The 9 Hardest Things About Being an Entrepreneur That You Never Expected

Entrepreneurship is a massive undertaking which is often taken lightly by graduates and soon-to-be entrepreneurs.

This has been the key topic of my own book, 126 Steps to Becoming a Successful Entrepreneur: The Entrepreneurship Fad and the Dark Side of Going Solo, and I’m thrilled to have 9 other entrepreneurs chiming in and sharing their biggest pain points as founders.

If you have recently started your business or plan to launch one soon, make sure you follow these leaders and learn the ins and outs of running a successful company.

Expert Question: What was the hardest thing about being an entrepreneur that you never expected?

  1. Work-Life Balance

The 9 Hardest Things About Being an Entrepreneur That You Never Expected

I think it’s the work life balance. As an entrepreneur, we are driven to achieve and are willing to spend any amount of time getting there. But money nor success can’t buy back the time we don’t spend with our loved ones. That time could be worth more then we know.

Kirill Bensonoff, Parallel Entrepreneur, CEO OpenLTV

2. An Uncertain World
The 9 Hardest Things About Being an Entrepreneur That You Never Expected

Learning to live in the world of uncertainty.

Brian Silverthorn, Success Systems, Small Bizness Uprising on YouTube

3. Getting Things Done on Time
The 9 Hardest Things About Being an Entrepreneur That You Never Expected

As a highly motivated person, I didn’t expect for the smallest thing to take, sometimes, days to fix. I learned that “divided waters lose force.” It’s crucial to roll out your business methodically and expeditiously. Even the slightest acceleration can cause a delay. Don’t let your enthusiasm cause you to “overly multitask” and create unnecessary setbacks.

James Miller, Executive Producer and Host of the Nationally Broadcasted and Syndicated Radio Show, James Miller, Lifeology

4. Managing Professional Relationships
The 9 Hardest Things About Being an Entrepreneur That You Never Expected

The hardest thing about being an entrepreneur that I never expected, it’s that your colleagues are a family you choose. You will literally spend more time with them than your real family, they will reappear throughout your career, and they can be difficult to let go of.

Steve O’Keefe, Content Director, Orobora, Inc.

5. Building a Team
The 9 Hardest Things About Being an Entrepreneur That You Never Expected

Hiring, retaining and firing the people. It’s all about your team.

Barry Moltz, Small Business Expert

6. Handling Time Between Personal and Professional Stuff
The 9 Hardest Things About Being an Entrepreneur That You Never Expected

The hardest thing is managing work-life balance. It’s often said that becoming your own boss means having flexibility in your work schedule, but I haven’t found that to be entirely true. Being an entrepreneur is what I love, but there have been times when balancing work and family has seemed impossible. How do you explain to a customer that you’re late because you had to take your child to the doctor? How do you tell your child you can’t attend a school event because you have a business meeting that can’t be rescheduled? Being entrepreneurial has enabled me to find solutions for the balancing act, but it hasn’t been easy.

Barbara Weltman, founder of Big Ideas for Small Business, Inc. and author of J.K. Lasser’s Small Business Taxes

7. Impact of Self-Doubt
The 9 Hardest Things About Being an Entrepreneur That You Never Expected

The hardest thing about being an entrepreneur that I never expected is how much self-doubt can hinder your ability to thrive. Because you’re often alone and your goals are too far off in the distance, it’s easy to second-guess yourself, which leads to lack of action and/or taking incorrect actions, which makes the goals even farther off and this infinite loop of destruction and mayhem ensues. So find a good coach/mentor/advisor. Join a mastermind. Associate with professionals that are getting things done and continue moving forward. Now go sell something.

Wes Schaeffer, The Sales Whisperer®

8. Saying No and Staying Focused
The 9 Hardest Things About Being an Entrepreneur That You Never Expected

The hardest thing that I didn’t expect about was learning when to say no and staying focused. When you start a business, people present you with all kinds of ideas and opportunities—many of which are off target and take precious time and energy away from what you really need to focus on to to get your business off the ground.

Laurie McCabe, Cofounder & Partner, SMB Group

9. Changing Habits and Perspectives
The 9 Hardest Things About Being an Entrepreneur That You Never Expected

I think one of the hardest things was eliminating old habits that carried over from being an employee. For example, as an entrepreneur, I view time differently now than I did when I was an employee in the corporate world. How time is used is much more important than how much time is spent on something. Even as a leader, it was important for me to identify the leadership habits that worked in the corporate world but are ineffective in the startup environment. It has been a blast and a learning experience but it was definitely unexpected.

Ralph Jean-Paul, Managing Editor, StartUp Mindset

My Take

Entrepreneurship is about depth of expertise and breadth of understanding business dynamics. It’s not uncommon to stumble upon stalled startups founded by a veteran expert in a given niche or recent MBA students with limited industry experience.

Possessing both is a key trait you need to possess in order to progress. Work in a company or two for at least 5 years. Figure out how recruitment works, what does billing entail, what legal challenges threaten a business. Understand chain of command and what makes a successful manager, successful. In the meantime, develop your own skill set. You’ll definitely need both to step up your game as a founder.

This article was originally published on the author’s blog and reprinted with permission.

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Author: Mario Peshev

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