I completely ignored this in favor of staying up.

In retrospect, I should have made 9pm my cut off time. Oh well :)

New experience: Going to SXSW

Grade: A

If you’re not familiar with South by Southwest (SxSW), it’s a music, film, and interactive conference that takes place in Austin every year. The interactive portion was what I was especially interested in. It takes place over 5-7 days and has panels and talks on every conceivable subject related to technology. I had wanted to go for years, but never got around to it. But one of my goals this year is to dip my toe into the conference world (I’ve gone to two so far this year), and this seemed like a good place to start. I also had never really been to Austin either, and I heard it’s a great town.

SxSW was awesome, I really enjoyed it. I learned a lot, was inspired, met some great people, had a relaxing time, and I’ll be back. I’d like to speak at SXSW next year or 2017, but we’ll see. :)

I’ll post the results for April soon!


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Writing, Media Fasting, and (not) Ice Fishing: February 2015 Monthly Challenge

Posted in 2015 Monthly Challenges, Posts by

For background on my monthly habits + experience thing that I’m doing for 2015, check out this post. You can also read about the habits and experience that I did in January. I wrote this post about a month ago, but am just now publishing due to other things going on :)

Fresh off the success of my meditation and not drinking any alcohol for January, I decided that for February, I’d do the following:

Positive habit: Write something substantial every day
Negative habit: Media fast (except books)
New experience: Go ice fishing in Vermont

Summary: this month did not go as well as January did :(

Positive habit: Write something every day!

Grade: C-

For years, I blogged basically every day. But two or three years ago, I just got too busy and stopped cold turkey. I always found it easier to blog every day than to do it occasionally. Same with working out, actually. At any rate, anytime I start writing every day, I find it very difficult for the first few days, but then it gets easier. And then after a few weeks, I start thinking of things that would make for interesting posts all the time.

So I wanted to get back to that level of mental creativity, but one thing that I’ve always disliked about my blogging is that writing great content every day is almost impossible, so I end up with a bunch of mediocre posts with the occasional gem. So instead of making my goal to publish every day, I wanted to do one of the following:

  • Publish a blog post
  • Write 1000 words
  • Write for an hour

My thinking was that I could spend more time really going deep on a topic, or maybe just spend an hour editing a post, etc. Also, I didn’t restrict it to blog posts, as I have a mountain of other things that need writing for various projects and initiatives.

Well, it didn’t go that well. I did post a few blog posts, and I spent a bunch more days editing those posts or others, and still more days working on other writing projects that have yet to see the light of day. But I probably hit my target fewer than 50% of the days of the month. Pretty dismal. It got worse towards the end of the month, as I got more demoralized about how poorly things were going.

I think the only good news here is that it did get me to write a few posts and I’m thinking more about writing somewhat frequently and how I can make that happen.

So, giving myself a C- on this one.

Negative habit: Media fast

Grade: A

Like a lot of people, I consume a metric ton of media. I follow a couple dozen TV shows, regularly listen to 10+ podcasts (mostly weekly), and spend too much time reading Reddit, Hacker News, Google News, Quora, etc.

Now, there’s absolutely nothing wrong with entertainment…and some of these things (the podcasts and some of the web surfing) is generally educational and mentally enriching. But I find that I crave it all so much, and I think it often impacts my ability to focus and enjoy slower things. At any given time, I have roughly 11 billion media choices available to me 24/7.

One of my goals this year is to read 100 books (lost some ground this last week, but generally on track so far), which means I need to be reading two books per week, finishing a book every 3.5 days. That’s very time-consuming, even if you’re using Kindle + Audible to get reading time in everywhere possible.

Combine that with wanting to spend a lot of time writing every day and I knew it was going to be almost impossible to keep up with everything if I kept my media consumption levels where they were previously. So I decided that doing a media fast this month would be a good idea.

