9
Be Your Own Boss
When I started my own business in my 40s, I admit it was scary, and it took a few years to get my income back to where it had been previously. But guess what? The psychic and emotional rewards of being my own boss and controlling my schedule are impossible even today to put a dollar figure on. They are priceless.
Being in charge of whom I work for and when and where is a dream. It’s empowering and liberating. I can still remember my last in-house job and that horrible feeling of being trapped, resentful of not being allowed to write stories that were my ideas because they weren’t in my “beat.” I had to drag myself to the office to even get there by 10 a.m.
It was a cacophony in the enormous newsroom with no buffering walls and reporters jammed together. I would watch the clock to see how soon I could escape. The anxiety was palpable. And then one day I quit and took off to New Mexico to write a book about Navajo weavers.
Stepping into your own business isn’t for everyone. I get that. But for workers over 50 in today’s workplace it’s increasingly common and will continue to be so. The digital explosion into every aspect of our working lives has enabled that. You can work virtually and run your show from home or wherever you may be.
Your work might be as a freelancer, contractor, or consultant. It might involve a full-blown bricks-and-mortar storefront or a manufacturer. Whatever its scope, it’s all yours. You own it. And the days of stressing over promotions and low pay, or grappling with job application rejections are behind you.
Before you get too far down the dreamy path of following a passion, there’s some work ahead. First, ask those central questions about the business you want to start: Why me? Why now? Why this product or service?
Your answers matter. This is your ultimate inner why. It’s important to be able to easily determine what distinguishes whatever it is you want to start.
MIDLIFE ENTREPRENEURS
The entrepreneurial movement started by Gen Xers and baby boomers has been gaining steam for several years now, but today it is driven by the massive economic shifts caused by the pandemic. If you experienced burnout and high level of stress, the prospect of being your own boss is positively liberating. Work-life balance has become a front and center priority. When you’re your own boss, you can have that.
The significance of entrepreneurship, or self-employment as a form of work, rises significantly with age, according to a report by Cal J. Halvorsen and Jacquelyn B. James of the Center on Aging & Work at Boston College.1
“While about one in six workers in their 50s are self-employed, nearly one in three are self-employed in their late 60s and more than one in two workers over the age of 80 are self-employed,” Halvorsen and James wrote.
For many workers over 50, “starting a new business by repackaging the skills and experience honed for decades into a new career is exciting,” said Nancy Ancowitz, a New York City–based career coach.
“It hits you, especially during the coronavirus crisis, that time no longer feels unlimited,” Ancowitz said. “You’re aware of your own clock ticking. Since you don’t have a seemingly endless vista of work ahead of you, you may be motivated to finally retool and learn a new trade, or just try something different.”
A buyout sum from an employer can be the seed money to fuel a venture you’ve been contemplating.
“For many of my clients, it’s that kick start rather than having to hunt for a job, with all of the loneliness and fear of rejection that comes with it, especially when they haven’t looked for a job in ages,” Ancowitz said.
The diversity of businesses started by people in midlife is strikingly varied—from selling nuts, bicycles, or jewelry to building websites or operating a food truck. I’ve been tracking boomer and Gen X entrepreneurs for more than a decade now, and I always smile when they tell me they just wish they had done it sooner.
“You can either see a world full of possibilities or a world full of obstacles,” Simon Sinek, author of The Infinite Game, has said. “Entrepreneurs are the ones who focus on the thing they want to create or build, rather than focusing on all things standing in their way.”
Studies show that entrepreneurs at midlife tend to have the highest success rates of any age group. A 50-year-old founder is 1.8 times more likely to achieve upper-tail growth than a 30-year-old founder, according to MIT economist Pierre Azoulay.2
Older entrepreneurs like you have a quiver of arrows to work with including management, marketing, and finance experience, and deep industry knowledge. Also—and this is significant—you may have more financial resources to tap and larger social and professional networks to reach out to for help. And if you’re starting a business in a field where you have work experience, all the better.
Intergenerational Businesses
You might even launch your business alongside someone younger, like your daughter, as Edith Cooper did.
“Many seniors are building legacy businesses alongside a younger member of their family,” Elizabeth Isele, founder of the Global Institute for Experienced Entrepreneurship, told me. “It’s a winning formula for both generations.”
Isele added: “When you’re over 50, you often want to create a business that has social impact on your community, if not the world. And frequently the younger workers carry the same sense of idealism on their sleeves.”
Cooper, who spent 20 years at Goldman Sachs, partnered with her daughter, Jordan Taylor, who was nearing 30, to cofound Medley, a career development platform based in New York City. They launched it during the pandemic.
