How do you decide when an apprenticeship is complete? When is it time to move on? To call it done?

Do you move on after a certain time period — say two years or so? After you’ve learned “enough”? Or maybe when you get that gut feeling that it’s time to go?

If you’re looking at an exact answer, I’d say “it depends”. However, if you forced me to give broad reaching advice, I’d say 2 years plus however much time you need to accomplish the following:

  • Reach whatever personal goals you have set for yourself
  • Gain the particular skills you know you’ll need for your next project

For a little background, I spent my apprenticeship at a graphic design company who offered their services in a “productized” model. In the time that I was there, we grew from a small team of 10 or so to 25-ish employees on the US side, and from 100 or so designers to over 250 designers on the Phillippines side.

The goal for my apprenticeship was to understand how a small(ish) internet based business is run, what the big challenges are, how one may tackle them, and get some reps in on the company dime and time on how to run a product and a business. I promised myself I’d take in every bit of learning I could, give my all to the role, take ownership wherever possible, and see what I could accomplish.

During my time there, I learned the guts of how something I’d like to run could be run, from marketing and sales to product, customer service, and development. And then some.

I also had two particularly helpful experiences. The first experience was running a software product that was a side project for the company. I learned what running a small SaaS would really be like. Second, I led a small product team that was able to ship some really cool stuff. I’m really proud of the work we did there and was fortunate to work with a really great group of people.

2.4 years in I knew it was time to go.

Even with all the great experiences I was having, I was starting to bump up against some barriers. I started to realize that I may be best suited for earlier stage work and that the detailed, process-oriented work that is required to take a company beyond ten million may not be my forte and was not enjoyable work for me. That was turning into the majority of my work. Also, while I loved managing, I missed creating.

If I stayed longer, I could learn how to lead larger teams. That’s cool and all — but my long-term goal is not to build some massive business with hundreds of employees. It’s to build a small team that builds a meaningful product that customers love. Keyword small.

I also put my whole energy into the role. My team was spread out literally across the globe, from eastern Europe to Asia, there was almost always someone on my team online at every hour of the day. That meant a lot of slack messages at odd hours. I felt like I needed to be there for everyone all the time, and that started to take a toll of my mental health. A sense of burnout started to creep in. I was tired.

It was indeed time.

When the day came around and I put in my notice, I felt guilty. I felt guilty for leaving my team. I felt guilty for leaving such a great position (that was a great product role, and it was remote to boot). I felt guilty for wanting to be selfish and pursue my own goals.

I cried when I put in my resignation, but I knew it was the right decision. After getting all the leaving bits in order, I breathed a sigh of relief knowing I now had some time to re-focus on the next step of making my long-term goals come true.

Recovery Phase

Creative juice level - 30%

Right after leaving, I had a few options of what to do next, from doing some consulting work, to taking some ownership of the company side project mentioned above, to joining a role my friend recommended me for at a growing company.

But I needed a break. My creative juice levels were at all time lows. I’d sit in front of my journal and nothing would come out of my brain. That’s a real bad sign for me. Usually I could fill up pages with random ideas, plans, and thoughts. But now, nothing.

So, how could I get my creative groove back?

My first order of business was running the marathon I’d been training for. So I did that. It was cold, wet, and miserable, but I did it! It turns out committing to a plan no matter how much it sucks can help you get where you want to be. The marathon also happened to be near the Willamette valley, so after that we visited some friends, hung out with a whole bunch of cute golden retrievers, and drank more than a couple of bottles of pinot.

I’m grateful that I had some activities planned after leaving. It made the transition to not having a “real” plan yet that much easier.

After the marathon and travel were over and I was back in Austin, I still woke up every day thinking about my last role for a week or so. Old habits die hard. But let’s not lie now, I did bask in the lack of Slack notifications. Those first couple of weeks I spent just cleaning, working out, writing in my notebook, napping, meditating, and painting. Unstructured time felt great, if not a bit anxiety provoking at times for someone who is usually very goal oriented.

Then it was off to Portugal for a month to hang out, relax, and re-find myself Eat, Love, Pray style.

Just kidding!

My loose goal for the trip was to learn some new things and explore Lisbon, not try to cram years of self-discovery into one month.

Directionless Exploration

During the Portugal trip and the months that proceeded it, I decided it’d be fun to explore some things I was interested in since I now had some time on my hands. You know, making progress on the “I should do that one day” type things.

First up was programming. I decided to learn Ruby, JavaScript, and dive back into Ruby on Rails. Tailwind CSS was also something I wanted to explore.

Also on the list was finally reading some classic literature, learning a new language, cooking more, redoing my personal site, decluttering, completing some projects around the house, signing up for an ultramarathon, and more.

