5 Tough Questions to Answer Before You Strike Out on Your Own
Brendon Schrader, the founder of Indypendently.com and consulting agency Antenna. (Photo courtesy of Tom Ziemer)

5 Tough Questions to Answer Before You Strike Out on Your Own

Make sure you can answer these five questions confidently before starting a business of your own.

When I set out to launch Antenna 12 years ago, I was dangerously optimistic. Today we’re a thriving company with almost 100 employees, but I couldn’t have known that when I started. I believed I had a great idea and boundless energy. I worked hard, got lucky, and learned a lot along the way. Now as the founder and executive editor of Indypendently, an online magazine full of inspiration and advice for solo workers, I’m passionate about helping other brave independents start strong and make sure that they’re ready for the (incredibly rewarding) adventure of going solo.

If you’re serious about starting, spend some time making sure you can answer these five questions with confidence.

1. Know your why: What’s driving the change?

The leap into a solo career is not to be taken lightly and is not right for everyone. Whether you’re driven by an idea of what could be, or an opportunity you see clearly, do some reflecting about the larger forces behind the change you’re making, and make sure that striking out on your own is really the right move.

People’s work-related unhappiness tends to fall under three categories:

  • Career trajectory: Where are you in your career, and are you happy with that? Have you advanced on the path you expected?
  • Type of work: Are you challenged by your work? Do you feel fulfilled and motivated? Are you learning and growing?
  • How you work: Are expectations about when, where and how you work interfering with your personal responsibilities and priorities?

Once you know why you’re unhappy, you can make sure that what you’re creating isn’t just another version of what you’re trying to leave behind. Can you change jobs? Can you pivot your career? That being said, if you see the independent path is right for you, don’t waste any more time – get started. Now.

2. Identify your gap: Where does your passion meet the market need?

Having a great idea isn’t enough to succeed in business. Neither is “following your passion.” I recently spoke with a well-known entrepreneur who emphasized the importance of focusing on the frustration of your end-user. “If you can consistently ground yourself with the empathy for those suffering the problem, I feel like that’s the force that helps you get closer and closer to what we call product-market fit,” he said.

To get a read on the market, have conversations with your target buyers. Let’s say you want to sell design services to marketers at small companies. Go talk to a few of them. Ask them how, if, and why they might need what you’re offering. How are they filling the need now? What would make that process easier for them?

Once you’ve determined the market demand, consider different avenues to get that business. If you target big companies, they’re often hard to get into and get approvals, but that means once you’re in, you’re really in. If you go after smaller companies, they’re likely easier to get into, but budgets are more limited. Understanding how the market works for your specific industry or service area will influence how you’ll sell your services.

3. Talk to people who made the leap: Who can you learn from?

Think of networking as learning from others who have what you want. People who love their job want to talk about it. It’s why I happily give advice to marketers and independents who are stuck. I created a career I love, and I want to help others do the same. A career coach I know suggests thinking of networking as “research, not sales.” “Approach people with genuine curiosity and an interest in learning more about who they are and how they got where they are,” she says. Good advice.

Don’t give them your resume at the end of the conversation. Just thank them for their help and think about how you can apply the lessons. And, most importantly, stay in touch with them to keep the relationship going long term.

4. Know yourself: What are your strengths?

To succeed solo, you need a deep understanding of who you are and what’s important to you. What are you naturally good at? What do you love to do? What gives you energy? Also, just as important: What do you hate doing? What are your weakest areas?

When you understand your core personality, you can better predict how you’ll react to the new scenarios you’ll face as an independent worker. If you realize, for example, that you’re an introvert and don’t like aggressive networking, you can flag that as a weakness and figure out how you’re going to compensate (by outsourcing, taking a class, or hiring a coach, for instance).

5. Get help: Who do you need on your team?

Whether or not you ever plan on hiring employees for your new venture, there are a few key partners you need just to get started. When I started working solo, I relied on my attorney, accountant, and my insurance adviser.

My attorney helped me create my business entity, along with the basic contracts I’d need to work with clients. I needed a way to outline an engagement — the services I’d provide, how to protect myself and detail out the payment terms I’d expect from clients. Some clients will ask you to sign their contracts, but you need your own too.

My accountant helped me think through how I’d manage taxes and financials. There’s a huge benefit to working proactively with an accountant so that you set up your taxes correctly up front and don’t get hit with a big tax bill later in the year. An accountant can also help you think about how to classify business expenses such as networking coffees, meals with clients, mileage on your car as you drive to meetings, insurance, computer and your cell phone.

Insurance might not seem critical right out of the gate, but many clients and partners may require that you’re covered before you start working together. And you don’t want to figure this out at the last minute when a client requests proof of insurance. Ask your insurance partner for advice on what types of insurance you’ll need.

Setting up these crucial partnerships will ensure your ability to quickly engage with interested clients. And, more importantly, you will immediately give your clients a feeling of trust and confidence that you take this seriously.

You also need to make sure that you’re set up with the right support network. Do you have a mentor to help you grow? A cheerleader you can turn to for a little boost of confidence? A (friendly) challenger who will push you and make sure you’re staying true? These kinds of peers and colleagues are just as important to your solo success as your professional partnerships, so make sure you know who they are, and you check in regularly.

There are no guarantees when you decide to make the transition into a new venture, but it takes more than determination and hustle to succeed. Take the time to ask the tough questions if you’re serious about setting yourself up for success.

Brendon Schrader
Founder/CEO of Antenna
Founder/Publisher of Indypendently.com

Brendon Schrader is the Founder/CEO of Antenna, a Minneapolis based marketing consultancy. He is also the Founder/Publisher of Indypendently.com, a content and media platform for independent workers. Brendon’s insights on independent consulting, the gig economy, the changing nature of work have been highlighted in  Inc. magazine,  Forbes, Fast Company, and the Huffington Post. He holds an MBA from the Carlson School of Management, an MEd from the University of Minnesota’s College of Education and Human Development, and a degree in Business Administration from the University of Minnesota Duluth. Brendon has also studied leadership, strategy, and innovation at Northwestern University’s Kellogg School of Management.​