To me, these intergenerational couplings exemplify a great strategy for future success. And you can expect to see more of these in the years ahead.
“Businesses that are staffed by multiple generations benefit from the different experiences and points of view that can make your business more responsive and more adaptable,” John Tarnoff, executive, career transition coach, and author of Boomer Reinvention: How to Create Your Dream Career Over 50 told me.
The 50+ entrepreneur often brings valuable years of experience, and the younger one counterpunches with the latest in technology skills and social media acumen.
A key benefit to founding a business with a family member who is decades younger is “the trust, commitment, and honesty that family brings,” Kimberly A. Eddleston told me in an interview. She is professor of entrepreneurship and innovation at Northeastern University in Boston and professor of entrepreneurship and a senior editor on the EIX Editorial Board of the Schulze School of Entrepreneurship at the University of St. Thomas in Minneapolis. “Family members are often more honest and open with one another, which can help in identifying and solving problems.” And when mistakes happen, Eddleston added, “They are quicker to forgive and move on.”
It was Taylor’s idea for a service to make executive-level coaching available to people at all ages and at all stages of their careers. Over two years, she and her mom honed the concept through discussions, exploration, and testing. Between its July 2020 launch and the fall of 2021, the women raised more than $5 million in capital. My guess is Cooper’s extensive network helped with that.
Cooper said the benefit of running an intergenerational business is that “it leads to an incredible amount of creation, innovation, and learning from both perspectives.” In hindsight, she told me, “When I was in a senior seat in my previous work, I always realized that ‘Boy, did I have a lot to learn from the younger generations coming into the workplace every year.’ The challenge is that you are coming at this from different perspectives. You have to be really intentional about not starting out a thought with ‘Yeah, but if you knew what I knew.’ That takes work.”
The duo’s advice for other intergenerational pairings: Focus on each of your separate gifts. “Big vision and an ability to draw connections—that’s what Mom brings,” Taylor said. Added Cooper: “I have worked in a variety of different environments with hugely different personalities. I see things that Jordan will eventually see, but it will take longer.” And Taylor said her biggest asset is her attention to detail and capability to hold a lot of things organizationally in her head.
Learn from each other. “Go into the relationship intent on learning,” Cooper advises. “To do that, you have to have an open mind and a fair amount of humility and the expectation that the other person has much knowledge that you don’t have, regardless of the generational difference.”
Be modest. Said Cooper: “There may be things I know given that I have had years more experience. But I also have years less experience in things that are native to Jordan, such as the leveraging of technology.”
KEYS TO SUCCESS
Isele, a guiding light in this playing field, and I have spent hours munching French toast and sipping steaming mugs of coffee at a tiny wood-paneled restaurant in Sperryville, Virginia. We talk about what it takes to be an entrepreneur at this stage in life, the challenges and rewards. She launched SeniorEntrepreneurshipWorks.com, the precursor to The Global Institute for Experienced Entrepreneurship, in 2012 at the age of 70. “Senior entrepreneurship is redefining the future of work and traditional retirement across all generations, cultures, and geographic boundaries,” she said.
The successful midlife entrepreneurs I have interviewed and worked with over the years share a common spine of smart moves they made to ensure their success:
• Those who succeed usually have an adaptable time span for their company to grow. They go slow. It can easily take a few years to get traction, and they plan accordingly both financially and personally.
• They did their research on the industry, the gaps they could fill. They added the essential skills, certificates, or degrees that were necessary before launching.
• They often apprenticed or volunteered beforehand with a comparable kind of job or business to see if it really is something that was as suited to them as they imagined.
• They reached out to their networks of social and professional friends and colleagues to ask for support and advice and sometimes help raising capital.
• They downsized and planned their financial lives so they could have enough money to get by until they were able to draw an income and to pay for the initial startup costs. Sometimes they were lucky to have a spouse’s or partner’s steady income or some independent investments, retirement savings, or pensions.
Some startups have grand goals and will require long hours and a weighty capital investment to succeed. Others can be simpler, such as a freelance consulting business or a craft shop on Etsy, a side gig making delectable macarons that you sell online while you work full-time as a veterinary technician. (Yes, that’s you, Melissa at Melissa’s Makery in Sperryville, Virginia.)
Halvorsen, assistant professor at the Boston College School of Social Work, an affiliate of the Center on Aging & Work at Boston College, told me. “Those who have higher levels of assets, spouses who have steady jobs, or families with a modicum of wealth are in a better place to start a business. If their ventures fail, they have something to fall back on.”
But the advantage is notable. Older entrepreneurs, Halvorsen said, “gain a whole lot of flexibility in their work, and that’s a major motivating driver for a lot of people. That does become more important the older you are. And they gain autonomy.”
