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5 Common Habits of Effective Startup CEOs

5 Common Habits of Effective Startup CEOs

Being the CEO of a startup is a lot of hard work. You need to manage the inevitable chaos, wearing multiple hats as a leader,[1] a thinker,[4] and a doer.[2] It can easily be overwhelming when you need to balance everyday tasks alongside the “big picture” tasks that drive the vision and the future of your company.

Once a startup gets some traction, CEOs have to transition from “doer-in-chief” to leading the company and managing the big picture projects, products, cash flow, team culture, and generally becoming both the metaphorical anchor and captain of the ship. But when your company gets to this point, how do you remain an effective CEO?

Any CEO of a startup will tell you that there is no “typical” workday, but after doing some research I’ve found that many CEOs share quite a few habits that make them successful. Let’s take a look at these common habits and how you can use them too.

Organize A Schedule

One habit (some might call it a skill) of effective startup CEOs is to get organized. Really organized. They’ll make a daily schedule and follow it religiously.

Jason Zook, of Jason Does Stuff, is a vocal advocate of time-boxing.[3] He claims that “blocking off time on my calendar keeps me laser focused and highly motivated.”

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Kate Finley, CEO of Belle Communications, prefers to color-code her schedule,[5] assigning different colors to big-picture topics and scheduling blocks of time for social media, emails, project development, meetings, and even exercise and personal time.

An hourly schedule can prevent you from getting distracted from random tasks while giving you peace of mind that you’re spending dedicated time on your company’s needs. Find the best time to schedule out your day and make this skill a habit.

Compartmentalize Company Needs

One of the things that we’ve noticed effective startup CEOs do is that they successfully compartmentalize the different needs of their company. They focus on the specific areas of their business, setting aside time for product development, team building, and financials.

Fetchnotes CEO, Alex Schiff, has a daily meeting with his team. Schiff says this time is critical for his organization, in that it provides a “cross-functional view of what’s happening in the company.”

Finley takes time daily to work on media relations, team and project development, and general communications, while Ryan Carson of Treehouse compartmentalizes business needs by day. He meets with one manager to review product needs on Mondays, while saving sales and marketing for Thursdays.

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By blocking out time for managing your team and different departments you can be sure that you’ll cover all of your big picture needs while saving time for those other random tasks that inevitably arise.

Do Deep Work Early In The Day

More than one CEO, we found, prefers to concentrate on big-picture business strategy in the morning while leaving meetings for the afternoon.

Says Finley, “I find that [mornings are] best to get the majority of my work done before noon and save time for meetings later in the day.” Michael Karnjanaprakorn, head of Skillshare, goes so far as to schedule meetings only a few days a week, to maximize time for deep work and planning.[6] Once a month, he assesses his calendar and reviews what meetings are upcoming and cancels the inefficient ones. Karnjanaprakorn claims that this process “allows me to be proactive and control my time, instead of being reactive to my calendar.”

Make sure to carve out some space in your schedule in the mornings to do the most important strategic work, while your focus and willpower[7] are at their peak. Review your calendar regularly and cut out or reassess what’s ineffective.

Make Time For Family And Celebration

Startup CEOs know how important it is to take time for personal needs, family time, and celebration.

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Ryan Carson includes family time[8] as part of his daily schedule. Schiff makes time for fun with his team,[9] taking them out for laser tag after the successful completion of a major milestone.

Karnjanaprakorn uses a concept from Tim Ferris called “screen-free Saturdays,” where he refuses to work on his laptop or computer and only uses his smartphone for maps and communication with friends and family.

Separating yourself from your work can give you a much-needed mental break and allow you to approach the next work day – or the next week – with a fresh mind. Again, the easy task is to make more work for yourself; the hard task is taking some time to enjoy your success and spend time on yourself.

Give Your Schedule Space For Reflection

Startup CEOs know that it’s important to take care of themselves because it’s easy to feel like there’s always more work to be done.

“I like to have some time to myself free of office distractions to map out an agenda for what I want to accomplish each day. If I don’t, I find that I’m victim to the whims of whatever random task pops up,” says Chris Myers,[10] CEO of fintech BodeTree.

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There’s always something on your to-do list, and it can be difficult to turn off that part of your brain, even for a short amount of time.

Taking time out of your day to meditate,[11] reflect,[12] journal,[13] or just decompress,[14] is an important factor for success. You’re nurturing both physical and mental well-being, which will do nothing but benefit you and your startup in the long run.


In brief, successful startup CEOs make the transition to a flexible, organized position and focus on the big picture, leading their teams to success. Depending on your personal habits and schedule, create a system that works best for your needs, while saving time to enjoy your hard work.

Featured photo credit: Brooke Cagle via unsplash.com

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Keith Shields

CEO, Designli

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Last Updated on September 23, 2020

Do What You Love and Love What You Do to Achieve More

Do What You Love and Love What You Do to Achieve More

Are you waking up each day looking for that perfect thing, activity, or job that will make your life work? Or, maybe you are looking for that perfect relationship. Once you “get” this new thing that will allow you to do what you love, you are sure that you will be happy forever.

