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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 July 10, 2020

Feeling Stuck in Your Career? How to Break Free and Get Ahead

Feeling Stuck in Your Career? How to Break Free and Get Ahead

Have you ever caught yourself in a daydream where you’ve gone for that upcoming promotion, and you’re now the boss at work? Or how about the one where you’ve summoned up all your courage to quit a job where you’re feeling stuck in your career and live your dream instead? Or when you’ve changed career paths to do what really makes you happy?

Then, you snapped back to reality and realized that you’re not the boss, not living your dream, and not even happy in the career path that you’re on.

Over the years I’ve worked with hundreds of individuals who’ve told me they feel stuck in their careers, that something had to change for them to break free and be happy, but they lacked the confidence to take that step. My mission is to make sure that nobody feels stuck in their career because of a momentary lapse in bravery that’s dragged on for too long.

Read on to find out how you can stop feeling stuck in your career, break free, and get ahead at work. .

Here are my top ten tips for becoming unstuck in your career.

1. Make Time for You

If you’re feeling stuck, frustrated, or unhappy with how your career is panning out, the first step is to work out why.

Maybe you’ve arrived in your current career by accident and haven’t ever made time to deliberately think or plan what you’d love to do and how you’d get there.

Prioritizing time to think is the first step you need to take to stop feeling stuck and start getting ahead. Book some time into your day where you can have an uninterrupted meeting with yourself. This is your thinking time.

Work out what makes you happy at work, what doesn’t, and where you might want to go. Decide on the steps you want to take to progress your career in the direction that you want it to take.

For example, are there training days, evening courses, or online learning that you can do? Have you considered getting a mentor to help you get ahead?

By booking in a meeting with yourself, it signals it’s important (to you and your colleagues) and also stops others spotting a gap in your day and filling it with a meeting.

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2. Grow Your Network Before You Need It

Who you know is more important than what you know for career progression. Don’t wait until you’re feeling stuck in your career to start expanding your networks. Do it now.

Adam Grant, the author of Give and Take, says you’re 58% more likely to get a new job through your weak ties than through your strong ones. Your strong ties are those in your immediate circle whom you interact with often. Your weak ties are your friends of friends. They move in different circles to you, they know different people, make different connections, and are more likely to introduce you to new and different opportunities[1].

When I was thinking about setting up my current company, Lucidity, I turned up to every networking event. I drank a lot of coffees with a lot of different people to understand what they did, to ask for advice, to unpick what their problems were, and to look for opportunities for collaboration and connections.

It paid off because, when I launched my business, I let my network know how I could help them, and soon I had my first clients.

Pay attention to building and nurturing your networks and focus on how you can add value to other. That’s where your next career opportunity is most likely to come from.

3. Surround Yourself With People Who Inspire You

According to Tim Ferriss, “You are the average of the five people you most associate with,” and his associations with different people ebbs and flows depending on what he’s working on and trying to achieve[2].

For example, if you are trying to be fitter, it’s easier if you hang around with people who love doing exercise–they help you to up your game.

If you want that promotion, a career change, or to set up your own business, seek out people who are excelling at it already. They’ll have valuable things to teach you about breaking free and getting ahead.

4. Work on Your Personal Brand

Jeff Bezos defines a personal brand as “what people say about you when you’re not in the room.” People will talk about you when you are not in the room anyway, so you might as well be deliberate about what you’d like people to say!

Your personal brand isn’t about pretending to be something you’re not. That can actually keep you feeling stuck in your career. It’s really about being your best “real you.” It’s about owning your strengths and being purposeful about how you want to be perceived by others.

What do you want to be known for? By being more deliberate about how you want to come across and what you’re looking for in your career, you’ll increase your chance of attracting the right opportunities.

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Once you’ve given your personal brand some thought, make sure that you show up online. Is your LinkedIn profile up to date? And if you don’t have one, get one. Make sure it communicates what you want to be known for and that it’s consistent with your other social media profiles.

Try these 5 Steps to Master Networking Skills and Perfect Your Personal Branding.

5. Be Accountable

Achieve your career goals faster, and grow and learn by making yourself accountable. Tell other people your goals and a timeline. and have them to hold you accountable.

For example, you might want to get a promotion by the end of the year, have decided the sector you want to move to by the end of the month, or have got your new business idea before the next pay day. Whatever your ambitions are, you can tell a friend or a colleague, or share this with a mentor or a mastermind group.

When we tell other people our goals and intentions, they hold us accountable, and we are more likely to make progress faster.

