A day in the life of an entrepreneur is wildly different from one day to the next. This lack of structure is both a blessing and a curse. It’s why many of us chose this path, and why, at times, it drives us completely insane.
Of course, some people thrive amid the chaos, but most of us need at least some kind of regular schedule to guide us on a day-to-day basis. And when you are your own boss, it’s up to you to create the systems that will provide that structure. Without them, it’s hard not to drift through the days, getting stuff done but only vaguely moving toward our goals.
The key is to take a step back, look at the bigger picture, and connect the dots all the way down to your daily to-do lists. In a fully built-out startup, there’s a person who chiefly owns this role—the product manager.
I recently came across a great description of the part a product manager plays in a company:
Product managers don’t just go to their teams and say, “build me a product.” They have a vision, and they break it down into a strategy, measurable goals, projects, and tasks for their teams.
To break it down a little further, the product manager is the person responsible for overseeing a product from ideation through development and launch. They are the navigator of the ship, balancing the business, finance, technical, design, marketing, and customer needs while working toward their ultimate vision. They work backwards from the top, down to every detail of the vision, and piece by piece, the product gets built. The product manager oversees this process from end-to-end, connecting the dots from the vision all the way to the finish line.
Sign me up, right? Well, if you’re a solopreneur, or otherwise just getting started, chances are you don’t have the budget for such a dedicated team member.
That said, if you are able to look at your work from this perspective—and be your own product manager—the way forward opens up.
This kind of thinking is helpful when faced with any type of daunting project, from the urgent to the mundane. Product managers are simultaneously big picture and detail oriented, and entrepreneurs also have to balance both of these skillsets. From start-to-finish, I’m going to outline how you can replicate these traits so you can be your own product manager, and build a strong foundation for your business.
Have a System
When you’re running a company and managing your own time, the ability to retain perspective on the big picture while getting stuff done day to day can be overwhelming. Some people are naturally more visionary thinkers and others are more comfortable executing. It’s tough to do both.
For those of us with that gap between our dreams and our to-do lists, there’s a simple fix: build a system to span that gap. Start from the top, plot out your goals, and break it down until your dreams are presented to you daily in manageable tasks on your to do list.
Vision > Strategy > Goals > Roadmap > Tools > Do the work
From big picture to the nitty gritty details, you want to build a framework that’s right for you. It’s systems all the way down.
But first, it’s important to remember that no system is one-size-fits-all. Some people get stuck trying to force their work into established productivity systems. This is a mistake, but a common one.
Your work and your flow are unique, and so should your system be as well. It’s less overwhelming this way, too—it removes the pressure to conform to external standards. Sometimes we get caught up in trying to replicate other people’s success, forgetting that our differences are actually our competitive advantages.
The brilliance of being your own product manager is that you decide how you want to work, so don’t make things harder than they need to be. A good system doesn’t get in your way. It fits naturally into your workflow and it guides you forward. Play with tools, learn about different systems, take the pieces that work for you, and make it your own. Getting Things Done and the Bullet Journal are two popular productivity systems, but there are plenty to choose from.
It’s good to regularly review and evaluate your process and your tools, throw out the bits that aren’t working, tweak the bits that are, and play with it. Experiment with new tools, techniques, minor adjustments, wacky ideas, and keep messing with it until you’re having fun.
Have a Vision
Product managers have the unique role of looking both backwards and forwards, never losing sight of the vision. This is a key skill to hone for any entrepreneur. It’s easy to get lost in the weeds, only to realize on some particularly stressful afternoon, “Wait, what am I even doing right now? And why?”
We have a natural instinct to tend to the most urgent tasks without giving thought to the most important tasks. The important-but-not-urgent tasks are all too easy to push aside to “one day,” but that is often our most impactful and meaningful work. We have to set aside time for looking ahead, for reflecting, and for critically examining how the work we do supports our goals (or not).
Stephen R. Covey wrote the excellent book 7 Habits of Highly Effective People — a must read for everyone. One of the concepts he discusses is the time-management matrix, which outlines a way to prioritize your tasks. It looks like this:
By following this framework, it becomes so much easier to understand your true priorities. And that’s the way out of the weeds: understanding how the work and the details fit into the big picture. Everything you do should feed into your larger goals. For product managers this is second nature.
Regularly take a step back and ask yourself questions like:
- What will this task or project accomplish?
- How important is it?
- How does this support my long-term goals?