USE FREE RESOURCES
Check out the free resources available to you. The US Small Business Administration (SBA) has regional Small Business Development Centers and Women’s Business Development Centers that offer state, local, and private grant information for those interested in starting for-profit or nonprofit businesses. SBA’s WBCs are a national network of 136 centers that also offer one-on-one counseling and mentoring to women entrepreneurs.
SCORE (Score.org), a nonprofit affiliated with the SBA, also provides mentoring and educational workshops nationwide. SCORE publishes a free e-guide called “Where’s the Money? 10 Most Popular Financing Sources and How to Qualify.”3
AARP’s Small Business website (aarp.org/work/small-business) is free resource. AARP and the SBA host events that offer counseling, training, and mentoring to see if you’re ready to start a business.
Explore the free entrepreneurship resources at EIX.org. Entrepreneur & Innovation Exchange (EIX) is a free peer-reviewed resource on entrepreneurship and innovation for entrepreneurs, innovators, and those who support them such as investors, advisors, and educators.
The AARP Foundation’s Work for Yourself @50+ (workforyourself.aarpfoundation.org/) offers free webinars and workshops as well as a downloadable toolkit with worksheets to help you set goals and more.
You can enroll in an online entrepreneurship course; many are free from universities such as Babson, Harvard, MIT, and the University of Maryland, and can be located on platforms such as Coursera and edX. The University of Pennsylvania’s Wharton School online has a Coursera roster of free courses on entrepreneurship. LinkedIn Learning has a decent selection, too.
For those retiring, or transitioning from military careers, Boots to Business (sbavets.force.com/s/b2b-course-information) is an entre-preneurial program from the SBA that’s part of the US Department of Defense Transition Assistance Program. It features an overview of entrepreneurship fundamentals and is open to transitioning service members (including the National Guard and Reserve) and their spouses.4
Pick up copies of my books, Never Too Old to Get Rich, What’s Next? or Great Jobs for Everyone 50+ (I couldn’t resist) as well as Encore.org’s vice president Marci Alboher’s The Encore Career Handbook; Chris Farrell’s Purpose and a Paycheck: Finding Meaning, Money, and Happiness in the Second Half of Life; John Tarnoff’s Boomer Reinvention: How to Create Your Dream Career Over 50; and Nancy Collamer’s Second-Act Careers: 50+ Ways to Profit from Your Passions During Semi-Retirement. All these books are inspirational and packed with resources.
DRAFT A BUSINESS PLAN
Create a solid business plan. Consulting with your financial advisor will give you a sense of what your personal assets are and what your options may be. Be certain that you have a good grip on the industry and those key questions: Why me? Why Now? Why this product or service? In essence, where is the need to fill a gap or solve a problem now?
In general, your business plan should include:
• An executive summary that states what your company will do, who the customers will be, why you are qualified to run it, how you’ll sell your goods and services, and your financial outlook.
• A full description of the business, its location, your team, and your staffing needs. You should also have a section on your competitors.
• A market appraisal that describes your likely customers, including age, gender, and location. The analysis also will explain your sales and marketing strategy.
• An estimate of startup costs—including raw materials, equipment, employee pay, marketing resources, insurance, rent, and fees for professional services (say, attorneys and accountants)—and what you predict your revenues will be.
Believe in yourself and take your time.
Funding Sources
When Jenny Yaeger, then 55, launched her Denver-based accounting and financial consulting firm for small and medium-sized businesses, ClariFI Business Solutions, in spring 2021, she used her personal savings. “Downsizing was what made it possible for me to go out on my own,” said Yaeger, former chief compliances and finance officer at Wakefield Asset Management.
Yaeger, who is divorced, purchased a condo with the proceeds from the sale of her home and had enough cash left over to cover startup expenses, such as purchasing equipment, hiring a coach to help with her business strategy, and joining a coworking space.
“Theoretically, my business can be run from my spare bedroom,” she said. “But I’ve really found that I needed to be out and about. And being in the coworking space is great support and networking. There’s a lot of women there building businesses; some have become clients and have referred me to others.”
To jump-start her business coaching new writers through the self-publishing process—Nowata Press & Consulting—Dana Ellington, then 54, of Kennesaw, Georgia, pulled $30,000 from a retirement account. She had launched her company as a side hustle while working full-time as an office manager.
“I was not ready to take that leap full-time until the pandemic brought so many things into perspective,” said Ellington. “The driving force was: I’m in my fifties, and if I don’t do it now, when am I going to do it?”