6. Make Sure Your Values Are Aligned With Your Company’s

All the professional development, goal setting, and networks in the world won’t make you happy if you’re working for a company that ultimately has opposing values to yours.

Figure out what’s important to you in a job. For example, does your company’s product help people live a better life? Do you feel strongly about your company’s ethics and social responsibility? Does the company culture allows employees to be themselves and shine? Or maybe flexible working and more holidays for employees with families is where your heart is?

Some companies put their employees well-being at the core of their business; others put profits first. If you feel that your values don’t match the core values of your employer, it could be a reason why you’re feeling stuck in your career and unhappy.

It’s important to work through this and identify whether it’s the job that is not right for you, or if it’s a great job but the organization or sector is wrong for you.

7. Get out of Your Comfort Zone

Your comfort zone is your safe place. For any change to happen, you have to step out of your comfort zone.

It’s actually much easier not to change anything and to keep grumbling on about how you’re stuck and unhappy in your career than to step outside of your comfort zone to address the fearful unknowns associated with change. It’s part of human nature that we’d put up with the devil we know rather than risk the devil we don’t.

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This is true even if the devil we know is a boring, unfulfilling job because we’re wired to think that making a change to find a better option might actually leave us worse off.

If you feel stuck, it might be that your confidence has got the better of you.

To get ahead at work, start taking small steps outside of your comfort zone. Consider what you’re scared of that is stopping you from making a change. Then, tackle that in small steps.

For example, if you know that to move into the job you want, you’ll have to do more public speaking, but public speaking terrifies you so much it’s stopping you from going for the job, then start small to build your confidence. You can speak up more in team meetings, then slowly build from there.

You might also choose to set up or be part of a specific group. One of my clients, who found that confidence was holding her team back in achieving work goals, set up a “get out of your comfort zone club,” where they challenge and support each other to build their confidence by regularly leaving their comfort zones.

8. Learn to Embrace Failure

Failure is part of life. A New York University study found that children learning to walk averaged 2,368 steps and fell 17 times an hour[3]. Failure is simply the natural path to success.

The truth is that we don’t get everything right the first time. We fail, we learn, we pick ourselves up, and we try again.

In my experience, it’s common that whilst the theory of learning from failure is supported, the reality of being open about failures to enable personal learning is much harder to achieve.

We don’t like to admit that we’ve failed. We have a fight or flight response to failure. It’s a normal gut reaction to ask ourselves: “Will I get away with it if I don’t tell anyone?” We are fearful of criticism, of losing face in front of others, or even being fired for failure.

However, if you’re going to stop feeling stuck in your career, you must be open to learning from failure.

Reframe failure by viewing everything as an experiment because you can’t have a failed experiment—you just learn whether something works or not. Think of Edison inventing the lightbulb, when he said:

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“I’ve not failed. I’ve just found 10,000 ways that won’t work.”

9. Build Your Resilience

Resilience is the ability to tackle difficulties and setbacks, to bounce back, regroup, and to keep going.

Getting unstuck in your career, taking a different path, and achieving the results you want will take resilience. Having resilience is also the capacity to choose how you respond to the unexpected things that life throws your way and adapt and thrive in times of complex change.

Given that the world we live in is in constant flux, and the only thing that is certain is uncertainty, the ability to adapt and bounce back is an important life skill, as well as a career skill.

In her book Grit: The Power of Passion and Perseverance, Angela Duckworth’s research shows that when measuring success, the ability to persevere beats talent every time.

Learn more about how to build resilience in this guide: What Is Resilience and How to Always Be Resilient (Step-By-Step Guide)

10. Ask for Help

It can be hard to ask for help, as it can make us feel vulnerable.

No one person can be expected to have all the answers. That’s why we need a group of people that we can go to for help, people who can pick us up when we have setbacks and also help us to celebrate success.

My advice is to be deliberate about creating your group. You can do that with a tool called a “Me Map”:

  1. Write down all the things that you might need support with, like help with career progression, interview practice, making new connections, talking through business plans, learning from failure, etc.
  2. Next to each thing, write the names of the people you go to when you need that particular thing.
  3. Make sure you get in touch and regularly connect with them.

Final Thoughts

You can stop feeling stuck in your career, break free, and get ahead at work by applying the tips in this article. Start small by incorporating three new things in your first week, and then adding more as your comfort zone and capacity expands.

Remember, no matter how stuck you feel, it’s never too late to make a change and land the career that you truly want.

More Tips to Stop Feeling Stuck in Your Career

Featured photo credit: NEW DATA SERVICES via unsplash.com

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