A Realistic Guide to Starting Out as an Entrepreneur

It’s Easier Than You Think to Get Started


Wesley Morton

3 years ago | 5 min read

A major perk of being your own boss, you choose where and when you work.

I’ve worked for other people for the last seven years. In that span of time, I’ve seen great and poor companies, had wonderful and horrible management, and generally learned a ton.

I fell into entrepreneurship three months ago, a weird combination of my own aptitudes, attitudes, and good fortune. I’ve earned about $5,000 in two months and built a growing pipeline of potential clients.

Here are a few things I’ve learned about entrepreneurship so far.

It’s Easier Than You Think to Get Started

The mental obstacles we hold in front of ourselves — the fears of the unknown, the what ifs, the self-doubts, the social expectations — are just mental. Simply starting is so often the hardest part.

The initial discomfort will be a familiar feeling for anyone who has tried something new. It’s the hero’s journey, the step into the unknown.

Truth is, the only thing you need to become an official business in the USA is an Employer Identification Number from the IRS, a business checking account, and something to sell.

The success stories of founders and business executives you so often read are written in hindsight. I guarantee you these entrepreneurial men and women were winging it just as much as you are now. You do not need to have everything figured out to get started.

I too doted for weeks on several decisions that ultimately have had no weight on my success or failure.

What do I call my business? Should I open an LCC, C-corp, or sole proprietorship? Do I need a new website and logo? You can figure out all these burning questions and unforeseen twists when they inevitably arise. Just start.

You Have to Do Everything

Remember Jane from accounting who handled invoices? How about Adam from IT who fixed your computer and email? Perhaps Stacy who helped you mail packages and handled the phones? You are all of these people now.

Be prepared to be IT, secretary, accounting, strategy, operations, and sales. Businesses scale when they acquire more business. When you are just starting out, you got no scale bub.

The biggest misconception I had when starting my creative strategy business was that I would be doing creative strategy. 75–80% of my time is spent on exploratory calls, sending emails, and networking.

If you don’t like sales, best to go work for someone else or find a cofounder that does. When starting a new business, you have to find all your own clients or convince someone to give you money to build something.

The upside is that it only takes one or two clients to sustain you. You don’t need anything for a service-based business but yourself, an expertise, and an internet connection.

Grab a client or two and start building a pipeline. Clients leaving you is inevitable, but there’s always a new one with a bigger checkbook around the corner.

A Lonely Experience with Highs and Lows

Clients are fickle things that tend to run out of budgets, go to competitors, take things inhouse, or fire you.

When a single email could change your fortune or ruin your week, expect emotional turbulence to be part of your daily life.

A signed contract with a deposited check is like hitting a homerun without a single fan in the stadium. Feels good but no one really gives a sh*t.

Your own drive is the only thing that’s going to sustain you through this endeavor. Cultivating an even head, exercising daily, and finding hobbies are all excellent ways to cope.

You’re going to want to talk about that homerun you sent sailing over the stands, but it’s hard to have watercooler conversations without employees or a watercooler.

Even when I chat with the creatives I employ, there’s a certain distance there. No one is going to tell the guy signing their checks about their recent custody battle, hot date, or latest booze-soaked weekend.

Founders and entrepreneurs tend to gravitate toward one another for the simple fact they have no one else to talk to.

Luckily the freelance and entrepreneurial community is less cutthroat and more supportive than I imagined. Your fellow entrepreneurs are great resources for wisdom, counsel, and referral business.

I’ve already set up informal partnerships with fellow agencies or freelancers that do media planning/buying, SEO, product development, design and events.

Referrals are an easy way to provide value to clients and receive a pipeline of new business for yourself.

Entrepreneurship is Freedom

The great paradox of entrepreneurship is that it’s a lot more work while offering you the flexibility to structure your own life. Each day is totally dependent on you.

The amount of time you put into your business, how you brand yourself, the type of clients you go after, the quality of your work, and the people you hire are all a factors that depend on you. If you don’t do it, nothing gets done.

Work from anywhere, pursue what you love, and pick your path.
Work from anywhere, pursue what you love, and pick your path.

I find myself always working. Taking calls on weekends, finishing a proposal at night, sending prospecting emails throughout the week. However, I choose to do it.

Don’t feel like working on Friday? Clear your calendar. Want to work remotely from a Caribbean island? Do it. A difficult client causing you headaches? Drop them. Each day is completely mine. I choose to pursue what I want.

My initial trepidations on taking the leap evaporated when I broke down the worst-case scenario — I fail miserably and go work for someone else. Any risk-taking endeavor comes with a negative possibility, but a negative result is not nearly as bad as we believe.

More often than not, the worst-case scenario is simply the status quo. You are no better or worse off for trying, and you’ll definitely learn some things along the way.

Entrepreneurship isn’t for everyone. It requires adaptability, sales, intrinsic motivation, and can be a lonely, emotional rollercoaster.

For others, the flexibility, freedom, and excitement that come with it are addictive motivators to build an ideal life. Examine your situation now. If the entrepreneurial life calls you… what have you got to lose?


Created by

Wesley Morton







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