The rules were simple: absolutely NO media other than books (paper, kindle, and audio) or instrumental music. No TV shows, no movies, no web surfing for entertainment, no news media, no podcasts, and no non-instrumental music.

My goal was to really clear my mind and be able to stretch my attention span to be able to read for a couple hours every day without feeling bored or restless.

When I’ve done media fasts in the past, it’s always been really hard for the first week or so, and then it gets easier, once my brain adjusts.

For whatever reason, this time it was basically easy from day one. I don’t think I “cheated” at all, though there were a couple times when I opened a website before remembering the fast and closing it.

I really can’t express the clarity and peacefulness that doing a media fast like this brings. There were a few times, mostly towards the end of the month when I wanted to watch a TV show, particularly while preparing food, but overall, I felt like I had a tremendous amount of time and mental attention available.

I will say that this is so much easier to do successfully if you have a really good book that you’re reading that’s fun and entertaining, not a slog that you’re reading because you feel like you should. That’s fine too, but for moments of high willpower, not low willpower.

So I’ll give myself an A for this one.

Side note: after March 1st, I returned to consuming all these forms of media and I have very mixed feelings about it. A big part of me wants to continue the fast, particularly with 90% of the tv shows, podcasts, and web surfing. They’re entertaining, but in a fairly shallow way. I just don’t think my well being is being improved by them.

And in some cases, just the opposite.

I can remember a couple of distinct times when I watched something that made me envious or feel guilty about something I should be doing, and thinking: “Wow, I haven’t felt like that in a long time.”

The stuff we put in our brains influences us more than we think it does, and I think we could all stand to be a bit more conscientious about it. But enough rambling about that. :)

New experience: Ice fishing

Grade: F

I didn’t do this one. We went to Vermont (the trip was a total disaster, but that’s another post), but we decided that ice fishing wasn’t in the budget. I resolved to come up with another experience to replace it, but I ran out of month before I came up with anything.

However, I’ve already done TWO new experiences in March to make up for it. :)

So to summarize, I had a very successful media fast, but did poorly on writing every day, and didn’t do my new experience at all.

Looking back at past years when I’ve resolved to do something new for the year, February is often the time when life intrudes to the point that it drops off, so I think this slump was expected, but I’m happy that I didn’t give up totally, and things are going much better in March.

More about that in a few weeks!

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My Year in Review for 2014

Posted in Personal, Posts, Year in Review by

san-diego-sunsetGotta love California!

A few of my favorite bloggers do annual “Year in Review” posts that are some of my favorite things to read (read these three to get a feel: Patrick, Brennan, Amy). What makes them so enjoyable for me is that it pulls back the curtain for me on their entire world and how the pieces all fit together, their triumphs and their failures. I suspect they don’t do it more frequently because that kind of honesty and vulnerability is draining.

I’ve been meaning for years to start doing these types of posts myself, and I decided recently that I’d better start soon or I’ll die waiting to begin. So even though this is six or seven weeks into the year already, I hope you enjoy.

A little background may be necessary.

My wife Alexis and I live on the Upper West Side in NYC. We’re both self-employed and have been since 2007. She does social media and content marketing, and I do mobile application consulting and development. I also started a tech company in 2010 (ugh, didn’t realize it had been that long ago) with a friend.


Almost doubled consulting revenue, hired a coach, went on three cruises (for work), bought a profitable SaaS business, traveled a bunch, screwed up my knee, and one more thing.


Note about terms: I used to refer to myself as a freelancer, but I hate that term now. What I actually do is contracting, but I refer to myself as a consultant for aspirational reasons.

I did web development for the first few years of my freelance career, and about five years ago, I switched to doing mobile, specifically iOS development.

I love it. I help startups and midsize companies (and the occasional very large company) plan, build, and grow mobile applications to support their business goals. Over the years, I’ve gotten to work on some very fun projects with some very talented people.

