Productivity for Entrepreneurs

I was talking to a friend recently about our holiday breaks. I took two weeks off without any issue, but after just a few days off, things in his business had started to fall apart. He couldn’t enjoy the last half of his vacation because he had to put out a million little fires and get back to work.

Unfortunately, my friend’s vacation was not unique.

Most entrepreneurs start a business because they crave the freedom of having their own schedule, being their own boss, and enjoying the work they do, but many get so “busy” that they can’t enjoy any of the freedom they wanted in the first place. Their input is needed every day and they don’t have the discipline to let things go, so they’re stuck on a treadmill of doing without producing real results.

You Don’t Need More Time

The problem is not that these struggling entrepreneurs need more time, but that they need to use the time they have more effectively.

If you want to build a successful business that buys you freedom, you have to stay focused on the things that matter most. You have to learn to automate, drop, or delegate relentlessly. You have to know where every hour of your time is going.

In this post, I’m going to share my productivity formula. It’s helped me quickly grow my business, but it also helped me build a successful career as an engineer and CTO before this. While each of these practices seems easy, surprisingly few people actually do all of them.

Because this is a long one, I’ve divided it up into five sections:

I don’t think you have to be a productivity czar just to run a successful business, but if you want to capture more free time while building a company, these practices will put you on the right path.

Time Management

I’ve never met an entrepreneur who didn’t struggle with time management. As an entrepreneur, you likely have many more ideas than you have time, so you’re bound to face the question, “How will you spend your limited hours?”

I think this is the most important question an entrepreneur can answer.

Wasting time on low-value, energy-sapping tasks is why so many solo founders burn out before they can build a sustainable business. I mean, why would someone stick with running a company if they hated it and had to work for 20 hours a day? It’s illogical.

So, your goal for time management should be maximizing the hours you spend on high-value tasks that give you more energy. Here’s how you can do it:

1. Track Your Time

Most people have a very bad sense of how they’re actually spending their time. They assume they’re being productive and that they just need more hours in the day, but almost everyone’s assumptions are wrong. You can’t improve how you’re managing your time if you don’t actually measure it.

Fortunately, this is one of the easiest things to do in this whole list; you just need to get in the habit of clicking “Start” on your time tracking app every time you do work. I use Toggl, but there are hundreds of options for time tracking, so pick whichever resonates with you.

Once you have an app, create categories around the jobs you do. I update these categories every 3–6 months as my role in the company changes, but right now, they are:

  • CEO/Big Picture — Partnerships, company leadership, vision, tracking, coaching leaders
  • Administrative — Email, paperwork, taxes, payroll, etc.
  • Sales and Account Management Leadership — Managing sales and account teams, giving them feedback, checking on the status of their projects, and coaching team members
  • Marketing Leadership — Strategic marketing initiatives for the company and overseeing tactical work done by contractors and team members
  • Operations — Weighing in on tech reviews, editing, or working directly on production for clients

Next, set goals for how much of your time you’d like to go to each category. My goal is to spend 40%-50% of my time being a “CEO” with the others taking up 10–20% each.

I get a report from Toggl every week with a breakdown of how I actually spent my time. Here’s an old one from last year before I updated my categories.

In addition to using these categories and the weekly report to understand how you truly spend your time, tracking forces you to focus. Because you can only attribute each moment of time to a single task, it’s harder to switch back and forth while accurately accounting for your day.

Finally, I use my time breakdown to decide when I need to hire someone and to improve my delegation skills. For example, when “Marketing Leadership” becomes a 15–20 hour per week job, I will start the process of hiring someone to take over that task as I won’t be able to keep up with it much longer.

2. Block Your Calendar

Another thing I don’t understand is entrepreneurs who are always available through Slack, calendar invites, or email.

They probably want it to be very easy for customers and teammates to ping them, but being overly responsive sets a bad precedent. People won’t learn to solve their own problems if you’re always 2 minutes away.

Similarly, if you do sales meetings and prospects see that you’re 100% available, they might assume you’re not very busy or that you don’t have many other customers. There’s actually value in percieved scarcity, so being overly available might make you less desireable.

I only allow three afternoons and one morning per week for calls now. I used to be a bit more available when I was leading all our sales meetings, but I’ve found that having more focus time is more valuable than being immediately available.

