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Three Short Lessons for the Last Year of My Twenties

I turned 29 last month. No contest or giveaway this year, like the last few birthdays. This year we’ll keep it simple. Three simple lessons I’ve learned as I round the last lap of my twenties.

Just because it isn’t on your resume doesn’t mean it’s not real work. This includes relationships, moving cities, calling customer service, organizing around the house, and taking care of parents. It’s easy to just gloss over these things as chores and distractions if you’re an ambitious person but this is the real meat of life.

You can have it, but only if you want it really badly. There are too many books to read, cities to visit, people to meet, fields to explore, projects to start. You can’t have it all, but if something is really important to you, you’ll find a way to get it.

Energy is everything. I mean both physical and mental energy (the two are closely related). Avoid things that unnecessarily drain you and move towards the things that fill you up. If you’re well-rested, well-fed, physical active, doing meaningful work, you’re doing great. Also surrounded by people you love, and who love you? Game over. You win.

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12 Enterprise SaaS Startup Lessons Learned in 120 Days at Percolate

Four months ago, I joined the marketing team at Percolate, a marketing technology platform. We work with brands like GE, Mastercard, Unilever to help them plan, create, publish, and analyze their marketing content — with a big vision to transform marketing through technology.

It’s been a blast. I’m responsible for the company blog and lead many of our content marketing efforts (whitepapers, case studies, video, etc). I love my team (we’re hiring) and there’s a lot of great momentum at the company.

Having worked primarily in consumer or SMB software companies in sub-10 person teams in SF, I’ve already seen a lot of differences in how a successful post-Series B enterprise software company based in NYC operates. Just like I did when I moved from SF to DC, I’ve tried to capture some useful ideas here (some big, some small) that might be interesting to you as well.

1. Adopting / switching software is a major decision at bigger companies.

It can affect the workflow of dozens, hundreds, potentially thousands of people in various departments and even external organizations. There might even be changes in power dynamics (ex: maybe with the previous software, finance had total visibility but now they need to wait for a report to get exported by the head of marketing). Making the wrong choice could really screw things up and hurt your career — that’s why people often go with the “safer” big corporate option like Oracle or Adobe or Microsoft. Continue reading…

Looking Down at Machu Picchu

Owning Your Decisions

I recently spent 12 days in Peru traveling solo.

It seems like multi-month international trips has become something of a rite of passage for our generation, but I’ve never found a good time to fit it into my schedule. 12 days was the longest I’ve traveled outside of family trips to China with my parents, and my first time traveling alone.

I wasn’t that familiar with the country, had only a basic grasp of Spanish, and a fairly light list of things to do and see. Rather than traveling because I had always wanted to go to Peru, I went because I thought it’d be a good opportunity for personal growth. Continue reading…

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17 Essential Best Practices for Making Things Happen

Note: If you enjoyed this post, I share more strategies for achieving significant growth in mindset, health+fitness, and quality of work in my free newsletter.

After reading through Sarah’s little rules of working life, which I thought was pretty useful stuff, I decided to think through some of my own rules, or as I’m calling them, “Best Practices for Making Things Happen”.

The idea is that these are all maxims that I live and work by, that I’ve learned over time and that I believe have made me more effective in accomplishing meaningful things.

The list is neither complete nor fully elucidated, but that’s totally in line with BP #2 and #7. =)

Would love to hear what you think: questions, feedback, etc.

Jason’s 17 Essential Best Practices for Making Things Happen

  1. Keep the promises you make to yourself. I learned this one from Stephen Covey – we make little promises to ourselves all the time (“I’m going to stop working on weekends.” or “I’ll definitely get a workout in tonight.”) These promises are in fact more important to keep than the ones you make to your customers, your boss or your family. Because private victories come before public ones.
  2. If you’ve got a good idea, try to take some kind of action on it right away. Too often good ideas slip away, either due to momentum (it was exciting at the moment, but less so now) or just through forgetfulness. So when you have a good idea, send an email to a potential collaborator, sketch out some designs, or at the very least, make an Evernote note for the idea. Continue reading…

Sarah Allen’s Little Rules For Working Life

SONY DSCI’ve learned a lot of stuff working with the fellows in my program, particularly Sarah Allen, who’s paired with me on the Smithsonian Transcription Center. I noticed that she’d often mention a policy she had on doing (or not doing) certain things. I remarked that there seemed to be a lot of them and has she ever put them in one place?

Well luckily for us she has. Here are some my favorite policies of Sarah Allen, an incredibly accomplished software developer, manager, and entrepreneur, and my comment on it.

I never take a job where I don’t know at least one team member very well. The most important indicator of success for any group is the quality of the people. VCs invest in the team, rather than the idea, since it is easier for a great team to change their idea, but impossible for a great idea to find a new team. Where you choose to work is an investment.

Most people would say it’s good to get along with your future coworkers when evaluating new jobs, but this policy takes it a lot farther. It essentially means companies where you’re applying cold, or who are pursuing you with no prior connection, is completely off limits. I think you need to be at a certain stage in your career to be able to pull this off, but that time frame is probably sooner than you think (5 years?)

Write stuff down. I take meeting notes and send them out afterwards. I don’t work without a contract. It’s not an issue of trust. There are a thousand small decisions about the work that go unsaid in a meeting. This applies to any collaborative work. Anytime I need to say to you “I will do this” or “I expect you to do that,” a follow-up email will solidify alignment or catch misunderstandings — saving time and forging stronger relationships.

Sarah and I have become known as the note taking fellows. We have a Google Doc pulled up for almost every meeting we’ve been in. A rough count of our Google Drive has around ~170 meeting notes, planning docs, spreadsheets and talking points in just three months.

Iterate. Celebrate. Iterate. Celebrate. I wish I knew where I read this. Celebrate the little things. You can’t really control the big win. It’s the small series of little wins that we can make happen. We need to celebrate these.

One thing I wish we did more at Ridejoy was celebrate the small wins. There was a feeling from some of my other cofounders that we should only celebrate when we hit a really big milestone, but it often felt too far away, and then the celebration was a huge endeavor in itself, which was not ideal. I like this policy.

Tell someone’s boss, in writing, when they do a great job, especially if they are far away in an organization.

This is like a karma thing – we all hope that if other people work with us and find it an awesome experience, that they’d tell our boss (if we had one) how awesome we were doing.

The #1 job of a good manager is hiring and retaining great people. When I’m in a management role and things get crazy, as they often do, I tell this to myself every morning and twice during the day. It takes discipline to spend time writing an excellent job description or having individual meetings with staff when there are urgent, pressing, seemingly more important issues to deal with.

This is exactly the difference between individual contributors and leaders of teams. Your effort as a manager is multiplied when you find the right people, invest in them, and prune when necessary.

Never hire until you’ve interviewed at least three great candidates. Hiring should be a tough decision. We should have to ask ourselves what is really important so we can decide between these amazing people. We should have cause to wonder if we should stretch our budget to hire more than one.

This is such a great rule for preventing a “He/She is the the one” situations where you fall in love with a candidate. I’ll admit that at Ridejoy, we definitely hired someone we fell in love with, but I think Sarah’s policy is the right one. If you can’t do this, you aren’t recruiting hard enough.

Read them all at: little rules for working life.