I was blessed to have another amazing year in 2014. Revenue was up 91% year-over-year from 2013, and thanks to the magic of solo consulting with very low overhead, very little of that is lost to expenses. I did hire more subcontractors in 2014 (more on that later), but most of that revenue I’ll get to keep (and pay taxes on, ugh).

I’ll say it again: if you want to dramatically grow your income, it’s worth considering working for yourself. It took me longer than it should have to get here, but now that I’m here, my income is growing dramatically every year, much faster than it would it almost any job or career other than self-employment. If you’re interested in this and would like to talk more, email me. I’m not selling anything, but I love helping people take the first step on the road to owning their own time and success.

Sometime in 2013, I started taking a serious look at my business. Until then, I had thought of myself (and behaved) as a freelancer, and this was just a way to make some money on my way to somewhere better. I enjoyed the work, but I didn’t have much of a system for getting it, performing it, etc. Reading “Double Your Freelance” in late 2012 was a turning point, and then in summer of 2013, I took a recurring revenue workshop put on my Patrick Mckenzie and Brennan Dunn that started to dramatically shift my thinking about my business.

By early 2014, I was beginning to do things differently, and that trend continued and accelerated throughout 2014, to dramatic results.

I hired an intern developer to help with some of the programming tasks that don’t require a lot of expertise. He’s a solid developer and I direct and review all of the work he does, but it frees up a lot of my time to focus on the really valuable thing I do for my clients, which is leverage technology to solve their business problems effectively.

I also hired a virtual assistant, which I’ve done before with mixed results. This experiment is ongoing, and while my VA is great, my big problem is finding things to pass off to her. But the list of things is growing and I’ll hopefully have more to report here in 2015’s end-of-year post.

In one of my more interesting experiments, I went on three different week-long caribbean cruises by myself in 2014, solely for the purpose of getting work done. I know it sounds ludicrous (and it felt ludicrous every time), but cruise ships are now one of my favorite places to get work done. I have a whole post about this that I’m writing up, so if you want to hear more, be sure to subscribe to make sure you don’t miss it.

Finally, I hired Brennan Dunn for six months as a business coach, which basically consisted of weekly calls to review my business, discuss challenges, and figure out next steps to get to the next level. I got more than enough out of it to be worth it, but less than I was hoping. However, that’s entirely on me, because I didn’t execute on the things we talked about as well as I should have. I’m working hard to rectify that in 2015.

Conclusion: had an amazing year of contracting, started the switch to building a consulting business, and am already seeing results. My goal is to double my revenue again in 2015.


I started a company in 2010 with a friend, and we went through an incubator in Portland, OR. We had an amazing experience and eventually moved the company with us to NYC. I’ll spare you all the details, but from 2010 to 2013, we changed the business 2-3 times, looking for the right product-market fit. The business was doing OK but not great financially and in terms of growth, and by mid-2013, we were experiencing enough success from our consulting work that we decided we needed to significantly shift our thinking with DailyPath or just shut it down and focus on consulting.

So we shut down the DailyPath businesses and started searching for a profitable startup to buy that had a business model and growth profile that better fit our needs. Essentially, that meant that we wanted to buy a business that:

  • had other businesses, not consumers, as its primary customer base
  • made money by selling software on a monthly subscription basis (the SaaS model)
  • was making at least $1000 / month in revenue
  • charged at least $50 / month for the lowest-priced plan
  • could be purchased for less than $20,000 (we ended up paying much, much more)

Basically, our goal was to find a side project for a developer or small agency that had demonstrated some degree of product-market fit and potential (read: had revenue), but needed technical and marketing expertise to take it to the next level (read: not a lot of revenue). I’ll write more in the future about why we had these criteria in mind, and a few new ones that I will definitely add to the list when I buy the next one.

(Incidentally, if you know of a small tech company for sale that fits some or all of these criteria, please contact me immediately. Not only am I in the market myself, I know several people with their checkbooks out ready to buy something like this.)

