How to Start a Business While Maintaining Your Life

18 questions to prepare you for the entrepreneurial journey

Entrepreneurship beckons increasing numbers of people today, offering greater control over lifestyle and livelihood. It offers financial freedom—the kind of wealth no cubicle dweller could hope to attain.

Many budding entrepreneurs already are ensconced in life, with its myriad responsibilities. They can’t simply make the leap into entrepreneurship without a safety net, so they carve time out of already demanding schedules to start and build their businesses. But for these entrepreneurs, the incomparable rewards of business ownership are worth the effort, discipline and time they invest. They say it is possible to start and build a business while maintaining a life—and they offer these tips, insights and questions to consider for maximizing your success.

Taking Stock

You first need to ask yourself, “Am I ready and prepared for and wanting the responsibility of owning a business?” suggests Carol Roth, business strategist and author of the New York Times best-selling book The Entrepreneur Equation: Evaluating the Realities, Risks, and Rewards of Having Your Own Business. She likens operating a business to having a child in that it requires constant nurturing, as well as time, money and effort. She suggests you take a good hard look at everything going on in your life—including your family and friends, hobbies and other pursuits—and ask yourself if you’re ready to make your business a top priority in your life.

1. Are you prepared to make a new business one of your life’s top priorities?

If your answer is yes and you’re ready to bring this virtual life form into being, you need to answer the following question next: “Who am I responsible for?” A small business has the potential to affect every facet of your life, and it’s only fair to consider how your loved ones—including your partner/spouse and kids—will be impacted by your new project. “Not only are they affected by your monetary decisions, these individuals are competing for your time and attention,” Roth says.

2. Who or what are you responsible for, and how will they be impacted by the new business?

Think about what happens if you lose your entire initial investment; What happens to your family in the worst-case scenario?

Dedicate some solid time to this thought process, and don’t make any hasty decisions; consult with your family, as well as trusted friends and advisors, for their input as well.

Reality Check

Be careful: Answering these questions with too much wishful thinking could be a worthless and potentially dangerous exercise. Excitement and passion for the business are very powerful factors—possibly the most critical factors in determining your success—but be realistic when considering your future. Nick May discovered the hard way that passion was no substitute for planning.

Working at a telecommunications distribution company in 1998, May started developing a contracting business on the side without giving much forethought to the project, he says. “I did not expect all the different things and responsibilities I had to manage as a business owner. I think when some of us start businesses for the first time, we think we are invincible, just like a teenager in high school. We think we know it all. We think our idea is the best.”

May managed to work through his initial startup issues. In addition to running that business, One Coat Paintings, a residential interior painting company, the Highlands Ranch, Colo., resident and father of two also hosts a radio show and carves time for volunteering.

But looking back on the experience, he says, “I should have gotten people around me to help identify my weaknesses and the things that I did not do well. I should have listened to others, talked to people who had done it before and planned accordingly.”

3. Are there people you trust who could provide an honest assessment of your weaknesses and strengths?

4. Will you listen and heed their advice?

Award-winning author, serial entrepreneur and investor Matthew Toren agrees that it’s important to be realistic about the future—without killing that initial optimism in the process.

“That excited feeling an entrepreneur gets when they have what they believe to be a great business idea can be a driving force to success,” he says. “The downside is that, if you let it, the excitement can also blind you to real obstacles that can hinder your success if not addressed properly.”

5. Is your excitement blinding you to real obstacles that could hinder your success?

Toren continues: “I personally believe that there are very few challenges that cannot be overcome. The question is whether someone is willing to do what it takes to make it happen. So you first have to know what it’s going to take. That means looking at your potential business from every angle, realistically. Seeing potential hurdles and planning for them is realistic. Saying that there are no hurdles is not optimism—it’s setting yourself up for failure.”

6. Do you have the finances, time and other resources needed to make your new business work?

Take a good, hard look at your available finances, time and other resources and assess whether you have what it takes to really make things work. This is also the time to determine what your goals and expectations are for the company and whether or not they’re truly feasible. Do your homework by consulting business books and periodicals, researching similar companies to yours and how they succeeded, and talking to other entrepreneurs, mentors, counselors or experts.

7. Have you assessed your goals and expectations for the new business—and are they realistic?

It also helps to look at your potential business objectively: If someone else were considering the same project, would you support them?

Take some time answering these questions and try writing down some of your thoughts on paper, because this early reflection—when done thoroughly, honestly and clearly—will serve as a steady foundation for your enterprise.

