• Home

  • Business growth

  • Business tips

Business tips

6 min read

6 obstacles every early-stage business owner should expect

By Liz Melton · August 1, 2023
A hero image of a woman at a coffee shop on a computer

It's officially been one year since I registered my S-Corp. Since I've already popped the champagne and had a bit of a celebration, I thought I'd recap some of the biggest lessons I've learned on my business owner journey.

If you're about to open a small business, here's what you need to know.

The unexpected obstacles small business owners face

When you Google how to start a small business, you'll likely come across resources for estimating market share, picking a business name, managing variable income, and the like. Each topic plays a role in owning a business, but they're only part of the whole deal.

The other parts? Well, I wasn't quite prepared to manage those at first, but now I have some strategies to overcome them.

1. Fear of the unknown

Starting your own business is scary. Even if you know deep down that you're good at what you do, self-doubt always seems to creep in. What if you can't get it off the ground? What if no one likes your product? What if you can't get an SBA loan?

The what-ifs keep coming. And if you let them, they'll keep holding you back. 

My best tip is to start your business while you have a full-time job. I pursued my content strategy business on the side for over three years before I took off on my own.

It was tough, yes. But it allowed me to work out the kinks, nail my ideal client profile, and improve my writing. It also gave me space to learn new skills in my B2B SaaS operations job that would serve me well in running my business long-term. And, perhaps most importantly, keeping my job meant I could build up my savings so that I felt comfortable making the leap.

2. Self-promotion

As an introvert, I hate nothing more than talking about my accomplishments. But as a business owner, it's absolutely necessary. You have to be willing and able to tell everyone about your new business: friends, family, colleagues, past coworkers, and your LinkedIn network.

If it feels disingenuous to brag about your work, I recommend leveraging testimonials—that way, others can do the bragging for you.

A testimonial from Liz's website

If you run an agency or are a solopreneur, consider investing in courses to help you craft your social media posts. I recently purchased Justin Welsh's The Content Operating System and Impactful Social Writing by Erica Schneider and Kasey Jones.

If you still feel uncomfortable, hire someone to ghostwrite posts for you.

3. Legalese

It takes time to read all the fine print and determine how to structure your organization, let alone your LLC or S-Corp application. You also have to create sound contract templates and/or review the detailed contracts enterprise clients use before you can start your work.

Eventually, I gave up doing it myself. It was wasting too much time and putting my business at risk. Instead, I hired an accountant to review the pros and cons of opening an LLC vs. an S-Corp and used a firm they recommended to set my entity up for me. I got my S-corp approved within a week.

If you aren't sure who to hire, try scheduling an appointment with a local SBA officer. They can point you toward funding programs, counseling, partner organizations, lenders, and other community groups.

4. Capacity planning

In a 9-to-5 job, you're doing a set number of things every day, and your boss and team are there to hold you accountable.

When you're a business owner, all of that disappears. You're the one juggling a million things at once—inventory, accounting, billing, marketing, client management, the list goes on. Fitting everything in is like a giant puzzle you simply have to get good at if you're going to succeed.

The biggest gift you can give yourself is to get organized. Find a project management tool or process that works for you and stick to it. 

Liz's assignment tracker in Notion
This is my assignment tracker in Notion.

A few tips here:

  • Keep in mind that you probably only do your best work within a certain time frame of the day. Know when your productive hours are, and set that aside as work time only. As a former elite athlete, this was hard for me. When I was training, my day would start early in the morning, so I'm wired for action as soon as I wake up. Normally, I'd go for a run or do a hard workout first thing. But when I started my business, I realized I was giving away precious focus time, so I switched my workouts to the afternoon instead.

  • Practice estimating how long it'll take you to do something is critical as well—otherwise, it's impossible to manage your schedule. Time tracking apps can be a big help here.

  • Leave more time for the unexpected than you think. This is a lesson I learned the hard way. I had a tendency to accept new business without taking into account all the other things I had on my plate besides client projects, like edits, QuickBooks, marketing, and continuing education. Before I knew it, I had no room for these tasks, let alone emergencies. Building breathing room into your schedule is the only way to deliver your highest-quality work.

5. Late payments

After you finish a project, you don't want to wait months to get paid. Unfortunately, that happens often, particularly for professional service business owners. If you have some cash in an emergency fund, you might be ok for a while, but being out a significant chunk of money adds unnecessary stress to your life. And it's certainly more of a burden if you're on the hook for employee or contractor payroll.

Only some clients will agree to it, but I recommend adding payment terms of Net 15 to your contracts. It will (hopefully) speed up the payment process and enable you to enforce those deadlines. And set up auto-reminders for customers or clients that haven't paid you.

It can also pay (pun intended) to check your city and state laws. For example, the Freelance Isn't Free Act (§ 20-929) in NYC stipulates that the hiring party must pay no later than 30 days after completion of the freelancer's services under the contract. Gently remind your clients of these laws—it should help.

Finally, contemplate charging interest on late payments. This is a great piece that freelance writer, Wudan Yan, wrote about how she handled $5,000 in late fees.

6. Loneliness

There's one major thing I miss about my full-time jobs: my work friends. I miss laughing out loud, shouting out colleagues on a job well done, and commiserating during tough times.

Liz's home workspace
This is my workspace at home. I love it, but I need a change of scenery sometimes.

Building these kinds of relationships when you're a small business owner is hard. But the cool thing is, you're the boss—you can, and should, make time to nurture them. Here are some ways to do it:

  • Block off in-person and phone dates in your calendar. I hike every week with a friend that lives close by and have regular chats with my friends every month. I can't tell you how much I look forward to them.

  • Change up your workspace. I rotate between my local library and my favorite coffee shop, but you could also reserve a desk at a shared workspace. Even though I'm not actively talking to people besides the barista, it feels good to be around people.

  • Take a weekday off. My husband (who is also a small business owner) and I stop working every Friday around 10 a.m. and spend the rest of our "date day" doing whatever we want. Although we work in the same house, setting aside this quality time allows us to catch up, recap the week, and do something fun.

  • Sign up for a hobby-related class. Getting out of the house does wonders for your mental health. Plus, the people you'll meet are guaranteed to have something in common with you. I chose a beginner dance class.

You can do this

The hardest part of all? Taking the first step. But once you do, you have the power to create the type of business and lifestyle you always wanted. Need some more motivation? These resources might just give you that nudge you need:

  • Why starting a side hustle makes you a better full-time employee

  • 57 best businesses to start with $10K or less

  • How to start a business with no money: 22 low-cost business ideas

  • Business startup checklist: How to launch a startup step by step

Get productivity tips delivered straight to your inbox

We’ll email you 1-3 times per week—and never share your information.


Related articles

Improve your productivity automatically. Use Zapier to get your apps working together.

Sign up
A Zap with the trigger 'When I get a new lead from Facebook,' and the action 'Notify my team in Slack'