We searched for months for a good fit and we ultimately bought something quite a bit larger than we had first set out to find, but I’m very satisfied with what we purchased and how the ensuing year of operations has gone. I’m not yet ready to talk publicly about the company, but we’re hard at work on a big version 2.0 relaunch, at which time I’ll provide more public details.


On the personal side of things, Alexis and I finally got our act together and started seriously budgeting and sticking to it. We created this list of budget rules that hangs on our fridge, and with the exception of a couple months in 2014, we’ve stuck to it. It’s made a huge difference in my stress levels about money, though more income helps too (seriously, email me about making more by being self-employed).

We celebrated our tenth anniversary in 2014 and took an amazing trip to St Lucia. We also spent a very fun week in Mexico with friends from San Francisco. Unfortunately, I messed up something in my knee running on the beach there and it’s been plaguing me ever since. I keep putting physical therapy in the budget every month but I haven’t gotten around to actually going. Stupid.

We moved from our one-bedroom apartment into a three-bedroom apartment that we got an amazing deal on. We also bought a car, which is unusual in NYC. I love the city, but I also love getting out of the city and having a car makes that so much easier.


In many ways, 2014 was the best year I’ve ever had, both personally and professionally. Alexis and I both grew our businesses significantly, acquired a new business, traveled, celebrated our tenth anniversary, got a great new apartment and car, grew closer with a fantastic group of friends in NYC and beyond, and got our personal finances in shape. A few things didn’t go as well, mostly in the area of executing on plans I had, but I’m much more focused on execution in 2015.

I’m pretty sure 2015 is going to be even better. Part of that is my general sense of optimism and the way the first couple months of the year have gone, but mostly, it’s because of one more thing I found out in 2014 that I haven’t mentioned:

It’s a girl!




Calm, sober, and freezing: January 2015 Monthly Challenge

Posted in 2015 Monthly Challenges, Goals, Habits, Personal, Posts by

So what’s this “Monthly Challenge” thing?

We spend a few days around Christmas every year in the mountains of Colorado with family. I try and use this time to think all my breathtaking and dramatic thoughts, because hey, it’s a breathtaking and dramatic environment:

Summit From Above photo
Photo by Zach Dischner

Anyway, I think about the prior year and all I experienced, failed at, accomplished, and learned (I’ll have a “2014 year in review” post up soon). I also try to think about what I want the next year to look like, though I don’t really set much in the way of annual goals.

I love daily habits but my list of habits is already too long (I think I’m at 13 or something), so I decided that for 2015 I’d do some little monthly experiments, basically trying out new habits for a month at a time.

And probably due more to indecision than ambition, I’m doing three things every month as part of this “Monthly Challenge”:

1. Positive habit – this is where I do something every day. Unlike my normal daily habits, I also do this on weekends. In January, this was meditating every day.

2. Negative habit – this is where I avoid doing something at all. In January, I avoided all alcohol.

3. New experience – I have long lists of things that I’d like to try at some point, from archery lessons to bungee jumping to sensory deprivation tanks. I decided to pick one every month and try it.

January Review

To kick the year off, I wanted to start with relatively easy habits, so I picked daily meditation and avoiding alcohol. For my new experience, I decided to try whole body cryotherapy (What the hell is cryotherapy, you ask? Keep reading!).

Positive Habit: Meditation

I had recently heard several people extolling the benefits of meditation, and specifically mentioning an app called Headspace that made it easy to get started. I’d been curious about meditation for awhile and I wanted to start with something relatively easy for January, so this seemed like a good fit.

The Headspace app is well designed and really does make it easy to get started. You start on a program of 10 minutes a day for 10 days. It’s guided meditation, so you have someone telling you what to do on your headphones, and you just follow along. It’s also got great animations like this:

Now, you might be thinking:

“Meditation, Ryan? What’s next? Are you going to shave your head and go on a spiritual retreat to India?”

