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20 Entrepreneurs Explain The Hardest Thing About Running Business


Running a business is a no walk in the park. It’s coupled with challenging endeavors that can push us to the verge of giving up. Despite these challenges, it still remains a worthy venture in the long run. The results you get make us forget the hardships we’ve been through. We asked entrepreneurs and business owners about the hardest thing they’ve experienced in running a business.

#1- Learning to say no

Photo Credit: Louis Gudema

Owners have people coming to them with ideas and opportunities all day long, but focus is critical to success. For example, there are dozens of marketing tactics and thousands of companies selling marketing software; only by focusing on the few that can consistently produce results can you be successful. You can’t be distracted by bright, shiny objects, or even what competitors are doing.

Thanks to Louis Gudema, revenue + associates!

#2- Managing technology priorities

Photo Credit: Ryan Rosett

Today’s biggest challenge is effectively managing our technology priorities. Every stakeholder at the company believes their project is most important to the well-being of the company, and project timelines tend to overlap. Sometimes the big picture suggests that a certain priority will drive the most revenue, or that the ROI of another is higher. Managing expectations and keeping the teams rowing in the same direction is always top of mind as we navigate our growth from a post-start-up company and develop into a major player.

Thanks to Ryan Rosett, Credibly!

#3- Embracing change and leading people to scaling a business

Photo Credit: Phil Tee

Technology is a people business – our raw materials are talent. Finding great people and scaling the business go hand in hand. We are a rapid growth company so we have to be careful to change our processes accordingly at each stage of the company – what works for a Series A start-up is not what works best when you are at a Series C. So embracing that change and leading the people through the scaling of a business is naturally always the biggest challenge for a company such as ours.

Thanks to Phil Tee, Moogsoft!

#4- Getting the right support staff

Photo Credit:  Dr. Philip J. Miller

Getting the right people on the bus. You can have a great service business, but if you don’t have the right support staff in place, you will never realize your potential.

Thanks to Dr. Philip J. Miller, RhinoPlasty NY!

#5-  Remembering to think, not just to do

Photo Credit: Mark Chussil

Business culture venerates action. The hands-on executive, the boss who knows every facet of the business, the CEO who’s always engaged, the person who gets in early and stays late. If you’re a manager, executive, or CEO and you’re not doing something, what good are you? It seems indulgent, selfish, even lazy, to say I need time to think. But thinking is the one thing the CEO needs to do to make good decisions and take effective action. Here’s what you’re missing if you don’t take time to think. Contemplating the well-being of your employees and your family.  Considering the evolving needs of your customers. Pondering competitors’ next moves. Creating your next opportunities. And ensuring you’re living the life you want to live.

Thanks to Mark Chussil, Advanced Competitive Strategies!

#6- Remembering to take time to unplug and rest

Image Credit: Deborah Sweeney

One of the biggest challenges entrepreneurs face while running a business is remembering to take time to unplug and rest. Failing to do this can lead to burnout and it isn’t physically healthy for your body or mind. I find the best approach is to schedule in exercise each day, eat healthy, take your vitamins, meditate, and make it a point to unplug at least once a week so you can regroup and recharge.

Thanks to Deborah Sweeney, MyCorporation.com!

#7-Maintaining authenticity

Photo Credit: Andre Palko

In a world with countless “best practices” about how to do everything and anything related to small business, it’s easy to be tempted by “What’s everyone else doing that works?” But that doesn’t make me special. It just makes me like everyone else. What I’ve learned from others has helped me build a solid foundation. Yet I must not forget to include a little of my “uniqueness” in everything I do.

Thanks to Andre Palko, Small Business Rainmaker!

#8- Predicting timing

Photo Credit: Grace Lanuza

When your business gets to a certain point where you have to decide if you’re going to make some big moves, timing plays an important role in how the strategy will be implemented. There are many factors that should be taken into consideration: People for one, do you have the right people in the right roles at the right time? Do they have the suitable skill set in order to be set up for success? Another thing to consider would be readiness. Is your brand ready to make this move (Pro Tip: you will never be 100% ready so aim for 80% readiness)? Is your existing clientele ready for this big move or iteration of your business? And lastly, it would be opportunity. Does the opportunity exist? And if it doesn’t, what are you willing to do in order to create it? All in all, there will always be challenges to running a business so anticipate them and ensure you have a solutions-focused strategy to move forward.

