A Letter to the Overambitious


Hey there,

I've noticed that you haven't been yourself lately. You seem scattered during calls. It’s not always easy to tell through a screen but you appear to be exhausted.

A couple of weeks ago, you mentioned putting in some extra hours on a project and asked for advice with time management. Is it that the projects you're working on are too much or something else? We aligned on the schedules together prior to starting but I know conflicts don’t always present themselves until the project starts moving. It's normal to course-correct as we go.

When we last spoke, we discussed the importance of blocking out your day and owning your calendar. It's easy to point to meetings as a "time suck" and sometimes, that's true. Yes, they can break up the day in a way that feels unproductive but the fact is, meetings aren't going away. We're a team and we lean on each other's expertise to be successful. Ultimately, it's up to each of us to decide how we use our time. We can start by determining where we can add the most value and work with our team to find meeting times that work best for everyone. In the end, we’re all striving towards the same goals.

Part of me wonders if time management is really just a symptom of a bigger, underlying issue. Your ambition for perfection or in other words, desire to do "the best" in everything you work on. Trust me, my younger self can relate. This is a valuable quality to have but without control and a realistic outlook, it can lead to dark places. Literally. The lights are probably off and it's almost midnight. You're still working. Why?

What is "the best" anyway? It is not only subjective but can and should change with every task, client, and project. It is our jobs to align and establish what it means to be successful within the guardrails provided on any new project. These are often driven by timeline and budget but may also include working with a comprehensive brand guideline or existing assets.

We can't forget that we are being hired by a client to make work that will help them achieve a certain outcome. Success is driven by our ability to meet that outcome. Sure, we have our own quality standards. We want to make work that we're proud of. We want to make work that raises the bar. That shouldn't get in the way of enjoying the process of making the work or frankly, delivering that outcome.

Back to the guardrails. I like to think of guardrails as setting the bar on every project. Guardrails should help us paint a picture of what we can accomplish given the constraints. A 3-week brand extension project that leverages an existing style guide is not the same as 6-month branding project starting from scratch. We should approach them with the same energy but we can't expect the path to be the same. It's just not possible. We wouldn't be in business if we treated them that way. This is why the car wash I go to in my hometown has 5 types of washes, starting at $3. I know, wild. I don't pay $3 and expect the best wash they have to offer. I get the best wash they can give me for $3.

We need to use these guardrails to build efficiencies. We need to use these guardrails to determine what path is the right path for achieving our client's desired outcome. This means that the deliverables and milestones can and in some cases, should change. Why wouldn't they if everything else has?

In the words of Jason Fried (37signals/Basecamp) in his book It Doesn't Have to Be Crazy at Work:

"If you can't fit everything you want to do within 40 hours per week, you need to get better at picking what to do, not work longer hours. Most of what we think we have to do, we don't have to do at all. It's a choice, and often it's a poor one."

Simply put, it's painful to provide the outcomes of the $25 car wash for $3. No kidding. The $25 car wash isn't just throwing extra soap and water at the car, either. It's leveraging different technologies and resources and providing additional services.

It's not uncommon to confuse efficiency for being fast. Speed is about skills expertise. Efficiency is about working smart. They're not one and the same. You can be a speedy worker but spend too much time on all the wrong things. You can also be super efficient but slow when using a specific tool.

At the end of the day, clients will remember how effective we were at delivering the results they hired us for. If we’re able to deliver some added value along the way, that's even better but it's not a requirement, especially if it means losing sleep or ultimately, burning out. Even with the best intentions, when we try to do the $25 car wash for $3, we risk not even washing the car. If we miss the client's deadline or fail to meet their objective, they don't remember our good intentions.

I want you to make work your proud of and feel good doing it. No matter what the project is. For starters, I hope this has been helpful in shedding some light on how to navigate the many shapes and sizes of projects we'll inevitably work on in the coming months. I have no doubt you can thrive within any project's guardrails but we can't expect everything to change tomorrow either.

Starting tomorrow, let's connect weekly. We can talk through your plan for current projects, how you're spending your time, and reflect on past experiences. If, for any reason, we agree that additional work is worth the added value, we'll align on what it will take to get there.

In the meantime, please give these questions some thought:

  • If you had no choice but to end your work when the work day ended, what would you prioritize?
  • Have you documented the steps for getting your work done? If not, how do you know when your off track?
  • Have you defined success for everything you're working on? Is your version the same as the client's?
  • At every step, are you using the available time to get actionable client feedback that will narrow options and propel us closer to the solution?
  • Where are we spending too much time without client buy-in?
  • Where are we prioritizing what we care about over what the client is asking us for?

I'm looking forward to reviewing more tomorrow. Until then, take the night off and give yourself some time to rejuvenate.

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