You’re not alone; I think many people are turned off by meditation because they imagine something like this:


But don’t worry, there’s nothing spiritual or weird about the style Headspace offers, basically just about relaxing, breathing exercises, and focusing the mind.

I found it interesting the first few days, and then increasingly boring and frustrating for the next few days. I finally figured out that it goes about 100x better for me if I do it in the early morning, soon after I wake up. If I try it later in the day when I have a million other things that I should be doing, I can’t focus and end up feeling even more stressed.

So after I got into the swing of it more, things went much better. Looking back and reflecting, I think I’m going to keep it as a daily habit for now. I can’t point to anything specific it has improved, but I feel a tiny bit more peaceful and focused. We’ll see how I feel after a year or two of it, but at its best, it’s like sitting in this scene and just breathing deeply and relaxing:

If you’re curious, I recommend downloading the app and just trying for a few days.

Negative Habit: Avoiding Alcohol

I tend to drink 1 – 2x a week, and rarely do I feel like I’d be missing much if I stopped. So skipping alcohol for a month seemed like a pretty easy start to the year.

And for the most part, it was easy, but there were definitely a few times towards the end of the month when I really, really wanted a glass of wine. Particularly when eating good food with good friends, I find a glass of wine to easily double or triple my enjoyment of the experience (sorry, friends).

I will NOT be keeping my teetotaling habit going forward :)

New Experience: Cryotherapy

I’d never heard of cryotherapy until Tony Robbins talked about it on the Tim Ferriss Show podcast. Basically, it works like this: you strip down to your underwear, put on some socks and mittens, and then stand in a little booth while nitrogen gas is pumped into the booth. The air temperature drops to between -250 F and -300 F (yes, three hundred freaking degrees below zero) and you stand there freezing to death for three minutes.

Why the hell would anyone subject themselves to this, you might ask? Well, apparently it’s good for inflammation, and you also get a rush of endorphins after it’s over. The people who do it swear by it. Mr Money-Bags Robbins has even had the equipment installed in all his homes.

It seemed interesting, and probably more fun than doing an ice bath, with some of the same benefits, so I figured I’d give it a try. A friend bravely decided to accompany me and we found a place in Manhattan where we could do the procedure.

I’m going to do a separate post about this (with video), but here’s a spoiler:

It was cold. Really, really cold.


So that’s my overview of January. I’m feeling great about the way the year started, and February is off to a good start as well. I’ll write more about it in a post later this week.

I’m on the lookout for ideas for new habits or experiences, so you must share anything you’ve tried that has worked for you!



Why I’m not doing annual goals anymore (hint: it doesn’t work)

Posted in Goals, Habits, Posts by

I used to set annual goals (aka New Year’s Resolutions), but like so many others, I typically didn’t accomplish them. So I do a couple things differently now:

1. Break the year into smaller chunks (quarters and months) and do things around those timeframes

For example, I set quarterly goals for a few different areas of my life, like income, or finish a particular phase of a project, etc. The 12 Week Year and Pick Four are both good resources for this.

I also have started doing habit and one-off goals per month. So for 2015, every month I’m doing a set of one positive habits (do something every day), one negative habit (don’t do something at all), and one new experience.

For example, during January I meditated every day (positive habit), abstained from alcohol (negative habit), and tried out cryotherapy (experience). I’ll write up a separate post tomorrow on the monthly habits and experiences, and an overview of how Jan went and what I’m doing for February.

The only exception I can really think of right now is that I have a goal to read 100 books this year (more on this later). I probably should break that down to 25 books per quarter or 8-9 books per month though.

2. Focus my efforts on habits and systems over goals.

This helps me to focus my energy and attention on what’s actionable today, rather than something months away. I do still set some goals, but mainly as a way to calibrate my habits and systems.

So what’s the best way to figure out realistic goals and habits that fit together?

