Ryan Battles Data-Driven Marketing Specialist

5 Bad Habits that Entrepreneurs Should Break


In my book,  The 9 Habits of Successful Entrepreneurs, I outline a series of regular routines that maximize your energy, save time, and allow you to enjoy consistent wins.

Just as there are habits that should be added to your routine, there are also a few toxic habits that should be controlled. These habits are common to many entrepreneurs, and those who have found success have also found ways to minimize their damage.

Nearly all of these habits originally stem from good intentions, whether it is trying to improve your learning, paying attention to details, or communicating with your team. It’s not necessarily the actions themselves, but the habits we form around them to influence they way we carry out these tasks that derails us as entrepreneurs.

Once we recognize these potential pitfalls, we can apply a strategy to reduce their negative effects on us, free up our time, energy, and remove the cap on our success potential.

Check out The 9 Habits of Successful Entrepreneurs on Amazon

1. Business & Self-Improvement Books

Business & Self-Improvement Books

I love books. I love buying them, I love reading them, and I love writing them! When trying to learn a new skill, few things compare to the thrill of a full Amazon shopping cart ready with the wisdom of those who have gone before me, and written about it.

Here’s the problem…often these books simply take up space on my shelf. There’s a strange psychological event going on that separates the emotions we experience when we think about the potential of owning a book, vs. once we actually own it. In my mind, I envision myself sitting at a coffee shop, reading my new books, and taking copious notes of all of the insight and inspiration that burst from their pages.

Don’t get me wrong, there are many times I do read these books, and I do gain a lot of insight from them. In fact, there are many things that contribute to my success today that I was inspired to try from reading a book.

So why are business and self-improvement books a dangerous habit?

They are a concern because it is really easy to get lost in reading about a certain subject, instead of actually doing it. Reading about a topic can sometimes make us feel like we are making progress towards accomplishing a goal, when in reality we haven’t made any measurable progress.

Want to learn how to cook? Yes, it helps to have a cookbook or two on hand, but reading through 12 cookbooks and never turning on your stovetop just makes you an informed cook wanna-be. The same holds true for entrepreneurship. There are a lot of great books out there on entrepreneurship, but if you never start a business, or try to test things out for yourself, you’ll never gain that experiential knowledge that launches you to success.

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As mentioned previously, these books have their place. They can help you when you hit a wall (due to actually trying something first). Business and self-improvement books are also great ways to relax and take in new knowledge, but only if the bulk of your time is spent putting their tactics into action.

Don’t get tripped up on the habit of reading and learning about growth and success, without also taking the appropriate amount of time to gain real experience.

2. Unoptimized Meetings

Unoptimized Meetings

People love to meet together. We’re social creatures! When available, we also like to solicit the help of others. This is why companies love to have meetings. The problem is, meetings are often the lazy way out. All you have to do is convince a bunch of people to show up in a room together and start talking about an issue at hand. Surprisingly enough, meetings happen every day that don’t actually produce any measurable outcome!

Meetings are not all bad, there are times when they are necessary, but most often they are not. Could you accomplish the same outcome with a group email? How about using a tool like Slack chat to have a quick discussion?

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If there are no other ways to communicate with others than to have another meeting, then the following should be applied:

  1. Have a clear agenda. Never hold a meeting without a clear agenda, and once the meetings starts, dive right into it. Once the agenda has been met, adjourn the meeting.
  2. Minimize the people involved. If there are people who don’t need to be there to accomplish the agenda, don’t ask them to be there. If tasks are only relevant to a sub-group, consider splitting the meeting into smaller ones in order to respect everyone’s time.
  3. Record the outcomes. If you don’t have clear outcomes from a meeting, then it shouldn’t have taken place. Writing down the outcomes saves everyone time in the long run as they can refer back to the notes, and there is a clear documentation of everyone’s next steps.

In my business (Harpoon), there are two other owners that I meet with regularly. We keep a running agenda document updated throughout the week for items we need to discuss with each other. When the meeting starts, we hit the first item on that list. On the same sheet, we record the outcomes of things discussed. We use Basecamp documents for this, but you could easily use Google Documents or Evernote to achieve the same collaboration.

We didn’t always have this system down, it took a few weeks of meetings that went way too long and were too off-focus, even though the three of us value smaller meetings. The discipline of writing out that agenda has made a huge difference for us, and fewer things slip through the cracks.

Don’t get tripped up on the habit of letting meetings grow a mind of their own. Keep them short, succinct, and purpose-driven.

3. Waiting Until Everything is Perfect

Waiting for Perfection

Being a perfectionist is a wonderful trait that ensures that what you accomplish is high-quality. Sadly, it is the perfectionist nature that ensures that those tasks you accomplish are few and far between.

I often meet couples who are in love, who want to spend the rest of their lives together, but don’t want to get married until they have their financial lives in order. As someone who has been married for 13 years, I can assure you, there is nothing you can do to be fully ready for the joys and challenges of marriage. The same can be true of having children (I’ve had four), and launching a product.