Another thing that’s easy to do is skip important tasks like working out, eating healthy meals, or spending time with family. I block these activities on my calendar as well so I can be sure I always find time for them. My energy level and effectiveness drop off significantly when I get out of balance.

3. Build Systems for Focus

In addition to blocking time for thinking and doing deep work, there are a few other things I’ve found helpful for maintaining focus.

  • Remove extra browser tabs, notifications (more on that in the next section), apps, and “digital clutter” that might distract you.
  • Break projects down into 2–4 hour blocks. As a business owner, you’re not going to get 40-hours of focus in a week, so creating massive, multi-week projects will take you forever. Having smaller chunks of work keeps things manageable.
  • Work an off-day. For example, I work Sunday and take Wednesday off. The advantage is that nobody scheduled meetings on Sunday, so I have a whole day of focus time where I can make progress on big projects.
  • Set up a dedicated workspace. If you don’t have an office, at least use a specific part of your home so that the environment isn’t distracting or difficult to work in. You should also keep it clean.
  • Dedicate time for chores and errands. Don’t let yourself do them anytime you think of them because they’ll eat up your day quickly, making you feel busy without actually being productive.
  • Finally, minimize the number of assets you have that take time and mental energy to maintain. I understand the appeal of buying a house, boat, fancy car, or rental property, but I see all of these “assets” as time-consuming hobbies. Sure, they might make you money eventually, but they aren’t free to maintain.

4. Change Your Mindset on “Unproductive” Time

I’m borderline obsessed with improving my productivity, but that doesn’t mean I never have downtime. On the contrary, some boredom is actually a good thing and having hobbies outside of work will make you a more interesting person.

But rather than think of activities like playing the piano, baking, or sitting quietly as a waste of time, I use them to recharge. The more focused and productive I am in the “on” time, the more “off” time I get to build motivation and enjoy life.

Information I/O (Input/Output)

Once you have a habit of tracking your time and you’ve built systems that allow you to focus, you need to manage the input and output of information. Email, Slack, and social media will never stop sending you inputs, so you need to control this firehouse.

I can count on one hand the number of emails that required my response in less than an hour, so unless that’s part of your key business differentiator (and if it is, I’d rethink it), stop checking notifications in real-time. Batching these information input tasks will save you hundreds of hours every year and help you focus better on bigger projects.

1. Turn All Push Notifications Off

Push notifications give the power of attention to your devices so that whenever they want it, they can buy it with a ping.

Turn this around. You own your attention, but you might lend an hour of it to your email inbox every day.

Turn all notifications off and then enable only the ones that you need for emergencies (for me, it’s phone calls and texts because that’s how my wife reaches me). I set all other app notifications off.

Next, put time on your calendar to check the apps you need to. I still check my email twice per day, but I’m not constantly in my inbox waiting to respond to things. This means my team might have to wait a few hours for a response from me, but it also means they’ll try to solve the problem without me first, which is what I really want.

News alerts are equally bad. Do you really need a push notification when a new supreme court nominee is made? I’ll get to my solution for news in a minute, but the first step is to opt-out of push notifications.

Once you own your attention, it’s time to tackle your inbox.

2. Tame Your Inbox

Next, archive everything you don’t need to respond to and get to inbox zero.

Your email inbox should have just a few unread messages in it each time you check it. When you do check your email, decide if each one is:

  • Trivial — emails where a response can take less than two minutes can be handled immediately
  • Urgent — emails you need to respond to by the end of the day
  • Not urgent — emails you can respond to by the end of the week
  • Informational — emails with responses or info you need for another project (ideally kept in your project management tool of choice)

I like using different colored stars and folders to keep my inbox clear, but decide what works for you. The important bit is managing the inbound flow of information and not letting it pile up or lose track of important messages.

If you use Gmail, filters are a fantastic way to improve your workflow. Most emails I get are picked up by a filter and automatically archived before I even see them. This is part of the reason I’ve avoided adopting Slack since I started my own company.

3. Batch the News You Want

Many entrepreneurs think they need to keep up with news, but it’s probably not as important as you think.