Getting organized at the beginning of the year
The point of asking these questions is to uncover the purpose of what you are spending your time on. Running a business is a lot of work, so you really don’t need to be adding extra work to your plate if it’s not directly relevant to your goals. If the answers to these questions are unsatisfactory—if they don’t reveal how the task relates to your vision—reconsider whether you should be spending your time on the task at all.
Writer Neil Gaiman once described in a now-famous keynote speech that he always tried to think of his goal of becoming a successful author as a distant mountain he was moving toward.
“I knew that as long as I kept walking towards the mountain, I would be alright. And when I truly was not sure what to do, I could stop, and think about whether it was taking me towards or away from the mountain.”
This is the essence of prioritizing: understanding how my to-do list, the daily slog, will help me get where I want to go. Life is busy enough already—as an entrepreneur, one of your main tasks is to radically prioritize, focusing on high value areas and forgetting about or delegating the rest.
Aaron Holland, a serial entrepreneur, startup mentor, and founder of Season Share, has adopted the Navy SEAL technique of “front sight focus” as a tool to help him manage priorities while running multiple businesses. Aaron says, “In a firefight where you’re outnumbered by the enemy, you focus on taking down one at a time. I manage my teams the same way. Multitasking is a myth, and the only way to accomplish big things is to put your full attention toward one goal at a time.”
By having a specific strategy to evaluate priorities, Aaron is able to keep a laser focus on his ultimate goals on a daily basis.
Another benefit of looking at the big picture holistically is that it’s easier to see where you can kill two birds with one stone, so to speak (bloody metaphors today!). If you pull your head out of the daily problems and are able to look critically at your business as a whole, you’ll often be able to identify areas where you can solve multiple problems with one solution, likely saving a ton of money and time in the process.
That leads me to my next point…
Practice Strategic Thinking, Always
Good product managers practice systems thinking, which is exactly what it sounds like: viewing everything from the perspective of the system and how everything fits together. It’s the ability to work through decisions strategically, and to trace cause and effect down the line. Great product managers are reasonable and rational in their assumptions and expectations, rely on evidence instead of intuition, and as a result the system runs smoothly.
Making decisions is hard and it doesn’t get any easier when you are running a company. So it’s essential to have a strategy for decision making.
Some of us have a tendency to see a problem, and jump in and try to fix it immediately which is a fine instinct to have. But when facing a complex problem, jumping in immediately will often result in no solution and a lot of wasted time. If you’re using systems thinking, the first step is to understand a problem before you try to solve it.
It may seem obvious, but it’s often counter-intuitive to take a moment for deep thinking once the shit has truly hit the fan. But that’s precisely when you need to take a step back and understand what’s really going on, and then take the steps to fix it.
Rely on evidence, not intuition. Product managers are constantly talking to customers and looking to data to guide their decision-making processes. Get feedback from outside, objective perspectives (but don’t forget to consider the biases these perspectives are subject to), look deeply at the data you have on your business, treat everything as an opportunity to learn, and face the hard truths of cold, hard evidence. It will guide the way forward.
A good PM is mindful of cognitive bias and logical fallacies. Confirmation bias, the sunk-cost fallacy, outcome bias, recency bias, and many other biases can have a disastrous effect on a budding business.
These skewed thought patterns can warp your perspective in the best of times, and a good entrepreneur is able to look at any situation logically and objectively. We are all susceptible to cognitive bias, and it can be hard to dissect our thoughts to the point where we can clearly see these types of patterns.
Mindfulness meditation has been shown to reduce the sunk-cost fallacy, and likely helps with other cognitive biases as well. In addition, the very act of being mindful—aware—of your thought process, whenever you can, has also been shown to reduce cognitive bias and other harmful patterns.
It’s an act of slowly training your brain, over time, to recognize where your judgement might be clouded or your reasoning not so sound. And as you become aware, fallacies become easier and easier to avoid.
We’re big fans of mindfulness meditation here at Foundr (we even dedicated a whole magazine issue to it!), and yes, it can even help your product management skills.
It sounds hard, but it’s actually super easy to get started. It’s just a matter of developing a habit of observing your thought process. Our thoughts can trick us, make no mistake. Mindfulness is all about paying attention to your mind, and observing your thoughts and feelings without judgement. That’s it. With that understanding, you’ll be miles ahead of most people.
