2018 Year In Review: Unhealthy

I’ve tried and failed to write annual review posts before. Part of the issue has been that it seems so big and overwhelming, so I’m going to try and make it easy by using a short template that I fill out. Hopefully that’ll make it easier to stick with going forward.

Two things to keep in mind as you read this:

  1. This is primarily for me. It’s obviously not entirely for me, as I’m publishing it, but I don’t know that anyone will really be all that interested in these things. So if you’re wondering why I’m blathering on about myself for four thousand words, just close this tab and move on.
  2. I’ve decided to be brutally honest about everything in this annual review. Partly because I’m not sure if anyone will read it, but also because I’m getting too old and tired to care too much what people think. I still do, but I shouldn’t. So if you’re offended or concerned or whatever, you’re welcome to drop me a line and open a polite dialog. Or if polite is out of reach, you can just close the tab and keep your thoughts to yourself.

What were your high-point and low-point for 2018?

High point: moving back to NYC

We moved to Nashville in 2015 and we just moved back to NYC at the start of 2018. We really enjoyed our time in Nashville, but it ultimately just wasn’t for us. I couldn’t be happier to be back in NYC, and I don’t expect to move again. You can read more about our adventures in Nashville here.

Low point: moment of truth for my business

This came just recently, and was definitely a “dark night of the soul” for me. But I’m feeling much better about it. More about this later in this post.

What did you change your mind about?

Drugs. You can read more about it here, but the short version is that I’ve tried cannabis a few times and am fully convinced that it’s no big deal for the vast majority of people. Now I’d like to explore psychedelics like psilocybin mushrooms, Ayahuasca, or perhaps LSD, but only in a guided and carefully controlled setting.

I know, that sounds crazy, but please let me explain. I am a (comparatively) responsible and thoughtful adult, and I don’t take any of this lightly.

I got to this point as a consequence of two separate trends:

  1. Realizing that I’ve been lied to my entire life with a message that “all drugs are terrible and will destroy your life!”, when the reality is much more nuanced. All drugs are not the same, and after trying marijuana a few times over the last couple years, I don’t trust the anti-drug crowd at all.
  2. Hearing many people that I follow and respect talk openly about their experiences with these compounds. Major examples include Tim Ferriss and Sam Harris, and I really enjoyed the recent book How to Change Your Mind by Michael Pollan.

The bottom line for me is that I want to better understand my mind, break out of some thought patterns I’ve developed, and understand what it means to be less ego-centric.

And I’m talking about it openly because there’s a stigma around this topic that I think is wholly unreasonable. I’m not the world’s most successful person, but I’m hardly the stereotypical lazy pothead.

Disclaimer: this is NOT legal or medical advice. All drugs (even the most mild ones like caffeine or marijuana) have the potential for physical, psychological, and/or legal harm, and you should make your own careful decisions about whether to consume them, and be cautious about the dose and setting if you do so. If you’re unsure, seek the advice of your doctor, attorney, and priest.

What did you succeed at?

I suffer from something I call the delegation yoyo. Basically, it’s where I avoid hiring someone to help with things until I’m so overwhelmed and burned out that I over-hire and try and get the person to do TOO much without even training them. Then a few months later I end up freaking out about how much I’m paying and going back to doing everything myself so I can “save money”. Rinse and repeat.

So, so stupid.

I know, this is quite a way to start off the “what did I succeed at” answer, isn’t it?

In 2018, I finally decided that this is an area that I need to master. I’ve been running my own solo business for over a decade, and I’ve never really learned how to effectively delegate, outsource, and manage people for the long run.

So in May I hired two people and put together training materials for 70% of what we’re doing together so they know what they’re supposed to be doing.

(Pro-tip: default to doing training as a screencast. Makes it SO much easier than trying to write it all out, which means you’ll actually do it. And if you want it written out, have someone like your VA do that based on the screencast!)

I hired Danielle to be my part-time virtual assistant, via an excellent service called Worldwide101. It’s not cheap, but you get what you pay for, and Danielle has been awesome to work with.

I also hired Justin to run the daily lead curation operations for Everleads, where we help designers and developers find freelance work. He’s been doing an amazing job, and it’s so nice to have this off my plate again.

Overall, having help has been amazing, but I still didn’t get it quite right. In particular I still over-hired a bit for my VA.

I should have hired a bit under the capacity that I needed and then tried to be efficient or wait until I absolutely needed to scale up before doing so.

Instead I hired a little over the capacity that I needed and then assumed I’d come up with stuff for her to do. Which I kind of did, but that often took the form of me once again throwing poorly defined tasks over the fence without any accompanying training or SOPs.

