The 7 Hardest Things About Being an Entrepreneur That You Never Expected

There are certain traits that define an individual’s propensity for entrepreneurship. They’re hugely resilient, they’re awesome at networking, they’re great communicators, and they have the unwavering confidence that they will eventually be successful if they just keep going.

Whether you were born to start your own business or are determined to learn the entrepreneurial ropes, there are a lot of unexpected challenges that even the most experienced entrepreneurs couldn’t have anticipated when they first started.

I was fortunate enough to have been born into a hard-working family, which allowed me to be more vigilant about the pitfalls that typically come your way as you start and grow a business. My journey through entrepreneurship wasn’t easy or simple, but I can truly say that the challenges I didn’t expect (those that came out of left-field) were the ones that were the hardest to address.

With decades of experience and over 20 successful businesses to my name, this is the most useful tip I can give to aspiring entrepreneurs: anticipate these unexpected challenges before they happen.

StartupNation exclusive discounts and savings on Dell products and accessories: Learn more here

Don’t let the following catch you off guard

Training and delegating

Entrepreneurs build their businesses from the ground up—so it’s very likely that you have a lot more than just money invested in your business venture. You’ve dedicated a lot of time to growing your company, which means you’re emotionally invested in it. While that’s a good thing, it also makes it very hard to delegate tasks.

But it’s faster if I just do it myself!”

True. But before you know it, you’re piling too much on your plate. You’re unable to get things done efficiently; you’re rushing to get things done, missing deadlines, constantly making mistakes, and end up feeling burnt out.

It’s very hard to entrust a business that you’ve poured your heart and soul into, into someone else’s hands. But it’s something you must learn to do if you want your business to survive the early stages, grow and thrive.

I always say, delegate or stay small. If you feed them for a day, you’ll end up feeding them forever; or teach them to fish and they will feed themselves.

So, even if it seems like it will take you three times longer to train a team member to complete a task, versus just picking up the slack yourself, your team has to learn.

And as your business grows, you’ll see this investment pay off.

Related: 10 Valuable Lessons Every Entrepreneur Must Learn

Leverage your strength

You’ll wear many hats as an entrepreneur. Resist the urge to be the jack of all trades, master of none. Learn your strengths, focus on them and develop them.

Entrepreneurs are usually skilled in one or two of the pillars within a typical business plan. That’s already a huge advantage unto itself. Instead of focusing on the things that you cannot do, put your energy on the things that you can do. That will contribute a lot more to your business’ growth. Then, as we just covered, delegate the rest.

Have the conversations that matter

Having that difficult conversation now is better than brushing things under the rug in the interest of maintaining the peace or not ruffling any feathers. This goes for every aspect of running a business—from an employee’s poor performance to a supplier not meeting your standards.

Have those awkward conversations early and often. If your arm is infected, cut it off before it infects the rest of your body. I know it’s hard to let off a tenured team member who has not been performing, but look at the bigger picture—how will it affect your team and your company’s long-term goals if you allow it to continue?

Scale for success

The team that you start out with may not be the team that leads you to the fourth and fifth iteration of your business plan.

Does that seem like a hard pill to swallow? It is, definitely. Loyal and dedicated team members are hard to come by, but a loyal and dedicated employee who can’t get the work done will be an albatross for your high performing team members.

Perhaps these individuals don’t have the skill sets needed to effectively scale your company, or maybe they need additional training and knowledge to reach your new goals.

Whatever the case, approach your growth realistically—know that that while loyalty is important, there will be instances where you need to make a change for the long-term health of your business.

Pay yourself first

This is probably the opposite of what every other entrepreneur would advise. Common entrepreneurial knowledge says that you have to put everything back into your company in order to grow it to the next level.

However, I disagree. When you start gaining good financial footing, you have to pay yourself first. Otherwise, you won’t remain motivated to keep going. 


Time is finite. It’s limited and for a lot of entrepreneurs, time is truly money—make sure you treat it accordingly.

Time is the only thing we can’t get back or make more of. So, plan your days and don’t be careless with your time. Get your victories early in the day, and map out your days, hours and minutes.

Sign Up: Receive the StartupNation newsletter!

Get out of the weeds

It’s hard not to get immersed in the day-to-day complexities of a running business. Focusing on the details are important, no doubt, but it can be very overwhelming. Therefore, don’t let yourself get bogged down by all the details. Make time to stop and breathe before you continue ticking things off of your to-do list. Remember to keep your big picture goals in mind.


A well networked entrepreneur is an asset, and you’re only as good as the five people you spend most of your time with. Build your network, but be selective of the company you keep. These are the individuals you will learn the most from, who will be your sounding board, and who will give you advice. Surrounding yourself with the right people matters more than you think.

These are the challenges that I wish I knew to expect when I started my entrepreneurial journey. If you’re just starting yours, I hope this advice will serve you well.

Leave a Reply
Related Posts