Things are rarely going to be so perfect that you have no other choice but to launch. Whether it is launching that product itself, an advertising campaign, or the next phase. When you jump in with both feet, you find a way to make it work, and if it isn’t working, you have great motivation to make it so.

A great piece of advice I heard from another blogger is to write out the titles of a few blog posts, then schedule them to go live (even without writing the actual post). The motivation then is to ensure that the post doesn’t go out with simply a headline, so he makes darn sure to jump into his platform every week to write new content.

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When building Harpoon, we had a lot more features planned out than the ones we eventually launched with. We had to decide which features were essential to launching and cut out the rest. One of these features was support for international currency. We decided to launch only supporting the US dollar. Within the first round of invites that we sent to our early-access list, we received a significant number of requests for…you guessed it…international currency support.

Seeing that our customers were now waiting on us to deliver lit a fire that caused us to build out that feature in record time. In fact, we had it in the application before we exhausted all of our early-access invites so it was ready when people logged in for the first time.

If we would have waiting to launch until we had international currency support we would have taken 2-3 times longer to implement it, since there was no real motivation for getting it out faster. Also, we looked really good to our customers when they saw how responsive we were to listening to their feedback, and it caused many to become vocal fans of our product.

Don’t get tripped up on waiting until everything is perfect. Jump on in, you learn the fastest when the motivation to get something right is the strongest.

4. Bottlenecking the Processes


When I was a consultant, I had lunch with an entrepreneur who was looking to hire me as a developer. As she was trying to explain what it is she needed, she was very vague and I had a hard time interpreting exactly what she was asking. Finally I simply asked her “Can you just tell me what your product needs to do, and I’ll help you determine the best approach to getting there.”

What happened next floored me, she told me “no”. She was actually unwilling to tell me what her application would do, even though it wasn’t even built yet, because she “hasn’t told anybody” yet, and isn’t ready to share the idea with the world.

The meeting ended awkwardly as I explained that this project wouldn’t be a good fit for me. In truth, I also knew that her fear and need for control would be a huge bottleneck to the entire project.

I’ve worked with entrepreneurs that want to approve every step of the process, and because they are so busy, end up holding everyone else up in the process. Yes, there are times when an entrepreneur needs to give approval, but the most progress is made when there are others empowered to make decisions and move the ball forward.

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I recall from Tim Ferriss’ book The Four Hour Workweek that a pivotal moment in his passive income stream was enabling his customer support personnel to solve any problems costing less than $100 without needing approval from him. Issues were solved much faster, Tim was bothered much less, and the employees felt empowered to do their jobs. It was a win all around.

Don’t get tripped up thinking that you have to control the whole process. Trusting other people to help you find success will open you up to the expertise of others, and your business will grow larger and faster than if you really were the only one pulling the strings.

5. Being Reactive Instead of Proactive

Reactive instead of proactive

When a customer has an issue, we react in order to find a solution. When we run out of money, we react and find ways to stay in the black. Being reactive is automatic, it’s natural, but it causes a lot of stress.

Unfortunately, because being reactive is our default mode as people, it holds us back from a less stressful, more successful business. In contrast, being proactive gives us a piece of mind in knowing that our bases are covered before any real urgency arises.

As an entrepreneur, being proactive means planning out the future, creating contingency plans, and being well-aware of potential pitfalls moving forward. A proactive entrepreneur spends money on a lawyer at the start of their business to ensure they have their legal affairs in order, whereas a reactive entrepreneur spends even more money on a lawyer when they are later sued because they didn’t perform their due diligence.

There is definitely a place for reaction, it cannot be avoided. In fact, being reactive is good in cases where you accidentally discover a profitable avenue that you didn’t know existed. This type of reaction is known as being “agile”, and it can be a big advantage to entrepreneurs as opposed to big businesses.

To be a proactive entrepreneur, time must be scheduled to reflect on the past, and make concrete plans for the future. This is both on a micro and macro level. For example, it is important to have a plan for the next year, but it is also important to have a plan for the next 8 hours when you start your workday.

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If you are letting emails, unscheduled phone calls, or random YouTube videos suck you away from accomplishing your goals for the day, you are allowing your reactive nature to take over. In contrast, if you have a plan for the day, and ignore distractions that come along throughout the day, then you will reach your success milestones quickly and reliably.

Don’t get tripped up on the habit of being reactive instead of proactive. Spending time up-front to plan out strategy and contingency plans lead to a less stressful lifestyle as an entrepreneur, and one that is often much more successful.

About the author

Ryan Battles

HI, I'M RYAN. I believe the best way to learn and remember is by writing things down and sharing them with others. This blog exists to help me synthesize and process my journey towards self-improvement.

Ryan Battles Data-Driven Marketing Specialist

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About me

HI, I'M RYAN. I believe the best way to learn and remember is by writing things down and sharing them with others. This blog exists to help me synthesize and process my journey towards self-improvement.