So for 2019, I’ve scaled back my VA a bit, and I’m going to renew my focus on defining systems with specific training materials (I’m reading and loving the book Clockwork for this).

Not only does it make life easier for both of us to have things clearly defined, it also means that I can easily bring on someone else in the future if needed. Developing those processes and the training materials to let someone walk through them is what it means to work on your business instead of just in your business.

So, not perfect, but overall it’s been a success. I’m determined to figure this out in the long run, to build these systems and processes, so that I can continue to free up my time to focus on the key things that I should be focused on.

What did you fail at?

I failed at growing my product business and watching the bottom line. So yeah, basically the most important parts of a business.

Just a bit of context here: since 2007 I’ve been a full-time freelancer / consultant. Over the last two years I’ve created two product businesses on the side that have taken up more and more of my time. The first is Everleads, which helps designers and developers find freelance clients, and the other is IndieHive, where I sell coaching and some courses for freelancers who want to build stronger businesses.

Revenue for the product businesses was basically flat from 2017 to 2018. I did some client work in 2018, but not enough given that I’m not making enough from Everleads and IndieHive. Despite that, I scaled way back on client work in the fall of 2017 to focus on them. After 15 months I need to face reality: as much as I want to fully focus on my growing audience of freelancers and the products and services I sell them, I’m not there yet. I’m just not making enough to justify that.

Worse, I’ve been living as if that’s not the case for a year now, spending too much on expenses and not doing much consulting work. Basically living as if my product revenue is 3x – 5x what it is. The result is predictable: I’ve run up a ton of debt. Like, a crazy embarrassing amount of debt.

I almost fully recognized this truth a couple times this year, but I didn’t fully face it until the last few weeks, thanks to reading Profit First, which I highly recommend to any entrepreneur.

It’s really stupid, because I have always been able to make great money from consulting, and both Everleads and IndieHive are profitable. There’s a sustainable path here, but I took my eye off the bottom line and wandered off that path. The good news is that with little bit of belt-tightening and focus, I believe 2019 can get us fully back on track.

It’ll be interesting to review this sentiment when I’m writing my 2019 year in review post next January!

Favorite things you created?

  1. Mastermind group – At the start of the year, I put together a mastermind group of myself and four other business owners. We try to meet every 2 weeks, and it’s been really, really helpful for me. So in terms of creation, I didn’t really do anything here other than send some emails, but I’m really glad that I did!
  2. Brand & website – I overhauled my “brand” and website to be more in line with the current business. It’s not perfect but better than what I had, and good enough to carry me through the next chapter.
  3. Staff training systems – Some processes for delegating things, which I discussed above.

Ugh, the shortness of this list is frustrating to me. Very, very frustrating. How can this possibly be all that I created in an entire year??

There are a few other little things, but they’re honestly not worth mentioning.

Favorite things you consumed?

I read a total of about 25 books this year. That’s way, way fewer than I wanted. Most of that is due to my ongoing crippling addiction to political podcasts. I’m working on it!

In no particular order:

Favorite podcasts:

Favorite non-fiction books:

Favorite fiction

Favorite TV shows:

Favorite travel destinations?

I travel a fair amount, and this year had some fun trips:

First, I took three great cruises by myself, which are always a fun way for me to unwind. Did some diving, but mostly just relaxed and spent time reflecting. I’m writing this post on one of those cruises.

I also spent a week in Seattle and Portland with friends, which is always one of the highlights of my year. (This may or may not have been where I had several of my cannabis experiences.)

I traveled to Boise for the first time for Craft+Commerce, which was definitely the best conference I’ve ever been to. Can’t wait to go back in 2019.

I traveled to Las Vegas for MicroConf, which I really enjoyed. I hadn’t been to Vegas in years, but I love it for its unabashed over-the-top gaudiness.

Alexis and I went to Bogota, Colombia for about a week, which was really fun. It’s a great city with an outstanding food scene that’s surprisingly affordable.

Finally, we visited family in California and Colorado, which is always a fun time.

I generally spend 8-12 weeks per year away from home, and I actually really like it that way. My only regret is that I didn’t get to spend more time traveling internationally.

How is your physical health?

Mixed. I’m in fairly good shape, self-assessed anyway.

But the reality is that I’m just treading water, at best. I didn’t improve my health this year the way I wanted. I wanted to spend more time in the gym, but I never found a good situation in NYC to make that happen. That’s partly an excuse, but not entirely.

I did manage to lose a little weight over the last couple months, which has been encouraging. I’m still in a healthy range for weight, but I’d like to build more muscle and lose even more body fat.

