It can be difficult to know when to stretch your existing team to fill out a project, start a new hiring process in anticipation of work, or simply hire a freelancer to help complete a project team. I’ve worked with companies as a project lead, temporary project manager, and full-time contract project manager, and it’s not always easy to get freelance hiring and fit right.

Make Post-Launch a Success (Presented at Ground Control Conf in London, April 2017)

It’s launch day! You and your team have worked hard to achieve this — the moment when you release your client’s website into the wild, ready to go off and live on its own.

I’ve started a little project management newsletter called DPM(ish)—I’ve been wanting to do it for months, and finally went for it. We’re a few issues in and I’ve been sharing all of my mostly-project management thoughts, links, and news there.

As most of my friends/fam know, I’ve spent the last three or so years moving all over at a somewhat frantic pace (god knows my mail can’t keep up with me!). It was all spurred on after a hasty and messy breakup, moving home to recoup and then moving into my first—and most beautiful—apartment.

Have you ever taken over a project and realized you don’t know where to find the SOW or deliverables at all? What about all those times you’ve picked a project back up after launch to add a feature and had to do your best impression of Sherlock Holmes to dig out what went down on the project before it launched? If you’ve experienced these things, then you’ve experienced project management debt.

I recently wrote about overcoming project management obstacles when jumping into a new project as a freelancer—but what about actually getting going and starting to manage a project when everyone else is already in the middle of it?

As a freelance project manager, I’ve jumped into projects at almost any phase: from projects a few days away from launching or kickoffs right after proposals are accepted, I’ve been a part of it all.

One of the biggest challenges I face as a remote project manager is that of instant gratification in communication. I’m an extroverted people-person and also happen to be a verbal linguistic learner. Solving a problem that requires others’ input works best for me when it’s done on a voice or video call, which isn’t always possible when working remotely.

Contract project management isn’t as common in the tech world as freelance design or development is, and it’s still somewhat of a novelty.

After another year of freelancing, building client relationships, dealing with both great and difficult projects, working with incredibly strong partners, moving halfway across the country, and a whole host of project management/tech events, I’ve really refined my approach to work that I take on.

Mitigating the mental realization that I know much less about the technical details of the development process than I thought I did is difficult at times—and can lead to self-doubt towards my role as a freelance project manager.

This is the first in a monthly series prompted by Sparkbox, to start more meaningful conversations about our web industry. A new topic is announced the first Monday of every month, and on the last Friday of the month, everyone taking part in the monthly topic will post a link to their article with the hashtag #startYourShift. This month’s topic is “How to Make the Web Better”.

I recently wrote a post detailing the process I went through to create a retrospective plan for a non-agile team. Here are the related resources.

A few months ago I was messy-bun-deep into a web project that was consuming all of myself and my team’s time, energy, and resolve. The project was tough for a number of reasons (actually, all of the possible reasons) and led to a lot of emotional highs and lows for everyone involved, as well as a good amount of frustration.

I’ve signed up for a number of premium accounts over the past year for productivity apps and trackers—part of the semi-realistic appeal of an ‘organized self’ that I strive for as a project manager but never quite attain. I thought I’d try to make something of it this year, as well as data from all of the apps I use to track things like my steps, books I’ve read, music, and more.

After many instances of pronouncing my Twitter username and this domain for friends and colleagues, I’ve realized I never included an explanation of this anywhere public.

How did you start contract project managing?

I was looking to leave my job at the time and had been pursuing job leads for a month or two. I received offers at a well-known agency in Boston and a few remote-based positions and realized a few things.

The Search for the Holy Grail: Creating Tools and Processes for Your Team

Originally presented at the Digital PM Summit, Austin, TX October 2014. Share and save the slideshow here.

Over the next few weeks I’d like to document the process I’ve gone through to switch to working for myself full-time, the applications I use to stay organized, what I’m learning as I go, and how I’m managing my schedule. I always love looking back on this stuff for myself, and I have small hopes that some people might be interested in reading this as well! I know I’m always curious about what other people do and what their workflow is.

I’m excited to announce that a few weeks ago, I left my position in marketing at Mohawk in order to pursue a few new opportunities in project management! My main goals and reasoning were to get back into the digital/web project space, which I’ve really missed, and am so excited to continue again full-time.