It depends on the topic, but I use one of two methods for goal-setting and habit formation:

Habit first: I look at the progress I’m making with current habits and the trend I’m currently on, and I extrapolate out from there to figure out what a realistic target goal is.

I’ll also typically add bit to the goal so I have to push myself. So if I’m reading an hour a day as a habit, and the books I typically read take 8 hours to finish, that’s ~3 books per month, depending on whether I do that habit on weekends. So I might set a quarterly goal of 10 or 12 books, instead of the nine that my current habit would predict.

Goal first: I look at where I want to be by a particular timeframe and then figure out what I need to do on a daily basis as a habit to reach that goal.

Which I use really depends on the subject. Sometimes I want to accomplish something by a particular date because of other things going on in my life, and I’d use the goal-first method. Mostly I think it’s a good idea to use the habit-first method, as it’s easier to nudge what you’re already doing into better performance than to overhaul everything all at once to meet some lofty goals. Although some things do require you to go cold turkey, so I guess there isn’t a hard-and-fast rule :)

But regardless of which method I use, I do a sanity-check with the opposite method. So if I’m wanting to read 25 books per quarter and I back that out to be 2 books per week, but my current reading habits have me reading a book every other month, I need to be thoughtful about whether I can shift my habits to the degree required to reach my goal.

Sadly, I’ve gotten out of the habit of keeping written goals, and that’s a terrible shortcoming. I think I focused so much on written goals back when I was setting annual goals that I basically got discouraged and felt that written goals weren’t worth focusing on. But in retrospect, I definitely feel that I should be tracking all my goals and habits in one place. I do track my habits, but I’ll be adding my goals to that list as well.

I’d love to hear from you what goals, systems, habits, etc. have worked (or not worked) for you in the past and what you’re doing these days.



The most common failure mode is failing to show up

Posted in Achievement, Goals, Habits, Posts by

Lately, I’ve been worried about one of my projects and whether it is going to be able to provide enough revenue to be viable. I’ve been worrying that I haven’t yet found the right combination of things to do in order to make it all work. Here’s the thing though: I haven’t tried the combinations I have thought of. This project is failing, but it’s not failing because I’m doing the wrong things. It’s failing because I’m not doing anything.

“Eighty percent of success is showing up.” -Woody Allen

This is something I know, but I forget it constantly. Let me give you a few more examples:

  1. I put off hiring a virtual assistant for forever because I worried that I wouldn’t be able to manage one very well, or that I’d have to put more time into thinking about it than it would save me.
  2. I put off getting back into fitness in a serious way because I worried that I didn’t have the right workout plan.
  3. I put off getting serious about my consulting career because I didn’t think that I’d be able to get the types of gigs that I wanted.
  4. I put off restarting my blogging after taking some time off because I wasn’t sure how it fit into my overall personal brand.
  5. I put off building and selling iOS apps of my own because I wasn’t sure I’d be able to make a decent return on my investment.

These are just a few examples from the past few years. I’ve bit the bullet and done all of the above, and most have worked out far better than I expected:

  1. I recently started using a VA service called FancyHands (affiliate link) and so far it’s been great. I’ve had to put a little thought into what I can pass to them, the best way to do it, etc, but so far it’s been a positive experience.
  2. My fitness always goes in cycles where I do well for a few months then not as well for a couple months, etc. I’m working on that, but my periods where I do well almost always start with me going to the gym for a few days and just screwing around, doing whatever exercises I feel like doing, etc. It’s not efficient or effective in terms of the workout, but it starts the momentum and then I gradually get my routine figured out and I’m off to the races.
  3. I should write several posts on my consulting career, but a couple years ago I started getting serious about it in terms of beefing up my skills, charging more, and focusing on my lead pipeline. The results have been amazing, and I’m grateful to have a host of awesome clients. It’s been a lot of work, but I’m enjoying it like I never have.
  4. Just like with the gym, I tend to go in cycles with my blogging. But my posts are always rough and painful when I start again after a long absence. I have trouble coming up with ideas and the writing just feels like a chore. But after a few weeks, I see blog post ideas everywhere, in many day-to-day conversations and experiences. It’s hard to explain, but the whole thing just starts to flow.
  5. On the iOS apps, it turns out I was right to hesitate. I put out a simple app earlier this year, just a toy really, but after that experience, listening to other people selling apps, and looking at how much I make as an iOS contract developer, I’m pretty sure that I won’t be releasing any more iOS apps of my own. Live and learn.