But the biggest thing I need to work on is mobility. I rarely stretch or do mobility work, and I recently injured my knee by ramping up my running too fast without warmups, stretching, or cross-training. I probably won’t be running for a couple months as a result. I also had a recent issue with a muscle spasm in my upper back, which is not the first time this has happened.

I think yoga may be in my future in 2019.

How is your mental health?

Much harder to assess, since all I have to assess my mind is…my mind.

Overall, it’s been a stressful and anxiety-inducing year. 90% of that is financial, which is infuriating to me. It feels like a big step backwards from where I was a couple years ago.

More broadly, I’ve spent too much time this year worrying about whether I’m heading in the right direction in my life, etc. I derive an unhealthy amount of my identity from my business and work, and so when they’re “failing”, it’s painful and destabilizing for me.

I haven’t invested in relationships like I wanted to this year, both in terms of connecting with old friends and seeking out new ones.

I’ve also become convinced that I need to explore meditation again. I tried several years ago to meditate daily for a month or two, but gave it up when I couldn’t identify any particular benefit. I still do it occasionally when I feel particularly overwhelmed or stressed.

However, I’ve become intrigued at the prospect of using meditation to capture some of the benefits of hallucinogenic drugs without the downsides. In particular, to become less attached to particular outcomes in my personal and business life, and to become less emotionally reactive when things don’t go my way.

Overall, how satisfied are you with 2018, on a scale of 1-10?

I’d give 2018 a “3”. And that’s frustrating as hell to me, because most of that comes down to money. The business didn’t grow like I wanted it to, and it’s been slowly destroying my sanity for the last 18 months.

If the business had exploded in 2018, I’d probably rate this year an “8” or “9”. And it’s frustrating that money and business have such an outsized impact on my life, but I’m not entirely sure of the best way to remedy that. For better or worse, I need to make money and I’m committed to growing this business because I think it’s a better fit for me in the long run than the other paths available to me. So it may be that some of the stress that accompanies building this business is just a necessary evil.

As one of my least favorite children’s books says: “We can’t go over it, we can’t go under it, we have to go through it.”

That said, as I mentioned before, I do want to explore meditation as a way of being less reactive, less tethered to my expectations and the inevitable shortfall between them and reality. I’ve started using the Waking Up app and that’s going well.

What are you most grateful for over the last year?

  1. Alexis and Junia, obviously
  2. My health, which can be improved, but is still excellent
  3. Danielle and Justin and their impact on the business
  4. The mastermind group and all their support and ideas
  5. Living in NYC

What are you hoping to get out of 2019?

I didn’t have a clear idea of the answer to this question when I started writing this post. But after writing this, I think a clear theme has emerged:

I need to stop chasing huge growth in different areas of my life and instead focus on solid, long-term, sustainable health.

I don’t want to level up. I want to settle down into a healthy sustainable routine that I can do for the next 50 years.

I want healthy endorphins that I look forward to, not yucky vitamins that I choke down because they’re good for me. And that applies to multiple areas of my life:

Healthy body

Yes, I’d like to lose a little weight, gain a little muscle, work out more, get more limber, etc. But the more important thing to me is that these numbers start trending in the right direction, instead of the long slow decline they’ve been on over the past decade. So my focus is going to be on inputs, ensuring that I’m working out regularly, doing yoga a couple times a week, stretching a couple times per day, being thoughtful about what I eat, and protecting the quantity and quality of my sleep. If I do this every day, the outcomes I want will come.

Healthy mind

In addition to exploring psilocybin in a guided setting, I want to integrate meditation into my daily practice. I also want to read more and consume less of all other forms of media. And I want to spend more time creating and doing deep work, instead of mindlessly consuming, using devices out of boredom or inertia, and getting caught in shallow tasks.

Healthy business

I want to keep my businesses profitable and growing, but I’m getting over the desire I had to “10x” the business in a few months or whatever. I want them to be profitable enough to make a comfortable living and growing enough that it remains interesting and challenging. But more importantly, I want to deeply enjoy what I’m doing every day, to feel engaged and challenged, and hopeful about the future, not fearful about what might happen if I don’t find the magic key to unlock exponential growth. If I can do that, what difference does it make whether it takes two years or two decades to double the business?

Ego and impatience got me into this mess, and it feels good to let go of them at least a little bit.

Healthy relationships

This is a tricky one, because I have zero idea how to quantify it, or even if I should attempt to do so.