8. If a friend or relative were going to do what you want to do, would you give them the thumbs up? If not, what would be your reservations?

Juggling Act

As you go forward with your plan, you’ll soon discover that different areas of your life are begging for your time and energy simultaneously, and it may be difficult deciding where, when and how much to devote yourself.

Just ask Killian Rieder, a designer who had worked with some of the top names in the New York fashion industry before leaving to open her own jewelry shop in 2002. She and husband Jeff Julkowski expanded the brand, Chamilia, into a multimillion-dollar business by 2006—all while growing their family as well. Now as executive vice president and design director for the Minneapolis-based company, Rieder says that prioritizing is key.

“You need to plan and choose your top priorities and goals,” says the mother of two. “Stick to these priorities and don’t feel guilty when you say no to distractions. Recognize that life brings the unexpected. But when you have clearly defined goals, the focus is much clearer, and it is much easier to stay on track with your business.”

9. Are you willing to prioritize and set goals for various aspects of your life—and stick with those priorities?

“Prioritizing your life is critical because not doing so will inevitably lead to failure in whichever area you’ve neglected,” Toren says. “No part of your life—business, marriage, parenthood—can run on autopilot. If you focus on one thing and hope the rest will take care of itself, you won’t be happy with the results.”

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Making It Work—Set Boundaries

Name: Karen Bullard

Business: Paper Fancy, an online stationery and gift boutique based in her Manakin-Sabot, Va., home

Strategy: Because Bullard operates Paper Fancy out of her home studio, she says that “the business is always there and hard to get away from.” Being a perfectionist in nature, she’s constantly tempted to go online and tweak the site or answer that unopened email. So, in an effort to balance her work life and her family life (she has two kids)—as well as fit in time for volunteering—she has put strict boundaries in place. “Make sure you have definite ‘work time’ and ‘family time,’ ” she says. “Don’t let other things take up your time that you’ve carved out to complete specific tasks.”

To stay focused, she keeps her laptop in the home office and away from the home’s living area: “Our families need our undivided attention when we’re with them and not always distracted,” she says. Conversely, Bullard prevents her children from playing in her workspace. “I have stressed to my children that this is Mommy’s office and not a playroom or Staples store,” she says. “And they understand that.”

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10. Have you discussed and agreed upon these priorities with your spouse and other people who are significant in your life?

First, you have to set goals for the different parts of your life: “If you don’t know where it is that you want to go, you can’t figure out a path to get there,” Roth says. Especially when you’re starting out, it may be helpful to take the “baby step” approach of setting small, reachable goals for your business to help build momentum and avoid feeling overwhelmed.

11. Do you have the discipline to follow through with action steps you set to achieve your goals?

Then, deliberately devote the requisite time and resources to reach goals in each area. “Try following a set schedule that is divided into time slots for each area of your life,” Toren says. Tell your family and friends that you will be working in your home office every weekday from 9 a.m. to 3 p.m. and that you won’t be able to accommodate interruptions or personal phone calls or emails—and stick to the schedule religiously.

Sari Crevin, a former Microsoft manager and mother of two who founded the parenting products company BooginHead in 2007, allocates and maintains set hours with her family just as judiciously.

“Every day from 5 to 7:30 p.m. is strictly family time,” says the Bellevue, Wash., resident. “We eat together as a family and ban all electronics, including the phone, TV and computer. It is simply time to talk and play together as a family unit. Having that structure built in as a nonnegotiable helped create a balance that ordinarily and easily can get interrupted.”

12. Will you stick to your priorities and say no to distractions, or feel guilty and cave in?

Toren says, “The reality is that there will always be unexpected events in personal and business life that require attention now, regardless of what the schedule says. I’ve found that what’s most important is quality, not necessarily quantity. When you’re spending time with your family, be with your family 100 percent. Turn off the laptop and the smartphone, and focus on the here and now. An hour of that kind of family time will mean much more to them than three hours where you’re physically there but your mind is somewhere else.”

13. Do you have the resolve to adhere to boundaries separating business and personal life?

Devoting a set space to your work can also prevent distractions and help you get into “work mode” better. Just be sure to keep the boundaries delineated; you may want to keep friends and family members out of the office altogether so that the space’s function stays clear to you and everyone else.