Tim Ferriss of 4-Hour Workweek fame advocates never checking the news but instead just talking to people about what’s going on. They’ll usually be able to fill you in with more relevance than click-bait journalists will.

I mostly agree, but I also like keeping up with some local news and industry newsletters, so I’ve created a folder in my Gmail exclusively for news. Then, I subscribe to newsletters and set up a filter to send them straight to that folder.

This means I can check the news every week via my inbox. No more social media news or alerts or scrolling Google News. With the rise of Substack and Revue, there are more great newsletters than ever before, so it’s much easier to opt-in to news that’s relevant and only available when you want it.

4. Check Social Media Weekly

The best way to sap your energy and motivation is to fall into doomscrolling every night before bed.

That said, if you need social media for work, you might not want to delete all your accounts. We get a fair number of clients because of my presence on Linkedin and Twitter, so I’m not unilaterally opposed to social media.

Instead, I set a reminder to check my social accounts and professional Slack channels twice per week. I timebox the interactions so they won’t go on endlessly, but give myself plenty of time to respond.

I also use a scheduling tool to make it look like I’m active all week, but in reality, I write all my posts ahead of time.

As a business owner, you have to be both strategic and reactive, but the ratio is way off for many business owners. They’re almost 100% reactive and very rarely able to carve out time for strategic thinking and projects. Turning off notifications and using set times to check for events you need to react to allows you to be strategic first.

Maintaining Relationships

With all this talk about productivity, I’d like to point out that this doesn’t mean you have to be a robot. Entrepreneurs need relationships with other humans, and not just for professional advancement.

If you don’t invest in genuine, long-term relationships with people, no amount of professional success will fulfill you. While many people are good at organically meeting with friends and spending time with family, I struggle with this, so like most things in my life, I have a system for it:

1. Build a List of People You Want to Stay in Touch With

Mine has 50–60 people on it at any given time and includes friends, family members, former co-workers, and others who I find fun to keep in touch with. I am not connected on social media with many of these people, so our primary interactions are intentional.

Each week, I reach out to whomever I haven’t spoken with in the longest time and see if they want to get together. Sometimes (especially lately given the pandemic) these are virtual meetings, but I try to get together in person when possible.

2. Set Aside Family Planning Time

My default mode is heads-down, in my laptop working. So, when I get a free evening, I’ll probably be on my computer doing something.

This became a huge issue for my wife and me as her default is to talk or hang out with me. During pre-marital counseling, we established a weekly family planning time so we could coordinate which nights we’d hang out and which ones we’d be on our own.

This family planning session has become even more essential now that we have a child and dog to include in the plan.

3. Travel for People, Not Places

I used to travel alone a lot. There’s nothing wrong with taking solo trips, but I realized recently that it was far less fulfilling than traveling with someone or traveling to someone.

Now, I try to plan my travel around the people I’m going with or the people I’m going to see while there. With friends and family all around the world, it’s not hard to have a great list of people to visit and these trips are often much more interesting than getting stuck in tourist traps alone.

Efficient Meetings

My first internship in college was at a huge, global corporation. As an intern, I didn’t have many meetings, but my boss would be booked back-to-back all day at meetings that easily could have been an email.

At this company, being in meetings was a sign of importance and being double-booked for meetings was a sign of real power. This is a toxic reality in corporate life, but as an entrepreneur, your meetings don’t have to suck.

1. Send an Agenda Before

This is such a basic but surprisingly underused tool for meetings. Taking 10–15 minutes to write a good agenda and compile any pre-meeting research (see the next step) can save a ton of time, and it often leads me to cancel the meeting altogether.

I tend to include my agenda in the calendar invite before each meeting and then update it in the days leading up to the event. Then, I let everyone know that the agenda is finalized the day before and to reply if they have other suggestions before the call.

Having an agenda shows that you respect your team’s time and let’s people see if the issues they care about are even going to be discussed.

2. Compile Research Before the Meeting

There’s nothing worse than watching someone stumble through a spreadsheet during an all-team meeting. Just think of how many wasted hours (and dollars!) are on the table when you’re not prepared.

Research should be compiled and organized before the meeting, ideally sent out early with the agenda. If new questions come up during the meeting, don’t look them up in real-time, just make a note to follow up.