I’ll give an unrelated example of how you can apply mindfulness in daily life. I’ve been trying to have better posture, and one way to do this is to be mindful of when my posture has slumped. So when the thought of posture crosses my mind, I take note, and take advantage of the reminder to correct my posture. Over time, the thought crosses my mind more and more—that’s just the way brains work. I’m quite literally training my brain to think of my posture, and after a while it becomes second nature.
Break Down Your Goals
You probably know that to pursue your vision, you need to set goals that are realistic and measurable. But often we struggle to connect these goals to our daily work. That’s where a roadmap comes in handy. It helps you visualize your progress and break down your goals into manageable chunks. As you do this, your priorities will become crystal clear.
There are many different strategies and ways of going about this. I’m a visual person, so I like to map this kind of stuff out on a whiteboard or a large piece of paper. Doing it by hand, at least at the beginning, helps me see how everything fits together. But everyone processes information differently, so you might want to use an app, a spreadsheet, or a specific framework.
It doesn’t matter how you do it—everyone has a different style, and like I mentioned, nothing is one-size-fits-all—you just need to put in some time tracing the path from your goals to smaller and smaller goals, until you have manageable chunks: ideally 30-120 minutes per task.
This is where the product manager analogy comes into play again. When running a company, you have the same responsibility to connect the dots between the vision and the day to day, plotting your course carefully instead of running around in the dark.
A few things to remember:
- Don’t think about how things are done, but instead think about what needs to happen, and when.
- Focus on the highest value projects and tasks, the ones that will help you achieve your vision as quickly and efficiently as possible.
- Identify the low-hanging fruit (it’s a cliche for a reason, and it’s delicious), and go after that first. It does wonders for morale, for you and your team.
Once you have your roadmap, it’s time to build out a toolset that will help you along the way.
Build Your Toolset
While you don’t want to get too crazy and give yourself unnecessary work, having the right set of tools that works with your system is a game-changer. A good product manager will support their system with a set of tools that fit into the team’s workflow without bogging anyone down.
I’ve always been app-happy, but lately I’ve been trying to simplify and consolidate the tools I use, to streamline my work process. At the same time, I’ve been working on automating or finding tools for tasks that I find myself doing over and over again. Here is a handy guide on when to automate a task:
The tools you need depend heavily on your industry and type of business, but there are a few needs that apply to everyone.
Hopefully you already have system for documentation, but as an obsessive note-taker, I’ve been surprised to encounter many entrepreneurs who flat out don’t, or who rely on a sloppy system spread across multiple platforms. If you’re serious about a project, you need to have one central location for documentation and notes.
Historically, I’ve used Evernote for this, but any app will do, as long as it’s searchable. With all of my information in one place, looking up something from three years ago is as easy as opening the app and entering a keyword or two. This has saved my life multiple times and everyone, especially entrepreneurs, needs a central place for information.
All of the information for my music blog is in one place, so I can find anything I need in seconds
Everyone has a different favorite to-do manager, but the key is that you need one—it’s the linchpin of any system. Ideally, you can update it from your phone and computer and have different buckets of lists for different projects. Do some research and find one that fits nicely into your workflow. Apps like Asana and Trello are more collaborative, while apps like Todoist and Wunderlist are great for personal task management. Play with them, pick one, and mold it to your will.
Save for Later
I love Pocket for this concept. I can easily stash any website or article for later from any device, any app. With the browser extension and mobile share, I can quickly save an article without leaving the app I’m in or disrupting the task I’m working on. This allows me to get through my email inbox much, much faster.
Adding to Pocket via right-clicking on an email link — easy peasy!
Most people use these services for keeping up with the news or blog posts, but it’s a great entrepreneurial tool too. I throw everything in there, from articles that catch my eye to instructions and research to various “to dos” that aren’t urgent. Because I throw everything in one central place, and Pocket is searchable, it’s so easy to resurface. I don’t have to organize anything, it just sits there until I need it or have a spare minute to read (synced to every device, of course). You can organize by folder, as well.
The best thing about a system like this is that it saves me so much time when doing research or working through my email inbox. Something looks interesting? Save it for later, and move on. Inbox zero and no open tabs, here I come!
Last Step: Do the Work
While the above may seem like a long process, it’s only as long as you want it to be. The important thing to remember when you need to be your own product manager is the concept of deliberately thinking through your business and your goals to identify the best way forward. Once you’ve done that, it’s time to do the work, and don’t forget to finish what you start. As you work toward your vision, track your progress through your roadmap. Tweak your process. And have fun!
This is my system. What system or process do you use to organize your life as an entrepreneur? Let us know in the comments!