“Be your own boss.” It’s everywhere — Instagram Reels, TikToks, TED Talks, motivational books, maybe even Instagram captions. Imagine clocking in every morning … just to build someone else’s empire. Why let another person set your limits? After all, who knows you better than you?

You’ve been told to follow directions your whole life — first your parents, then your professors and now … your boss at work. Be the boss, or spend a lifetime working for someone who did.

Sounds promising, right?

But really — why does everyone want to be their own boss?
To avoid annoying managers?
To do less because now you decide?
To finally call the shots and have the power?

Take it from Whitney Goulish, who worked for over a decade in corporate leadership before launching her own business  — she says it’s not that simple.

“Stability is probably the hardest mindset shift when you’re working for someone,” said Goulish. “It’s there, right? Stability is there. Every day. You show up, you’re there, your paycheck comes.”

When you’re the founder, it’s a different story. “When you are a founder, you are grinding and hustling for everything. Every client, every position, every dollar, every everything.” Nothing is guaranteed. As the business fluctuates, so does your income. It’s not just a set paycheck anymore.

Goulish explained that it’s easy to lose motivation when you’re your own boss and make your own hours, but you have to remember that then you would be sacrificing the success of your business. It’s that realization that now you’re responsible for anything and everything that happens in you’re business.

This entrepreneurship tends to come with having to wear every hat. “You’re doing everything yourself. When you own a business, you are your own department. I don’t know of many companies that start and instantly have, you know, ten departments.” 

Having corporate experience before founding WG Business Enterprises was beneficial for Whitney in terms of habits and structure.

“When you work at a company, you’re working with people, you’re working with different departments.” 

Goulish continues, “Typically [a company has] either different services or products, Where if you go and start your own business, you don’t have any of that. You’re just going off of either your experience, your education, or whatever you have to go off of.”

When you go out on your own, you have to step back and reevaluate those habits. Ask yourself, “Was I just doing that because I learned that in my career working for others, or is it beneficial to running and operating a business?” Goulish said.

Because that’s the thing with habits — they are not always efficient, but they are automatic.

What Students Should Know

When it comes to early career mistakes, Whitney has experience as both an employee and a leader, and here’s what she’s noticed.

“The biggest thing for people that are younger is everybody wants a title,” she explained. Students tend to focus on landing a fancy title such as CEO, president or vice president. This is Whitney’s reminder that, “That’s not realistic. Very few times, seldom does that happen.”

But titles aren’t the only thing students chase. Many chase money too — and that, Goulish mentioned, can lead to another common pitfall: job hopping.

“Job hopping is a real thing,” she said. “Companies and businesses frown upon that.”

A business might associate you with being unreliable, inconsistent and potentially disloyal if your résumé shows a new job every year. This lack of commitment can tell a business that you’re not looking for a long-term commitment, making you seem like a poor investment.

“I think you need to have a very good reason why you’re leaving one job and looking for another opportunity,” Goulish explained. “And not just because someone’s going to pay you more money, because the grass isn’t always greener on the other side.”

 She advises to stick it out as long as you can and have a good reason for why you’re moving on.

If you do want to be your own boss, consistency and experience still matter. Rushing through these learning opportunities can leave you unprepared for entrepreneurial challenges. If you do want to be your own boss, consistency and experience still matter. Rushing through these learning experiences can leave you unprepared for entrepreneurial challenges.

“Get as much experience as you can, even if those opportunities are unpaid.” Goulish suggests that students take advantage of every learning opportunity and soak everything in. In the long run, the knowledge and skill sets you earn will make you much more valuable because they serve as the backbone for starting your business.

“The knowledge you’re going to gain and the real-world business experience you can take on is going to get you a lot farther down the career path, regardless of your industry, your position and whatever you’re trying to learn or study.”

 Everyone talks about networking — and for good reason. Goulish mentioned connections are helpful and almost necessary.

“Networking and connecting with others is going to take you a lot farther because, again, it’s about who you know and who knows you versus just being a number in an application pool with your résumé.”

 If there’s someone who knows you and can speak to your skills, don’t hesitate to reach out because every detail matters.

The connections you make now can potentially become your clients or partners that directly impact your business’s success. 

So yes, being your own boss unquestionably has its perks. Just know what you’re signing up for and prepare accordingly. Being a boss is not just about starting something, but sticking to it.

words_valeria palladino. 

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