I know I’m not alone in hungering for real social connection: loneliness is a huge and growing problem in our society. And I’m very fortunate to have family and an large group of friends, but I want to do two things to improve:

First, I want to spend more time with family, like my wife, daughter, parents, siblings, etc. And I want that time to be more intentional and meaningful. Less taken for granted.

I also want to start fostering the kinds of community that I want to be a part of. I spent more than three decades of my life in the church, and the best thing about it by far is the relationships that religious contexts offer.

Since leaving the church, I haven’t found another community that offers the same shared set of values, propensity to gather regularly, etc. Being self-employed makes this even worse, because no real work friends.

But what I’ve finally figured out is that a lot of other people want this to, and we all suck at creating it. People are generally bad at creating and nurturing meaningful relationships in the modern context.

And while I expect it’ll take years to make much of a dent, I want to start learning how to do that. How do you foster a genuine sense of shared community where people feel welcome, known, and valued?

This post is actually part of that, because I think honesty and vulnerability is a good place to start. So if you read this and anything resonates, email me. And let’s grab lunch or a movie or a workout or whatever if you’re in NYC (or I’m going to be in your city).

Healthy habits

Momentum is so powerful. And nothing creates it for me like daily habits. It’s always been that way. Nothing else has enabled as much long-term sticky behavioral change.

For the last few months, I’ve been implementing a set of five core habits that help me accomplish all of the above, and also create the time and energy to do other positive things.

Saying you want to weigh a certain amount is nice, but kind of useless. You have to translate that into the specific, repeated actions that you’ll take to get there. These habits are the ruthless, relentless engine that drive me forward to the goals and outcomes that I want.

I started with Tim Ferriss’s question about behavior change: “what would it look like if this were easy?”

For me, this question is a great way to start habits, but it’s not enough to stay there, just doing the bare minimum. So I came up with the tiniest, easiest version of these habits I could live with and ramped up slowly every week as I integrated them into my life. After almost three months, I’ve almost to where I want to stay with these habits:

  1. Exercise for 60 mins
  2. Read for 90 mins
  3. Write for 90 mins
  4. 4 hours of deep work
  5. All devices off at 830p

The hardest of these to hit consistently is the 4 hours of deep work. It requires careful planning and attention to scheduling to ensure that you can always set aside that much time to work on deep work. I still cheat by allowing myself to split it up into two chunks of at least 1 hour each. But I’m working towards dropping that so I can do it all at once.

The most important of these is the last one: devices off at 830p. If I turn off all my devices, it’s very unlikely that I’ll stay up too late doing mindless bullshit. Which means I’ll get to bed at a good time, get plenty of sleep, and get up early. I’m a natural night owl, but I’m currently getting up at 430am, which means that I have ample time to get ahead of the day and ensure that the other habits (and other positive things I want to spend my time and attention on) pose no problem for me.

I do these habits Monday through Friday and I take time off for holidays, vacation, sickness, etc. But as little as possible, because otherwise it’s hard to regain the momentum!

I’ve also started using the SELF Journal, which is a good fit for me and the way I do habits, goals, planning, etc. There are a number of these types of structured journals, but I got this one at a conference and it’s useful for now.


This is over 4000 words now, and has spawned numerous other posts in the process. I didn’t publish anything at all in 2018, so I suppose I just had a lot pent up.

Since this is my year in review post and I don’t mind being a little cheesy, I want to close by quoting something Carl Sagan wrote about the Pale Blue Dot, a picture of earth taken from 6 billion kilometers by Voyager 1:

We succeeded in taking that picture from deep space, and, if you look at it, you see a dot. That’s here. That’s home. That’s us. On it, everyone you ever heard of, every human being who ever lived, lived out their lives. The aggregate of all our joys and sufferings, thousands of confident religions, ideologies and economic doctrines, every hunter and forager, every hero and coward, every creator and destroyer of civilizations, every king and peasant, every young couple in love, every hopeful child, every mother and father, every inventor and explorer, every teacher of morals, every corrupt politician, every superstar, every supreme leader, every saint and sinner in the history of our species, lived there on a mote of dust, suspended in a sunbeam.

No, I didn’t have a great year.

No, I’m not thrilled about the current state my country is in, let alone the future of the planet.

Yes, the world is full of problems, of suffering, of death and misery.

In spite of that, at this moment I’m filled with more hope and gratitude than I can ever remember. Because life is somehow also full of unimaginable beauty, creativity, elegance, and grace.

It has always been this way, this mix of good and bad, because that’s where life exists, that’s what makes this whole thing worth doing.

So I couldn’t be more excited and grateful to be here, in 2019, alive and aware enough to share it with you all.

Now let’s all go have an amazing, hopeful, awe-inspiring 2019!