How to Run a Business When It’s Not Going According to Plan

Lindsay Mound/Thrillist

So you've made that business idea of yours into a business reality. Maybe it’s the radical reinvention of the spa experience that's transforming your neighborhood, or a new snack that’s flying off the shelves in Whole Foods. Or maybe you struck out on your own and opened your own company or studio or khlav kalash cart. Whatever passion you’re now calling your profession, just know that things will never go according to plan. So while you may have done everything right thus far, be wary of when the road inevitably takes a left turn. Here are the principles to get you through the growing pains courtesy of the dreamers-turned-doers who successfully tiptoed through the ownership landmines. See if your managerial style could use their advice below.

Lindsay Mound/Thrillist

There are no rewards without risks

From an East Village apartment to some of the finest jewelry shops in the world, Janie Kruse Garnett Fine Jewelry is wooing the world one finger at a time. When Garnett, a self-trained designer, started out, she learned some industries aren’t kind to the upstarts. They’re dominated by the old guard, professional success based on some opaque combination of experience and exclusivity.

Garnett, an independent jewelry and luxury goods designer based in New York, saw those barriers to entry in her own trade and decided to bust them down at full speed – but first she had to make the conscious decision to separate her professional personality from her personal behavior.

“It was hard to question the very questionable pricing of two 65-year-old dudes from Long Island when you are a very polite 25-year-old girl from the suburbs,” says Garnett. "Take the ball and run. Business isn’t a dinner party, people aren’t going to be aghast when you ask them to explain where they got their numbers from.”

Garnett also had to train herself to banish what looms largest in the back of every entrepreneur's mind: fear of failure.

“I was so scared that ‘The World’ might see that I hadn't succeeded that I didn't even try a bunch of very rudimentary things,” she says. “My resolution for 2017 was to seek failure, and the risks I've taken have paid off in such surprising, and wonderfully rewarding ways.”  

Lesson learned: failure isn’t the worst thing in the world. It can change your MO and lead you to new lessons and bigger rewards. Garnett calculated the amount of failure her business could tolerate and invested her resources in risks that would pay off whether they hit their primary objective or not. When she wanted to take a shot at designing high quality silk scarves, she knew that she’d face stiff competition from fashion houses that have defined the industry for decades, if not centuries.

“With scarves, Hermes is it. Full stop,” she says. “I was so certain I would be laughed off the field, but I had been thinking for years that there needed to be a slightly less serious luxury brand out there.” Garnett made her move, and in the process learned that there’s always room for the brave ones. “Just because there's already a beacon of what's ‘right’ doesn't mean there isn't another ‘right’ out there. People aren't going to run after you with pitchforks.”

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You can do anything...but have to do everything

“There’s nothing out of scope as an owner,” says Nora O’Malley who, along with her business partner and friend Phoebe Connell, started the deliciously well-designed cracker company Aida as well as the East Village wine hotspot Lois. “It’s your business so you need to know how to do everything. At the end of the day you’re watching your own back and you’ll serve yourself better by being aware.”

Learning those lessons quickly can also be the difference between a successful venture and one that sputters out after the initial energy is spent. When O’Malley and Connell opened Lois, they had both spent years working in restaurants and bars so they knew the lay of the land better than most. Not so with Aida, the cracker company.

“Neither of us had ever started a [consumer packaged good] before, so there were a ton of things we had to learn on the fly,” Connell says. The duo got to know the CPG arena quickly, and the quick uptake has been a key ingredient to their success. “I now know so much more about plastic bags than I ever thought possible. And who knew barcodes were so expensive?”

The boss doesn’t -- and probably shouldn’t -- have to be the best at every stage of production, but the more you understand about each level’s function, the more you’ll be able to plan for its needs and schedules. Plus, employees will respect you if you’re able to put on an apron and get into the grease next to them in a pinch. A boss who gives orders is a manager, but a boss who is willing to do anything in service of the common objective... that’s a leader.

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Produce or perish

Patience can seem a long forgotten virtue in today’s business world but, according to Cam Curran and Phil Tortoroli, co-founders of the Brooklyn record label Styles Upon Styles, it’s been a major key to their success in a crowded industry. “My advice? Stay consistent and plan to stick around for a while,” Curran says. “I’m talking decades, not years -- because as soon as you take a year off or shutter the operation altogether, no one is really going to care that you're gone.”

That rise-and-grind mentality has led to a sustained run of triumphs for the upstart label including the discovery and cultivation of artists like Denitia Odigie, Vorhees, Rosehardt, and Gabriel Garzón-Montano. But entrepreneurs looking to mimic the label’s success will have to match the duo’s considerable energy to plan, produce, and repeat.

“In our industry, people only ever remember what you've done lately,” Curran says. “So if you're jumping in without a plan for the future or the resolution to keep it up or an actual passion for releasing records with all the tedium that entails -- just really think it through before you commit.”

The first takeaway is that the product doesn’t have to be perfect, it just has to be as good as it can be; it’s more important to put out something you’re proud of, on time and a regular schedule. The other takeaway is that to do that, you’re going to have to do a lot of mule work. But even that can pay off big: not only is it getting your work to completion, you may just lull your brain into big ideas for what’s next. Nothing inspires work like work, especially when you’re exploring the nuances of your skills, tools, and process.

You never stop learning, but you set your own syllabus

By now you know that being your own boss isn’t all trashed alarm clocks and unlimited summer Fridays. When the business is linked to just a couple people’s work, your personal reputation rides shotgun to your professional one so you’d better know what the hell you’re talking about.

“Everything our firm produces has our names attached to it,” says Ashley Bigham, the co-founder of Ann Arbor-based architecture firm Outpost Office along with her husband Erik Hermann. “Architecture is a small discipline and we aim to contribute to it through our design work. Putting our names on something, even an Instagram post, means something.”

Personal investment in every venture is its own kind of reward, though, and the Yale-educated architects have embraced independence with gusto by vacuuming up as much industry knowledge as humanly possible.

“Right now, we are definitely in the ‘all knowledge is good knowledge’ camp,” Bigham says. “You never know when that knowledge can feed into a new project. We often test materials, colors, or fabrication techniques which we end up using on completely different projects. Right now we look at every fail as a future success.”

The duo’s try-and-try-again attitude has been central to their maturing firm’s philosophy and can be applied to everything from startups to artists. The Beckett line “Fail again. Fail better.” isn’t emblazoned on the walls of a thousand Silicon Valley companies for nothing.

Grinding has also led Bigham and Hermann to explore the more philosophical corners of their discipline, a path uncovered after conducting deep research for potential clients. “We just started our podcast, Site Visit,” Hermann says. “And we did this because we wanted to have more conversations about architecture with more people and want the world of architecture to be more accessible to everyone, not just design professionals.”

Bigham and Hermann’s best advice? Bust your butt and never stop absorbing knowledge, especially from the successful people in your field.

“Find someone a few years ahead of you in the field who you admire and study their success. What moves did they make to get where they are? What were they doing 5 years ago?” Bigham says. But most important of all: “Never stop working. Hustle and fake it. If you don't have something to do, invent a project.”