Open Forum: What's the Toughest Challenge You’ve Faced as an Entrepreneur?

Open Forum: What's the Toughest Challenge You’ve Faced as an Entrepreneur?

Hardest challenge for entrepreneurs.On Shopify’s social media accounts, we’re always asking merchants and readers questions about their entrepreneurial journey. This week, we asked you:


We received a number of thoughtful replies, and we wanted to keep the conversation going. To begin, let’s start with breaking down the challenges listed in the poll.

1. “Finances aren’t endless.”

A common adage in business is that it takes money to make money. Access to funds and capital certainly helps, but completely buying into clichés and pithy sayings is an easy way to give yourself permission to never get started.

The cost of starting a business is coming down all the time. Now, more than ever before, there exist workarounds and makeshift ways to test the market with a new product idea long before you’re forced to make a risky, irreversible investment. Of course, that doesn’t make access to additional funds any easier, but it does give you options to validate a business while keeping operational costs lean.

Just as important as direct access to funds is the ability to address self-limiting beliefs about money. Shiny-object syndrome, for example, is often the worst form of entrepreneurial procrastination; it can cost you cold-hard cash and wasted time. Here are my principles for staying financially focused:

  • Don’t get ahead of where you are. New businesses don’t need to plan that far ahead. They need to #GSD today. Only after you’ve survived the initial gauntlet and have confirmed you’re selling things people want to buy should you bother with long-term planning.
  • Don’t let trivial purchases become a bottleneck. That thing you think you need? You don’t need it. Stop spending time and money on frivolous distractions and unearned pampering; that new shipment of lush business cards won’t determine your fate, I promise.
  • Own your finances to own your future. We’ve written before that while your accountant can be a trusted adviser, they aren’t your CFO. You are ultimately responsible for the financial decisions you make, and that requires basic levels of financial literacy and discipline.

Learn more with these articles:

2. “Knowing when to adjust.”

Though he was primarily speaking to software companies, Marc Andreessen has written that, “In a great market—a market with lots of real potential customers—the market pulls product out of the startup.”

Every new business faces an uphill battle when making their first few sales, but what Andreessen is talking about here is that a healthy market comes bundled with pre-existing demand; you should be convincing customers to buy your product, not to buy the problem. This means your company’s value proposition should speak to things people already want, or want to do.

When faced with too much resistance you have to consider whether your product is what people actually want, or whether your marketing is saying what people actually want to hear. It might be the product or it might be how it’s positioned, but finding solutions to both problems starts with the market in mind.

And if things aren’t working out at all, you may have to make the arduous decision to either close up shop or potentially sell your business to someone else. Both options loom over most founders, but the silver lining is that pruning away what isn’t working makes room for new opportunities.

Learn more with these articles:

3. “Goodbye social life.”

Work/life balance is an admirable pursuit, but the demands of entrepreneurship often require founders to pursue work/life harmony as they slowly march their way up the proverbial mountain.

Harmony means work fits and adjusts, as best it can, to the confines of the life you want to live. It’s less about the zero-sum game of finding perfect balance, and more about feeling good about how you’re spending your time, regardless of the ratios between “work” and “life.”

You can find harmony even when you’re making sacrifices (and even when “balance” is just a pipe dream). But it’s unquestionably healthy and highly encouraged that you take stock of your time, and make sure the pace you’re moving at now will lead to positive, productive results in the long-term.

"When you're at work, work. When you're at play, play. Don't play at work and don't work when you should be playing. Train yourself to give all your focus to the goal." —David Cancel, CEO of Drift

Sometimes you need a vacation, other times you just need “me time” away from your business. Harmony means not feeling guilty about pursuing either, so long as you understand where they fit within the life you’re trying to live.

Learn more with these articles:

Self-care for entrepreneurs.

4. “Hiring is tricky.”

Regardless of whether or not you’re handmaking your products, businesses are handmade by the founders who started them. Because of this, it can be emotionally challenging to bring in new people to help keep the ship afloat, especially if you’ve never led a team before.

Anxiety begins to creep in the moment you entertain the idea of working with someone else: “Will they care about the business as much as I do? Will they sweat the details? Will customers notice (or mind) that I’m not handling everything anymore?” These questions extend to doing right by your new hire: “Will I be a good, positive leader? Will I be able to set this person up for success now and in the future?”

I always try to remind entrepreneurs that temporary or contract help can be a fantastic first step toward “firing yourself” from work you shouldn’t be doing, without having to make a full-time hire. Working with freelancers is a process unto itself, but it’s much easier to course correct when you’re working with an expert on a part-time basis.

Whether you’re prepping for a product launch, planning a new marketing campaign, or you just feel like you’re up against the wall while handling the holiday rush, there are opportunities to test and benefit from having an extra set of hands available, and long before making a full-time hire.

Learn more with these articles:

What unforeseen challenges have you faced?

Too often, the places you go to learn can feel like a one-way conversation. That might include the very blog you’re reading now.

We love sourcing the best advice we can find on starting, growing, and scaling a profitable online store. While each entrepreneurial journey is altogether unique, business owners share many of the same struggles. Sometimes the best way to get advice is to simply share what aspects you've found to be challenging with a community of people who can relate.

💬 So we'd like to continue the conversation that began with our Twitter poll: What's the most challenging thing you've encountered since starting a business?

About the Author

Gregory Ciotti is a writer, marketer, and lead for Shopify's Ecommerce and Retail publications. He's always on the lookout for uncommonly good stories and advice. Get more from Greg on LinkedIn.

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