When you’re ready to launch, here’s a rundown of the funding avenues to consider:
Personal savings. This is the primary way midlife entrepreneurs fund their new businesses. The truth is, especially with virtual businesses, you don’t need to spend a fortune to get moving. “The costs of forming businesses have collapsed in many sectors, so the tap in to personal savings can be minimal, at best. You can spend a lot less than $10,000 to get off the ground,” said Jon Eckhardt, University of Wisconsin School of Business professor and editor in chief of the Entrepreneur and Innovation Exchange (EIX) of the Schulze School of Entrepreneurship at the University of St. Thomas in Minneapolis.
You’ll want to be vigilant to not exhaust any emergency funds you have socked away and be sure you don’t need the funds for living expenses such as a mortgage. I can’t emphasize this point enough: It’s common to not draw a salary for at least a few months while your business grows or if you opt to reinvest earnings into it.
Friends and relatives. They love you! They frequently lend capital at low or no interest. Be certain to put the terms in writing so that there’s no confusion about interest and repayment. Warning: Money can cause chaos on relationships should things not go smoothly.
Customer financing and consulting income. If your business will sell products, you can sell some of them ahead of production, according to Eckhardt. Also, he said, “You can earn early revenue by selling your time through consulting; use this revenue to finance the business and learn about your customer needs.”
Banks and credit unions. Scoring a bank loan is a hair-pulling experience for many borrowers. Lots of hoops to jump through from a paperwork perspective. And be aware they typically prefer to base a loan on your income as the barometer of your creditworthiness versus an asset-based one that takes into consideration your various investments, savings, and real estate holdings. A solid business plan and a top-ranked credit score are essential. You might approach a bank you already have a relationship with, or one familiar with your industry or known for small-business lending.
A bank that offers SBA-guaranteed loans with fixed rates is often a good route; check the Local Resources section of the agency’s website (sba.gov). A lender may want you to put up collateral, typically a real estate asset. You will need to show that you have also invested in your startup and will put a down payment on your loan. Business.usa.gov is the federal government’s site for entrepreneurs seeking short-term microloans and small-business loans. You’ll find information on all programs open in your state.
Economic development programs. These are available in cities, counties, and states. The SBA’s economic development department resources (sba.gov/about-sba/sba-locations/headquarters-offices/office-small-business-development-centers) can help you decide if this might be an avenue for you.
Angel investors and venture capital firms. This is a pipe dream when you’re getting launched, generally speaking. Depending on your future ambitions, these kinds of investors can be good to have on your radar. These investors invest in your business, but also want a part of it—equity or partial ownership. One caveat for women: This might not be the best route because women get a fraction of venture capital globally, and those who are Black, Hispanic, or Asian get considerably less.
Federal government. Another source of venture capital is the SBA’s Small Business Investment Company Program (sba.gov/funding-programs/investment-capital), which can provide an avenue for loans starting at $250,000.
You might also explore available grants at Grants.gov, which lists information on more than 1,000 federal grant programs. This is free money and not a loan, but it can be time-consuming to apply for and deal with the various hoops involved to wheeling your way through the red tape process in many instances.
Crowdfunding. Virtual fundraising campaigns on sites like Kickstarter, Indiegogo, and GoFundMe allow you to raise money for a new business in small increments—$10,000 would be a big haul. Find other businesses like yours that have crowdfunding campaigns and check out what levels they set for their goals. But if you’re trying to crowdfund money this way, you’ll need smart marketing chops.
It’s not an investment, so the money is all yours, and it’s a great way to build a customer base and mailing list, as well as get the word out in an organic grassroots way, particularly if you can share a product as a thank you for the contribution. Each of the big crowdfunding sites handles the funding process differently with various fees and percentages taken from credit card payments.
There are also a few crowdfunding platforms explicitly for female entrepreneurs, such as iFundWomen and Women You Should Fund.
Equity crowdfunding. Equity crowdfunding platforms are another avenue to raise capital. Republic (republic.com), for example, allows investors—not just well-heeled ones—to invest in private startups that have been meticulously vetted, with as little as $10 or as much as $100,000 per investment. Unlike the traditional crowdfunding platform, people who invest expect a return, but you generally have time to let your company grow. Although this is called crowdfunding because they put together a bunch of smallish investors to help you, it is an investment not a goodwill “shucks I want to support you” kind of contribution.
“Within crowdfunding, there’s a big difference between rewards-based crowdfunding and equity crowdfunding,” said Daniel Forbes, an associate professor at the Carlson School of Management University of Minnesota and a senior editor on the EIX Editorial Board of the Schulze School of Entrepreneurship at the University of St. Thomas in Minneapolis.