Roth says that it takes constant vigilance, maintenance and self-scrutiny to ensure that your life—in all its varied parts—is on your desired trajectory. “You have to prioritize and re-prioritize often,” she says. “When times are tough at work, at home or both, remind yourself of the reasons you are doing what you are doing. Set a positive intention to carry you through. If the rewards don’t greatly outweigh the risks at any point, then stop and readjust.’ ”

Helping Hands

The road to a healthy business may be long and hard, but nobody says you have to go it alone. In fact, most successful businesspeople argue that having a proper support system in place is essential.

14. Do you have a support system?

The first fans to recruit are your family. “If your family isn’t supportive, you are going to be in an emotional state and susceptible to making bad decisions,” Roth says.

They feel the ramifications of your business decisions directly and indirectly on a daily basis, so strive to communicate with them. Explain to them your motives, your plans and how you expect they’ll be affected; then, in turn, listen to their questions and concerns.

“Listening to their feedback and respecting them to at least the same level you would an important client or investor will earn a lot more support than simply expecting them to adjust,” Toren says. “And, because having a happy family life will contribute in a big way to your ability to focus on your business with a positive frame of mind, family support is definitely critical.”

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Making It Work—Solicit Spousal Support

Name: Kara Buntin

Business: A Cake to Remember, a custom baking company run out of her Richmond, Va., home

Strategy: When the mother of two first started planning the business, her husband, Bob, “didn’t take it seriously,” she says. But, as she started earning profits and communicating with her husband about what was going on in order to engage him in the process, he understood her commitment and that she needed his help to succeed.

“I think that figures on paper speak louder than all the work that you put into something, and it’s just a matter of getting over that mental block to get someone to realize that you’re not playing around,” she says.

When Buntin is working, her husband takes care of the kids and treats the company as a top priority for them both. “He’s the one to ask me what I have scheduled for the weekend so that he can arrange his schedule around mine,” Buntin says. “He tells everyone about my business, and I know that he’s behind me.”

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15. Have you thoroughly communicated your plans and expectations, and how these will affect your family?

16. Will you listen to your family members and take their feedback as if they’re your most valued stakeholders?

Outside the home, building a professional support system can be equally beneficial. “We can’t do everything alone,” Roth says. “Plus, the more realistic information you have, the better.”

Toren agrees: “A lot of entrepreneurs are very independent, do-it-yourself people. This can pose a challenge if it means not asking for help or guidance.”

To illustrate his point, Toren refers to an anecdote from the world of sports: “When Michael Jordan was at the top of his game, few would dispute he was the greatest basketball player of his time—and maybe all time. When the team huddled to listen to the coach, was he standing off to the side, or was he in there listening, too? When they practiced and the coach was running the team through drills and providing feedback, do you think he paid attention? Absolutely. Everyone can benefit from guidance, especially from those who have already done what you want to do.”

One of the first resources to tap is your own network: Do you have friends, family, neighbors or colleagues who have relevant business experience—or do they know someone who does? “Ask your network about making introductions to people who have experience in similar industries, stage of company or who can answer specific questions you have,” Roth says, adding that local chambers of commerce, alumni associations and peer-coaching groups are options to consider as well.

17. Do you have friends, family, neighbors or colleagues with relevant business experience you can tap?

18. Do they have people they can introduce to you who have experience you can tap?

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Making It Work—Ask for Help

Name: Forrest Graves

Business: JumpinGoat Coffee Roasters, a gourmet coffee retailer in Helen, Ga.

Strategy: When he was laid off from Hewlett-Packard in 2008, this husband and father already had some ideas for his “Plan B,” as he and wife Debbie had long searched for the perfect cup of coffee and wanted to provide it via their own retailer.

But he needed guidance. “I found out pretty quick that many people wanted to give me free advice, but it was small-business owners who had the best advice.” Whenever he heard about a small-business success—through word-of-mouth, magazines or blogs—“I instantly wanted to know more about what and how they did things,” he says. “People who would take the time to teach or coach me were huge assets.”

Social media outlets such as Twitter, LinkedIn and Facebook have helped him meet like minded people within his community and beyond, and he also recommends trade shows, symposiums and seminars to listen to selected keynote speakers. “I was looking for battle scars,” Graves says. “I wanted to hear from the folks who did it.”

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Toren also points to social media as a powerful tool, which can help entrepreneurs connect with leaders in any field or location.

“If you’re polite but persistent, chances are you can get one of your industry’s icons to talk with you,” he says. “The biggest obstacle is often your own fear. Just remember that they are people, just like you, and most of them are more than willing to help out—because most of them got help from someone when they needed it.”