Thanks to Grace Lanuza, Grace Lanuza Brand Strategy + Consulting Group!

#9- Time away from family

The hardest thing for me the last 14 years in being a business owner is the amount of time it takes me away from my family. The time commitment in running a business, and running it well is enormous. Spouses don’t often  understand, and children definitely don’t understand why we are so busy all the time. I work 12-14 hour days sometimes and it’s not an easy concept for my family to understand. I’m not one of those workaholic types but there is just so much to do that it is very difficult to fit it into an eight hour day. I own a micro-business, I have to do everything~ I design, create, photograph, and ship my products. I also have to promote, market and advertise them. I’m doing 5 different jobs in one. Time management skills are a must when owning your own business. There’s no time for lunches out, there’s no time for standing around the water cooler chatting about the past weekend’s events, it’s ALL work. My name goes out on every single product I send out, I want it to be a perfect transaction for each customer, I hold myself and my reputation to a very high-quality standard and I won’t except a half done job on anything. If I want to survive and stand out in an already incredibly saturated market, I must not accept anything less than the very best. Call me a perfectionist, but I have happy customers.

Thanks to GooseNiziolek, GoosieGirlBoutique.com!

#10- Various challenges

Photo Credit: Michael Risich

This changes with the time and success of your business. In the beginning it is the idea and creating it. But now my company has seen success at double-digit growth rates for the past few years. And now we are faced with many challenges, one that I am sure is common in many industries is a talent shortage. The ability for us to identify future team members that can be impactful is something that we strive to complete every day. Our team in the last five years has gone from five to nearly fifty, however we have amazing retention. We attribute that success to our culture and our focus to hire for the who first and then the assignment of what job. We have been very successful at solving this challenge, however the one thing that has remained as a constant is that we need to remain patient in this process.

Thanks to Michael Risich, BOLT ON TECHNOLOGY!

#11- Hiring and firing

Photo Credit: Richard Hayman

Employees are the lifeblood of every company. Think not? Without a great staff nothing works well. Having the right people, with the right attitudes and a willingness to be trained, is the primary job of every CEO. Do that well and the rest is easier. Making a motivated qualified employee work alongside of a slacker is the worse sin a CEO can commit. Treat and pay your staff very well and they will take you to heights you never dreamed of.

Thanks to Richard Hayman, Hayman Consulting Group!

#12- Embracing Skepticism

The most difficult part of starting my own business, my own personal brand, has been handling the skepticism I receive from others. At 23-years old, with a degree from Northwestern and a Masters from Kellogg School of Management, I’m supposed to be following a certain path in finance or consulting or marketing. I’m supposed to have stability, a salary, and opportunity for career advancement. But I have chosen to diverge from this path and go out on my own at an early age. I understand that this is the prime time to pursue something that lights a fire under me, to add value to others, and to craft a story that reflects adventure and spontaneity, rather than stability and monotony. This is why I write. This is why I am the author of Getting COMFY: Your Morning Guide to Daily Happiness. This is why I am building a movement that allows people to Get COMFY waking up in the morning, Get COMFY in their own skin, and Get COMFY with the rest of their lives.

Thanks to Jordan Gross, Getting COMFY!

#13- Keeping leads in the pipeline

Photo Credit: Brandi Holder

For me, the hardest thing about running a business is keeping leads in the pipeline. I believe the foundation of a successful business rests upon your ability to earn revenue during trying times. When the projects and the money are flowing, it can be tempting to stop sourcing for leads. To combat this bad habit, I schedule time each week to make contact with past clients and potential clients. During those meetings with myself I also take time to focus on defining what I do, and conversely what I do not do. The effort to pinpoint your services helps you refine your marketing efforts to address the pain points of your future clients. It can be quite time-consuming! However, defining your offerings and keeping up with customer leads go hand in hand with building a platform for success.

Thanks to Brandi Holder, Little Red Wagon Press!

#14- Managing expectations

Photo Credit: Jerry Haffey

For me, the hardest thing about running a business is managing expectations. In our industry, lives are on the line so it’s easy to get caught up and overwhelmed. I try to remind myself that the reason I started my business was to provide the best addiction care possible. Anything else is just a bonus.