3. Replace Meetings With Videos or Emails

Depending on the amount of 2-way communication you expect in the meeting, you might be able to replace the entire thing with a Loom video or an email. I also find that recording or writing my points out helps me prepare, so even if they don’t replace the meeting, they might help me be better equipped and efficient.

Think about alternatives for standing meetings too. For example, we don’t do a real-time daily standup, but instead, we use StatusHero to asynchronously keep each other informed.

4. Set Goals/Takeaways

When people leave a good meeting, the takeaways are clear. Meetings should not be held arbitrarily, but there are a few legitimately good goals for meetings:

  • Make a difficult decision
  • Rally people around a common cause or objective
  • Hold a retrospective: what did you learn?
  • Mentorship, coaching, or performance reviews

Meetings for status updates or “touching base” are rarely necessary.

Delegating and Outsourcing

Delegating tasks to other people is surprisingly difficult. That’s why so many entrepreneurs struggle to hire or remove themselves from their businesses. But, once you figure out a pattern for finding tasks to delegate, finding people to do those tasks, and defining them thoroughly, it will completely change your effectiveness.

1. Decide What to Outsource

Some tasks are markedly easier to outsource or delegate, some are easier to automate, and some simply must be done by you.

While tracking my time, I look for time spent on low-level, tactical tasks that sap my energy. For example, mundane tasks like running payroll or updating social media are two things I frequently outsource.

You can also find tasks in your personal life to delegate. For example, I don’t like cleaning or making lunches, so I pay services to do these tasks for me. Once I realized that my effective hourly rate for work I enjoy doing is 10x higher than how much I’d have to pay someone to clean or cook, it was an obvious choice.

Some tasks seem like they’d be easy to outsource, but actually aren’t. For example, you can hire a bookkeeper to help you, but as a business owner, you’ll need to keep a close eye on your books and taxes if you want to understand your business and stay out of financial trouble.

2. Decide Who Should Do It

I use three different classifications to decide who should take over the task at hand:

  1. Freelancers are good for isolated, short-term, or repetitive tasks that are easy to replicate and relatively low-risk. For example, social media updates, graphic design, and back-office paperwork are all good tasks for freelancers to handle.
  2. Agencies are more expensive, but give you redundancy and increased capacity. For example, we use agencies for backlink building, public relations, and cleaning my house because they are more important and more complex tasks that often require a few different people. Plus, an agency has a reputation to protect and more legal coverage that can protect you if something goes wrong.
  3. Employees are best reserved for poorly-defined, high-level, high-value, and high-risk tasks. For example, customer relationships should almost never be outsourced to freelancers or agencies as they’re one of the most critical pieces of a business, but as the founder, you can’t do customer support forever.

Cost is also a factor. The allure of hiring an inexperienced freelancer for a few dollars per hour quickly runs out when you realize you’ll spend hours explaining each step to them. At the same time, you also don’t want to overpay for relatively low-skilled labor.

For this reason, small companies should rarely hire junior people, instead opting for either specialized freelancers or agencies or mid-level employees who are on a trajectory into leadership roles.

If you can’t find a way to delegate a task cost-effectively, you probably just need to stop doing it entirely. It’s no better for you as a business owner to work on a task without a positive ROI than it is for a freelancer or employee to do it.

3. Define the “How”

Finally, depending on the task and skills of the person you hire, you need to define how you want the task done. Many entrepreneurs don’t realize how specific they need to get, especially if you hire a low-cost, inexperienced freelancer.

For example, I hire a lot of writers, but before they write an article, I have to spend nearly an hour writing a one-page brief for each post. This includes research, example articles, an outline, and details about the audience. Some freelancers figure out how to do this on their own, but you can’t expect it on their first try.

Loom is really nice if you like recording yourself instead of writing, but I’ve found that some people lose focus when watching videos. So, you should probably have an outline and check their work as well.

Practice Productivity

Like most skills, you won’t go from zero to expert overnight. I’ve been re-learning piano again and I find that the key to getting better is daily practice. Productivity is the same way; you can’t just go on a spree once per year.

Finally, if you’re an entrepreneur who’s looking for more tools or books to help you on your journey, I’ve got plenty of suggestions:

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