Life & Business

5 Questions to Ask Yourself When Starting A Business

by Lauren Chorpening Day


It’s an exciting time for creatives craving more autonomy in their work. Freelancers, small business owners and entrepreneurs of all types are becoming more common in the workplace and are taken more seriously by larger corporations, potential clients and consumers. It’s easier than ever to start making strides to self-employment. Today Liz Lidgett, art advisor and founder of Adore Your Walls, is sharing her experience of starting her own business and advice she gives when asked what it takes. –Lauren

Photography by Rick Lozier and Austin Day

Liz Lidgett: After nearly five years of owning my own business, I have found a new passion: helping people to quit their 9-5 jobs. Becoming an entrepreneur was one of the best decisions I have ever made. It allowed me to take control of my career and paycheck and gave me the flexibility to lead the life I want to live. It’s not about being irresponsible — quitting your job is not for everyone [and it’s a big risk] — but we get too convinced that we have to have this or that job, even when we hate it. I just enjoy reminding people that there are options. When someone realizes there’s a way out of the position they feel trapped in, the most glorious light comes on. Still, there a few questions I like to ask people before encouraging them to make that leap.

1. Are you happy?

The year before I began Adore Your Walls, I was unhappy. I was working for a great company, had a job that looked amazing on paper. I had (and still have) a wonderful, supportive husband, amazing friends and family, a roof over my head, etc. I had so much going for me but my job was bringing me down. I decided that life was too short to lead a life that makes me unhappy. So if you’re unhappy with how your life is going, it’s time for a change. If your job is affecting your happiness, it’s time for a change. But what change will make you happy? I started a list of all of the things that I loved doing at my job and in my day-to-day life. That initial list was the basis for my company.

2. Do you have a plan?

Once I decided to start my business as an art advisor, I tried to plan as much as possible without getting stuck in the minutiae. I first looked at all of my finances and found my “number.” That was the number I knew I had to make every month to survive — food, living, etc. It was a bare bones number with no extras added into my budget. No new running sneakers, no manicures, no dinners out. But I knew the sacrifices and pay cut were worth the risk to start this business. I then worked with the local Center for Economic Success to review my business plan. Having those extra sets of eyes was invaluable to me to start off on the right foot. My plan showed what I could get by without at first (an office space, advertising) and what I needed right away ($20 a month for Quickbooks online). I started with as little overhead as possible. I needed two retainer clients to quit my job and the day I got them; I gave my notice.

AYW for DS0134

3. Do you have a support system?

No one can make it alone. One of the biggest factors I look at for success is the type of support system a potential entrepreneur has around them. This will include people to give you a pep talk when you’re feeling lost, mentors who have been in your shoes before, and friends who can take you out for a margarita when that big client meeting goes really well (or really poorly.) You will have wins and you will have losses. You will hear “No” far more than “Yes.” It will be hard and it will be amazing. The people around you will help you keep your eye on the prize and your head on your shoulders.

4. Do you have your first clients?

Who will use this product or service? Can you identify a list of 100 people or companies that need your company? Talking about this before you quit your job can be a delicate process. I always worked after hours and made sure that I would not be harming my current position or company. Past that, I talked to a lot of people about my idea. I reached out to potential clients through LinkedIn and through personal connections. When people started reacting positively — and agreeing to business relationships — I jumped ship.


5. Are you ready?

My parents tell me frequently, “If you wait until you’re ready, you’ll never do it.” So I believe in the right combination of planning and faith. You don’t have to have every client you’ll ever want pinned down. You don’t have to know how you’ll use every minute of every day. Here’s what you do need: an even temperament. Don’t let the highs get you too high, or the lows too low. You need the ability to be told “no” and keep going anyway. You need a belief in yourself and a working knowledge of the field you’re entering.

People often ask me if I was scared to quit my job and start my own company. I tell people that it was scarier to stay than it was to leave. If you can answer all of the questions above with a “yes,” then get going. I’ll be here cheering you on.

Suggested For You


  • A terrific breakdown for entrepreneurs of the basics of starting a new venture. I wish I’d thought about these 5 questions before I started my subscription business 3 years ago. Trying to figure things out as you go is not the best way. Thanks!

  • “I tell people that it was scarier to stay than it was to leave.” -This hits home. I feel more scared thinking that this life ( a 9 to 5 job) is all there is. Sometimes, taking risks is what makes you feel more alive.