Thanks to Jerry Haffey, Ambrosia Treatment Center!

#15- Realization that you’ll never be your own boss

Photo Credit: Kevin LaManna

The hardest thing about running your own business is the realization that you’ll never be your own boss. Every client is your boss. Not just the hiring person – but literally every single person on the client team. It’s not a bad thing, it’s just the truth. If you’re dealing with a project that has 30 people from the client side – then you have 30 bosses. Combine that across a couple hundred projects – and it can be slightly intimidating. Every client, every point of interaction from the people that you’re building things for – they’re your boss. Being your own boss is fictitious.

Thanks to Kevin LaManna, Monday Loves You!

#16- Being a little fish in a big pond

Photo Credit: Megan Saulsbury

The hardest thing about running a business is the fact that I am a little fish in a big pond. I offer the same services as larger agencies; however, I pride myself in that I provide my clients with the personal attention they may not receive at larger organizations. I knew this would be an ongoing challenge, so I’ve relied on my passion for my industry to overcome this obstacle. Utilizing my passion in all that I do has proved to be a wonderful and successful way to show clients size does not matter.

Thanks to Megan Saulsbury, Canyon PR!

#17- Wearing all the hats at the beginning

Photo Credit: Shannon Howard

The hardest thing about running a business is that, in the beginning, you’re wearing all the hats. Most of us come from some kind of career path where we probably specialized in something, and that’s our zone of genius. But when you’re starting your own business, you’re not just the content creator, the face, the sales guy, the ______. You’re all those things, plus the bookkeeper and the admin. With all that on your plate, it can be easy to get caught up in the minutia, get bogged down trying to learn something you don’t really need to know (graphic design, web design, and technology are all usually best outsourced, unless that your area of expertise), and not focus on the most important things (signing new clients/closing customers). So, in the beginning, it’s figuring out what NEEDS to be done, and what COULD be done, but could also be put off for another day to focus on the things that actually matter.

Thanks to Shannon Howard, You Need a Shannon!

#18- Responsibility of others

Photo Credit: Peter Chodelka

I run 2 companies specializing on Internet projects (affiliate marketing, e-commerce, videos). Response: For me, the hardest thing is the responsibility of other people. Three years ago, one of our projects got shut down by the government and 3/4 of revenues stopped in a second. It was hard to realize that 3 full-time and over 10 part-time employees wait for their wages and you have no money to pay them. I have not slept well for few nights, but as an entrepreneur, I have found a solution to overcome this.

Thanks to Peter Chodelka, Akontax!

#19- Early preparation

Photo Credit: Andrea Romito

Take whatever amount of resources you think you need to start a business: time, money, etc. and double it. Triple it. Because that’s the reality. Even with a well-thought-out business plan, always expect the unexpected. When I started designing the first collection for Nantucket Kids, I thought, I need to set aside the time and funds for the summer collection and then for the fall collection. Not true. That’s not how the fashion industry works. You need to prepare at least a year ahead because retailers are placing their wholesale orders up to a year in advance for their  inventory for the following year. This was something I hadn’t given consideration to because when I first launched the business, I hadn’t planned on taking wholesale orders. Now that Nantucket Kids is available in stores, the amount of planning, time and funds needed is trifold.

Thanks to Andrea Romito, Nantucket Kids!

#20- Living a balanced life

Photo Credit: Dave Bonnemort

Many times people become business owners to enjoy ‘the good life’ and have more ‘freedom’. It can be very difficult to balance being a parent, spouse and a business owner. Especially at the beginning when starting a business, owners typically find out very quickly that there is no one else to manage all of the different jobs. When the business is small, the owner wears many of the hats, so when a client is upset or something breaks down the owner is the one that has to stay late, come early or spend their weekend working on solving the problem. Ultimately, as the owner of the business the buck stops with you. The ‘good life’ ends up taking a back seat to get the job done, so money comes in, clients are happy, and the business stays open. As the business grows and more people can be hired to handle different jobs, typically this is when life can free up depending on the type of business and the goals of the owner. Work-life balance can be very challenging and is not to be underestimated, which is why I chose this as one of the hardest things about running a business.

Thanks to Dave Bonnemort, Anago Cleaning Services!

What’s the hardest thing about running your business? Tell us in the comments below. Don’t forget to join our #IamCEO Community

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