Small Biz Advice: Gauging When You’re Ready to Grow



Dear Holly,

I make leather goods and sell them on my e-commerce shop as well as the markets around Brooklyn.  

I’ve had some success so far, and people like my product. I’ve been doing the markets for about two years now and feel like in a lot of ways, I’m not growing. But, I also feel totally overwhelmed about taking the next step and turning this into a bigger business.  

There are stores that I would love to have carry my product, but I know that means I’d need a bigger team to produce the product, and I’d need to do some serious planning.  

Do you have any advice on what I need to consider before I make the leap to grow? I’m not sure if it’s the right decision for me, and I can’t decide how to proceed.


One Toe In

Dear One Toe In,

Thanks for this brilliant question. I bet many of the other vendors you see in markets face this issue as well. It’s great that you’re actually admitting that it scares you versus pretending to be cool with it and doing something that doesn’t feel right. That always leads to disaster.

I work with a lot of clients who are comfortable as a one-man-show, and the thought of bringing on team members and expanding really scares them. The good news is that there are a few questions you can ask yourself to get a better understanding if growing is the right path for you.

The first question I would ask is what is the long-term vision of your business? Though you can certainly start a business without a plan or knowing exactly where you’re going, there comes a time when you must step back and decide where you’re headed. Now is that time for you. Have you thought about where you see your business in 5 to 10 years? If you look 5 years into the future and you don’t see bigger stores carrying your product, employing a team to help you expand, or yourself as a leader, then it’s probably not in your best interest to head in that direction now. Visioning can be a very challenging step because often times, business owners start with a product, and thinking about committing to a long term vision freaks them out. It’s a completely different way of working. Don’t force yourself to determine your vision today; it often takes weeks or months to answer. Sit with it for a while and see what comes to mind.

The second question you need to ask yourself is how willing are you to learn new skills and be really uncomfortable? See, the thing about growing a business is that it will force you to become a better leader, a better manager, a better marketer, etc., and if those aren’t skills that naturally come to you, it’s likely going to push you out of your comfort zone to acquire and master them. All successful business owners go through this phase. Willingness to be uncomfortable and learn new skills is a must if you want to grow a business. If you’re not OK with that and would rather stay in your comfort zone, then don’t expand your business!

Finally, ask yourself how committed you feel to seeing this business through down times, risky deals, rejection, and challenges. Do you believe in what you’re doing enough to stand by your vision during those times, or would you rather avoid those types of situations? Growing a business means you must go all in and commit. It means you can’t just stand on the side and dip your toe into the pool, you must go all the way and take the plunge! If that type of commitment scares you, reconsider the idea of growing. If it excites you, then by all means go for it!

Most importantly take your time deciding! It seems like everywhere we turn, we are inundated with the message of rapid growth. Do what’s right for you. Take your time and give these questions the consideration they require. How you answer these questions will affect the next 5 to 10 years of your life, so don’t rush your decision. Only you know what’s best for you.

Good luck!

Holly Howard runs Ask Holly How, a small business consulting company based out of Williamsburg, Brooklyn that works with a wide variety of businesses from restaurants to retail to art studios and pretty much everything in between. Her clients report increased income and profit, decreased expenses and a significantly better quality of life. Holly heads up the Small Business Book Club at McNally Jackson Books.

Want valuable insight into how to grow your business? Holly hosts free 30 minute strategy sessions at The Yard in Williamsburg. Email her to set up a time or to ask a question for the next Ask Holly How.

And starting Oct. 30, Holly is applying her knowledge and experience in the restaurant industry to a special, four-part course, “How to Open a Restaurant,” that she’ll be teaching at The Yard with guest lecturers from local restaurants like Carolyn Bane, chef and co-owner of Pies ‘n’ Thighs, and Andy Rosenberg, Director of Marketing at The Meatball Shop. Sign up for one or all four sessions, and you’ll get advice on business planning, operations, sourcing a menu, marketing and more. Tickets are $70 per session or $208 for the entire program when you use the 20% discount code, bkbased.

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