I figured I’d start tackling some of the ideas on the list and not fully commit to any one thing in particular. I’d pursue the things that piqued my curiousity. What I actually got around to doing was less than my (lofty) aspirations. I still managed to accomplish quite a bit and dabble in a few topic areas like:

  • Ruby, RoR
  • JavaScript, Vue
  • TailwindCSS
  • Spending time outside
  • Signing up/training for an ultra
  • Turning this site into a static site (on gatsby)
  • Reading Candide, The Brothers Karamazov, 100 Years of Solitude
  • Drinking lots of espresso and Portugese wine
  • Picking up an enjoyment of tinned sardines on toast
  • Reflecting on past year and go through previous years annual reflections

At this time, I’d spent November in Portugal and December/Beginning of January at home with family. I love my family, but I was starting to get that itch to get out of there and do something productive. My creative batteries were recharged and I was ready to get stuff done.

Latching On

Now that I was recharged and had all this potential creative energy, the next question was…what should I direct it to?

I’m a big fan of project based learning. You can only learn so much from reading about something. Plus, having a project I feel is a great way to feel accomplished as you move something from an idea into something that’s tangible.

However, I’m not a fan of coming up with a solution first and then trying to find the problem it solves. That’s silly. I’d rather start with a growing market and then figure out what problems they’re having and solve those. I feel like the most “duh” way of doing this is identifying which markets you’re a part of, making a list of the problems you deal with on a daily basis, and tackling one of those.

I consider myself a member of the product manager community and most strongly identify with that group professionally. Some of the problems I had were:

  • Not writing good enough specs
  • Having to constantly prioritize and say no
  • Lacking coordination and know-how to do good product marketing
  • Balancing market, customer, and stakeholder needs
  • Managing roadmaps and schedules
  • Fielding questions and requests from what felt like everyone
  • Managing knowledge bases
  • Staying ahead of communication

I pursued “building better specs” for a while and then moved on to better prioritization. Mostly because “spec management” as a category doesn’t really exist yet and I didn’t want to try to break into something new as a bootstrapper.

However, there were some companies out there already doing project and product prioritization, so I realized that’d probably be better to go into since I wouldn’t have to spend all that energy explaining what it is that I’m making.

Now, should build it myself or outsource it? Since I knew the basics of programming and product management, I could probably outsource it without getting swindled. However, right now I have more time than money, so I decided to go the route of building it myself.

While I’m trying to metaphorically burn the bridges and go all in on this entrepreneurship thing, I know that knowing how to develop a web app is a good skill to have should ever SHTF and I need to get a job for a while.

This next part of the story is the boring part. It’s the part where I wake up every morning, get in my morning coffee, meditation, journal, run, and fire up my text editor. Then proceed to “program”.

What I really do is a combination of banging my head against the wall, silently mouthing “wtf why won’t this work?”, googling things, trying small tweaks and refreshing, and writing a bit of code. I’ve been getting more efficient at this as time has gone on.

I now find myself writing my own code, which sounds stupid, but I feel like is an indicator of how far I’ve come in just the past couple of months. No more copying and pasting from StackOverflow.

Some days I make a lot of progress, and some days I feel like I’ve made negative progress. However, I’ve never felt more fulfilled, relaxed, and happy — even though some days just absolutely suck.

I also got myself a codementor, who has been an indespensable help for when I get stuck. There are just some programming things that you seem to have to learn from other programmers. My GoRails membership has also proven to be an amazing way to learn how to build real, useful features into my application.

Current Project

So what’s next? Well that spec management tool I mentioned before evolved into a product prioritization tool. It’s stupid simple. Embarassingly so I’m afraid.

As a product manager, you can add all of your potential product ideas, features, bugs, improvements, stakeholder requests, and whatever else is on that long list of yours and prioritize it in a way that makes sense for your goals.

Want to make sure you’re building things the customer wants? You can evaluate all your ideas on customer demand. Maybe you’re more concerned about keeping your crazy boss happy. Then prioritize for that. Or perhaps in this crazy time, you want to make sure everything new can generate a buck and keep long-term customers. Then prioritize for those criteria.

As a PM, it’s really easy to build the wrong things. It’s friggin hard to build the right things at the right time. That’s what Speckled is for. Making better product decisions.

I have a rough landing page up right now at GetSpeckled.com. It’s not exactly sign-up-able yet, but it’s getting there slowly but surely. Over the next couple of weeks I’ll be getting to the point where I feel more comfortable demo-ing it.

So that’s what’s next! Could it have come with better timing in the midst of all this Covid-19 stuff? Sure! But it is what it is.

Alright, back to coding!