Five Reasons Why Starting A Business Never Gets Easier (And Why That Shouldn’t Stop You)

Louise Hendon has founded five D2C brands and is now the CEO of Doggie Karma, a company that provides natural supplements for dogs.

I just started my fifth and sixth businesses a few months ago. And in my many moments of despair, I would repeat, “Why, why, why?” to myself as I cradled my head. In my moments of elation, I would tell myself that this is what I love doing, it’s what I’m great at and this is my destiny. And in the hours in between, I try to stick to the plan and keep plodding on one step at a time.

I truly believed that this time, starting a business would be different. I wasn’t a novice anymore. After all, I had started four profitable businesses in the past and sold three of them. I had also decided I was going to be more deliberate in creating a successful business. I wrote a business plan, hired two business coaches, ran my ideas by colleagues I respected and even wrote out quarterly goals well ahead of time. And to top it all, I didn’t need to raise money, as I had just successfully exited two previous companies.

Everything seemed to signal success, so why do so many days of this entrepreneurship thing still feel like such a struggle? Here are five reasons I came up with after months of frustration.

1. It’s inevitable that you will make new mistakes.

I told anyone who would listen that I wanted to make new mistakes with my new businesses. But when I did make new mistakes (like hiring too much too soon), it still felt just as painful. And platitudes about having learned a “valuable lesson” from well-meaning friends only made me feel worse.

Luckily, I have two great business coaches who helped me realize that millions of entrepreneurs have trodden this same path before me, and making new mistakes is part of the growth process. Having mentors, partners, coaches and friends who have gone down this path before is essential to helping you recover quickly from mistakes or avoid them altogether.

2. Repeating old mistakes is also inevitable.

My goal with these new businesses had been to avoid making the same mistakes I had made before. But guess what? I broke that goal even with my initial business plan. I’ve counseled countless business owners about the dangers of focusing too much on social media at the beginning stages of a company, as I’ve found it’s a slow-growth model that is not “free” when you consider the time and effort that goes into creating content. Yet, I started my new e-commerce business by pouring tens of thousands of dollars into building up our organic social channels.

Repeating old mistakes is often a sign that something wasn’t properly understood, so I went and journaled about business models and situations in which social media would (and wouldn’t) be highly beneficial. You can try doing the same. Journaling is a great way to process errors and learn more deeply from them.

3. Losing focus is a constant problem.

Shiny object syndrome is real, and it affects pretty much every entrepreneur I’ve met. When I’m feeling down, I call this syndrome “ineffective greed,” and on better days, I dub it “boredom.” Whatever you choose to call it, and however you might choose to excuse it, the simple fact is that it can detract you from your main goal: creating a successful business.

The best way to focus is to plan ahead. Then, keep adjusting and reviewing the plan so you can prioritize taking action each day on the steps that will bring the biggest leaps forward.

4. Every business is different and has its own unique challenges.

After reading Tim Grover’s book “Winning: The Unforgiving Race to Greatness,” I saw similarities between business and sports. For example, while the over-arching rules of basketball do not change from game to game, the players on the court, the audience watching and the stakes involved change every single time. The same goes for businesses.

Even though I started another e-commerce company and planned to use similar marketing strategies in my new business, I quickly realized that this new business had different challenges. Even if you’re an experienced entrepreneur, when you’re starting a new business, keep in mind that your audience might be different than your past companies, so you will need to dive deep into that community to better understand their needs and behaviors.

5. The marketing and business spheres are evolving faster and faster.

I built my previous companies on Facebook advertising, but that landscape has changed dramatically. That’s why I’m building my new e-commerce brand on TikTok advertising instead. While you could get away with product image ads and heavily branded videos on Facebook, the new platforms your audience is using are also important to explore. TikTok, for instance, forces advertisers to do better. Not only do you have to squeeze your entire message into about a minute, but you’ve also got to make it compelling to watch while not being too over-produced.

It’s taken me seven months to figure out all the different TikTok advertising strategies, and there’s no guarantee it will remain lucrative for long. However, the business and marketing spheres evolve fast, and there’s no time to be complacent in entrepreneurship. Ensure you’re willing to learn, test and pivot faster and faster.

Keep going, despite the struggles.

I could list more reasons why starting a business never gets any easier, but the truth is that entrepreneurship doesn’t have a three-step guide for success. Being an entrepreneur is about waking up every day and believing all over again. It’s about seeing possibilities even when life seems to beat you down. But most of all, it’s about sharing — sharing your knowledge, sharing your creations and sharing your successes as well as your failures.

To me, that’s what makes this journey worthwhile, and it’s why I keep doing it even though it never gets easier.


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