You Will Survive: 8 Strategies to Overcome New Entrepreneur Anxiety

You Will Survive: 8 Strategies to Overcome New Entrepreneur Anxiety

Close your eyes and imagine stepping onstage to deliver your first TED Talk. It’s one of the most important moments of your career… only you forgot your pants.

Feel that weight in your stomach? Good. That same wide-eyed, what have I done? nightmarish dread creeps over every entrepreneur soon after the euphoria of escaping the 9-to-5 world wears off.

This panic arrives the moment we realize we’ve strayed too far from the paycheck mothership and feel compelled to run back to the salaried womb. Congratulations! The act of starting a business demands this initiation from every entrepreneur. It feels awful, but it’s perfectly survivable.

Breathe and know that there’s no need to retreat back to cubicle-land. No, you did not quit your job too soon.

Your anxiety isn’t entirely uncalled for. Day 1 of being your own boss is pure bliss, but as the months pass you’ll likely watch your bank balance dwindle and notice your zest fizzle to a cool reluctance. One day you realize that you don’t have the financial runway or the grit you thought you did. This is normal.

You’ll tumble down Maslow’s hierarchy of needs, hitting every rung on the way down, waking dazed on the security tier floor. In this Monopoly jail, you’ll have plenty of time to ruminate on where it all went wrong, but these eight practices will pull you through the panic and help you keep a steady hand on the wheel of your business.

You Will Survive: 8 Strategies to Overcome New Entrepreneur Anxiety

1. Secure a “consulting” gig.

There is an escape from the Money Panic, and it doesn’t involve selling off retirement investments or increasing your credit card limit. You need a consulting gig that will help cover monthly bills. This doesn’t have to mean putting on a tie and helping corporations “find efficiencies”—it could be a simple bartending job three nights a week or a few hours driving for Uber, maybe even helping your old company by keeping some of your old duties on a contract basis.

When you find a consulting gig—consistent part-time hours with an hourly rate—you’ll have peace of mind knowing there’s enough money coming in to replenish your shrinking coffers. Having your security needs met is a vaccination against the Money Panic, and it allows you to focus on the real work of building your business.

2. Cut expenses to the bone.

There is a quote that goes something like, “Entrepreneurship is living a few years of your life like most people won’t, so that you can spend the rest of your life like most people can’t.”

Most new entrepreneurs focus on that last part when deciding to jettison the 9-to-5 job, but don’t spend much time pondering what, exactly “living like most people won’t” entails. “Sure, it’ll be tough, but I’m tougher!” they say.

But are you willing to let those few lean years turn into five or 10? The Universe often laughs at your expected timelines. To take a new company to profitability requires a herculean effort, day in and day out, for much longer than you might hope.

You can’t expect to live the lifestyle you had while under the protection of a payday every two weeks. Your part-time consulting job likely won’t cover all the bills, so you may need to cut the fat from your household budget. That may mean canceling your Audible membership, exercising at home instead of the fancy gym or shopping at the budget supermarket instead of Whole Foods.

When Elon Musk was building the precursor to PayPal, he slept on his office couch instead of renting an apartment; now he’s a billionaire. If he can sacrifice, you can, too.

3. Shelve strategy, prioritize cash flow.

As an entrepreneur, your superpower is vision; you see an opportunity to change the world that nobody else is acting on. But someone needs to go out and sell. The entrepreneur’s greatest strength is also a weakness. Big-picture thinking advances civilization, but it’s the daily yeoman’s work that turns vision into reality. The temptation to focus purely on business building will be great—perfecting the product, upgrading the website, tweaking marketing copy—but none of this pays the bills like sales.

When the 2008 financial crisis hit, Tel Ganesan, founder of IT and software company Kyyba Inc., wrote out “a simple index card with ‘$$$$’ written on it” that reminded him to prioritize cash flow. “To this day, that index card is kept in the same spot in my office, even through various office moves,” he says.

Cash flow is the lifeblood of every business. If it dries up, the body dies. By all means, create your business plan canvas before you leap from your 9-to-5. But now it’s time to get into the sales trenches, and prioritize money in the door, even if that’s not as sexy as adding another feature to your app.

4. Lower your expectations.

We revere successful entrepreneurs because they seem to have unlimited capabilities. When we set out on our own business journey, we’ve already bought into the myth that we can do it all. What we forget is that Richard Branson’s portfolio of planes, trains, spacecraft, electronics, charities, radio, and on and on started with a single record store. He didn’t try to do it all—not at first.

Are you trying to build the app and website, grow seven social media accounts, host webinars, talk to customers, sell, and secure venture capital all at the same time while also juggling a personal life? Cut it out.