So not all have worked out (yet), but most have. But none of them worked out right away. They all took me showing up and working at it for awhile.

Get momentum, then refine

Momentum is powerful. Call it habit, whatever, but bottom line: it’s easier to keep moving than to start moving.

The easiest thing you can do today is nothing. The second easiest thing you can is planning to do something later. They’re both about as useful. If anything, planning is more dangerous because it makes you feel like you’re making forward progress, but you’re really not.

Do something. Even if it’s the wrong thing, just do something. It might not be as wrong as you think, and if it is, you can adjust and do better next time.



2012 Prediction: an A-list director will fund a film on Kickstarter

Posted in Entrepreneurship, Inspiration, Posts, Social Media, Technology by

Here’s my prediction: sometime in 2012, an A-list film director will successfully fund a feature film using Kickstarter.

Kickstarter’s time has come. If you haven’t heard of Kickstarter, you’re about to. If you have, you’ll still find this interesting.


Kickstarter was launched in 2008 as a “crowdfunding” site and it works like this:

Someone who wants to create something (like a film, book, physical gadget, or website) creates a fundraising project. Every project has a deadline and a minimum funding amount, like $25,000. And then the project creator creates a number of pledge amount options ($5, $10, $50, $100, etc) and a prize that goes along with each one (like a t-shirt).

People who want to see that thing be created can pledge those different amounts and if the minimum fundraising goal is reached, their credit cards are charged and they get the prize that corresponds to that pledge level. If they don’t hit the minimum by the deadline, no one gets charged anything.

Pretty simple.

What’s odd is that this actually works. Really, really well. Since they launched, something like 50,000 projects have been launched on Kickstarter, and almost half have been successfully funded. And we’re not talking small numbers either; of the 27k projects launched in 2011, the average pledges collected per project was about $3600.

More on the stats here.

And then you have the monster projects, some of which have raised hundreds of thousands. You can see a list of those here.

So clearly Kickstarter is a really cool way for people to get money for their creative projects. But it’s about to become a lot more.

Two very significant milestones for Kickstarter came last week. The first is that one of their projects passed $1mm in pledges. A product designer put together an amazing iPhone dock and basically sold tens of thousands of pre-orders. Pretty unbelieveable.

But the bigger milestone came when veteran game designer Tim Schafer posted a fundraising project for his new game, Double Fine Adventure. He was trying to raise $400k in 35 days or something.

Instead he hit that $400k in about 8 hours. And the pledges just kept rolling in, hitting $1mm in less than 24 hours. As I write this, it’s at $1.77mm with 27 days left to go. More than 50,000 people have backed the project so far. I fully expect the media will pick this up in the next few days and the project will easily pass $2mm and possibly $3mm.

Something crazy is happening here. Kickstarter is obviously an amazing way for people with no following and no reputation to get their ideas funded. But Tim Schafer has just proven that it’s an amazing way for people with a following to get their stuff funded as well.

If I was a top director with an indie project I wanted to get funded, I’d be out right now shooting a trailer so I could post the mother of all Kickstarter projects. Not because I couldn’t get it funded any other way, but because the impact of having 100,000 or 200,000 donors backing your film would be huge.

While we’re waiting for that moment, what could you put on Kickstarter? Do you have an idea for a cool creative project or a gadget to make people’s lives better? Why not post it? What do you have to lose?


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