In reality, life doesn’t work like that, and we would probably get bored if it did. There is likely no one thing, experience, or activity that will keep you feeling passionate and engaged all the time. What’s important is staying connected to what you love and continuing to grow in the process.

Here, we’ll talk about how to get started doing what you love and achieving more in life through the motivation it brings. Doing this doesn’t have to take a long time; it just takes determination and energy.

Most People Already Know Their Passion

So many people walk around in life “looking for” their passion. They look for it as if true passion is some mysterious thing that is difficult to find and runs away once you find it. However, the problem is rarely lack of passion.

Most of us already know what we love to do. We know what excites us, even if we haven’t done it for years. Instead, we focus on what we think we “must” do.

For example, maybe you love building model cars or painting pet portraits. Yet, each day you work a completely unrelated job and make no time for the activity you already know you love. The truth is you probably don’t need to find your passion; you just need to start doing what you already know you’re passionate about[1].

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No Activity Is Exciting All the Time

Even people who are living their dream lifestyle or working their dream job don’t love it all the time. Every job or lifestyle has parts of it that we won’t like.

Let’s say your dream is to become an actress, and you succeed. You may not enjoy the process of auditioning and facing rejection. You may experience moments of boredom when you practice your lines over and over again. But the overall experience is totally worth it.

Most of life is like that. Don’t set yourself up for disappointment by demanding that life be perfect all the time. If things were perfect and easy, you would ultimately stop learning and growing, and life would begin to lack even more meaning in that case.

Be grateful for both the good and bad moments as they are both entirely necessary if you genuinely want to do what you love and love what you do.

Doing What You Love May Not Be Easy

Living a life you love is unlikely to be easy. If it was, you would not grow very much as a person. And, if you think about a great book or movie, the growth of the main character is what matters most.

What if the challenges you meet along your path to living a life you love were designed to make you grow as a person? You may actually start looking forward to challenges instead of dreading them. An easy life hardly ever makes a compelling story.

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If you struggle to overcome challenges, try writing them down each time you encounter one. Then, write down three ways you could tackle it. Try one, and if it doesn’t work, try another. This way, you’ll learn what does and doesn’t work for you.

How to Do What You Love

There are many small steps you can take to ensure you are making time to do the things you love. Start with these, and you’ll likely find that you’re already on the right track.

1. Choose Your Priorities Wisely

Many people claim they want to do something, yet they don’t do it. The truth is they might not really want to do it in the first place[2].

We all end up following through on what matters most to us. We make decisions moment by moment about what we need to focus on. What we choose to do is what we deem most important in our lives.

If there is something you claim you want to do but you don’t do it, try asking yourself how much you really want it or where it’s currently placed on priority list. Are there other things you want more?

Be honest with yourself: what you currently do each day is a reflection of your priorities. Recognize that you can change your priorities at any time.

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Make a list of your priorities. Really take the time to think this through. Then, ask yourself if what you are doing each day reflects them. For example, if you believe your top priority is spending more time with your family, but you consistently take on extra hours at work, you’re not really prioritizing things in the way you think you are.

If this is happening, it’s time to make a change.

2. Do One Small Thing Each Day

As stated above, doing what you love doesn’t have to mean finding that perfect job that makes you want to jump out of bed in the morning. If you want to do what you love, start with one small thing each day.

Maybe you love reading a good book. Take ten minutes before bed to read.

Maybe you love swimming. Get a membership at the local YMCA, and go there for thirty minutes after work each day.

Dedicating even a short amount of time to something that brings you joy each day will improve your life overall. You may find that, over time, a career path related to what you love to do pops up. After doing the thing you love each day, you’ll be more than prepared to take it on when the opportunity arises.

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If you need help making time for your passions, check out this article to get started.

3. Prepare to Make Sacrifices

If you are an exceptionally busy person (aren’t we all?), you may have to make sacrifices in order to make space for the things you are passionate about. Maybe you take on less extra hours at the office or take thirty minutes away from another hobby in order to develop another that you enjoy.

Looking at your priority list will help you decide what can get put on the back burner and what can’t. Remember, do this thinking about what will help you feel good about how you’re spending your time. 

For example, if you love writing but rarely make time for it, consider getting up 30 minutes earlier than normal. Or instead of browsing your phone for 30 minutes before bed, you can write instead. There is always a way to find time for what you love.

Final Thoughts

If you love what you do, each day becomes a joyful adventure. If you don’t love what you are doing, life feels like a chore. The best way to achieve success is to design a life you love and live it every day.

Remember, doing something you love doesn’t have to include big gestures or time-consuming projects. Start small and grow from there.

More on How to Do What You Love

Featured photo credit: William Recinos via unsplash.com

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