If your cash flow projections show you making $1 million in the first year, or tripling sales this quarter, or hiring 100 new employees, your expectations may need to be rightsized. Ambition is laudable, but not when it crosses the border into Fantasyland.

You Will Survive: 8 Strategies to Overcome New Entrepreneur Anxiety

Stop doing “everything” OK-ish: Choose a vital few areas where you can deliver exceptional results. Setting realistic expectations is not equal to selling yourself short; it’s what adults do. And when your capacity grows, so can your ambition.

5. Take a vacation.

In the salaried world we get at least a couple weeks’ paid vacation and feel justified disconnecting from work. Why is it hard for entrepreneurs to unplug? Because your business doesn’t work unless you do in the early going. When you hang your own shingle, you may find yourself on call every waking hour. But running your body and mind at the redline leads to burnout. You are the company. If you collapse, so does the shingle.

It’s counterintuitive, but when you start thinking, I’m not cut out for this! and feel like tucking tail back to the old J.O.B., it’s time for a vacation. Resist the urge to work harder—your efforts will flop while you’re depleted.

When COVID hit, CEO of TeamBuilding Michael Alexis watched yearly revenue plummet from $2.8 million to zero overnight. Rather than work longer hours, he took his partner to climb a mountain. “Cold, sweaty and full of doubt, I remember thinking, Our business is failing,” he says. But by the time he got back down the mountain he knew how to pivot quickly, and within one year the company had thousands of clients under the new business model.

A vacation need not mean a flight to exotic destinations: Book a secluded Airbnb for a couple of nights or have a staycation. Just shelve the work and prioritize getting your head back on straight.

6. Be a pro, not an amateur.

When you are employed, you are by nature a professional. You don’t really have the option not to clock in on Monday morning. But when you no longer have a boss to answer to, there will be great temptation to sleep in or take a two-hour lunch. This is the mentality of the amateur.

Author Steven Pressfield describes a force called Resistance that keeps you from doing what needs to be done, especially in creative pursuits. Amateurs succumb to Resistance often, calling up excuses like, “I don’t feel like working today, let’s hit the beach.” But professionals slay the dragon of Resistance each day, making client calls or sitting down to paint even when the spirit doesn’t move them, because that’s the job.

7. Harness self-doubt.

Any entrepreneur can tell you that the hardest part of the role is managing your own mental state. By leaving the 9-to-5 nest, we launch ourselves into the unknown and multiply our challenges. “Expanding your sphere of comfort and abilities comes with a cost: repeated self-doubt,” says author Tim Ferriss.

Self-doubt is an unavoidable side-effect of striving to be ever-more awesome, but we can choose to let it cripple us or harness it. You can change the story that you’re telling yourself about what these fears mean: Have you made a huge mistake? Or is this doubt an expected emotional reaction?

Your worst-case scenario fears may seem real, but feelings are not facts; they are passing clouds that you can simply observe as they float past on their own. Once you realize this, you start to harness self-doubt. It can act as a check on your flawed assumptions, a motivator to work harder or a prod to reach out to mentors and allies for advice.

To practice, use psychological distancing, which Alicia Nortje, Ph.D., describes as a “technique where we step away from a situation or position so that we can gain perspective.” This might mean leaving your work environment (that Airbnb getaway is looking better and better), or even speaking about yourself in the third person.

When you accept self-doubt as a part of the path, it ceases to weaken you and starts to propel you forward.

8. Rebuild your relationships.

You may not be blood brothers with your former co-workers, but daily social interaction with other adults is a valuable benefit provided by the workplace. Humans evolved to need the tribe to thrive, and when you leave the traditional work world, you are cut off from this social network.

“Entrepreneurship of any kind can be extremely lonely at times—as well as terrifying and overwhelming,” says Black Ink Coffee owner Parker Russell, and this proved doubly true in COVID times. But when you find a network of like-minded people, “You can share your struggles, pick up gems of advice and, ultimately, grow,” Russell says.

No entrepreneur can build a business alone, and collaboration is the quickest route to growth. Mentorship can help you avoid years of unnecessary struggle, and time with family and friends boosts our morale. As a solopreneur, it’s easy to slide into working like a hermit, but you must resist the urge to disconnect from the world. Each day, choose one friend, family member or mentor (clients don’t count), and pick up the phone. This will eliminate the malaise that sets in when you dig yourself into your entrepreneurial foxhole.

When you practice these eight tactics consistently, you’ll still feel periodic bouts of panic—as an entrepreneur, this never goes away completely—but you’ll know that no matter what challenges arise, you have a playbook for dealing with them. 

This article originally appeared in the September/October 2021 issue of SUCCESS magazine.
Main photo by Photo by Nadia Snopek /

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