“Rewards-based crowdfunding involves soliciting donations from people in exchange for some goods or services that will be made available at a future date. This has been an effective approach for entrepreneurs in cultural industries, like moviemakers or musicians,” Forbes continued. “Equity crowdfunding, on the other hand, involves selling equity in your firm, and this is a more strictly regulated process.”
Home equity loans or line of credit. This may be an easy route because the funds are usually taken as a lump sum that you can pay off over time at a low interest rate. If you have equity in your home and a credit score well above 700, it may be worth investigating.
And now the two sources of money to use with care:
Credit cards. Most cards carry double-digit interest rates, which is a huge price to pay for launching a business. If you take this option, shop for plastic with the lowest rates and best terms.
Retirement savings. Retirement accounts should be used with extreme caution. Generally, you don’t want to dip into your 401(k) or IRA. Not only will you owe income taxes by taking money out, but you’ll also lose the tax-deferred compounding and, if you’re younger than 59½, you’ll owe IRS withdrawal penalties. Worst of all, you’ll potentially jeopardize your future financial security.
If you have a solo 401(k) already set up, you can borrow up to 50 percent of your vested account balance or $50,000, whichever is less. But here are some drawbacks. Interest on the loan is not tax-deductible. The funds you borrow are no longer invested, which may limit your opportunity for potential investment earnings. The loan must be repaid within five years of the date you receive the loan proceeds.
“Closing out the account didn’t really bother me,” Ellington explained to me. “I know a lot of people say you’ve got to plan for retirement, you’ve got to have the money. And, in the back of my mind, I guess I always see myself as working until I die. I am doing what I enjoy, willing to work harder at it, and I’m in it for the long haul. I’ve made it this far, and I trust myself to make it.”
GET GOING AND GET HELP
Get your business rolling, even if it’s part-time. Lenders consider your time actively working in the business when reviewing applications, and a track record is an advantage.
In today’s virtual workplace, for entrepreneurs, hiring a virtual assistant can be a godsend. Six months after Tamara Schumer, of Fairfax, Virginia, opened her home-based window-treatment business, she was swamped with clients.
“I was fortunate,” said Schumer, owner of Budget Blinds of Arlington & Alexandria. “But it was very stressful trying to handle customer service, scheduling, follow-up, orders, sales—all of that on my own.”
So, she hired a few virtual assistants to take on some of her responsibilities. “I needed somebody to answer my phone and my emails,” Schumer said. “I have an answering service, but they were very impersonal. I wanted to teach someone enough about the business so they could help me screen the calls and qualify the oppor-tunities.”
Schumer tapped FlexProfessionals (flexprofessionalsllc.com), a recruiting and staffing firm for the Boston and Washington, DC, areas, to help her find the right fit for her business. She started with a virtual office manager. “She answers the phone, schedules, and protects me from myself,” Schumer said. “If I answer the phone, I’m always saying yes to the customer and overscheduling myself. She handles customer service issues and reorders, so I can really focus on the revenue generation. It has been hugely helpful.”
Next, Schumer brought on a remote part-time bookkeeper. Although Schumer was formerly an administrative vice president at M&T Bank, in charge of the accounting basics, she detests those types of tasks. “This is my second career, and I wanted to have fun with my work. I’m spending money to have these women support me, but it’s enabling me to focus on the sales,” Schumer said.
“Our phone rings daily with calls from small businesses, many of whom are solopreneurs, stressing as their businesses take off,” said Gwenn Rosener, partner and cofounder of FlexProfessionals. “Some are running around with their hair on fire, trying to juggle everything from accounting to marketing to tax filing and not doing any of it well. Some are locked in paralysis; they have so much to do they can’t figure what to focus on, how to take a step forward.”
One thing entrepreneurs I interview frequently tell me is that, when they look back at what they would have done differently launching their businesses, they wish they’d delegated tasks sooner. But getting yourself to do this is hard. It’s easy to get into the superman or superwoman attitude that only you know what needs to be done and in a certain way. Meantime, bumpy revenue (particularly in the early days) can make it difficult to validate the expense.
If you do want to delegate some work, you can post a position on your industry association site or reach out to staffing agencies such as Boldy or FlexProfessionals, Work at Home Vintage Experts (WAHVE), FlexJobs.com, Upwork, and We Work Remotely. You can also post a virtual job opening on social media platforms, like a Facebook industry group, or do a search on LinkedIn ProFinder for the right freelancer for you.
WHEN CLIENTS ARE SLOW TO PAY
One of the most nerve-wracking things about being self-employed is dealing with clients who drag their feet on paying you, or run out on payment entirely. I was only stiffed once, thankfully. And it was one of the biggest media companies in the country. Needless to say, I have never accepted an assignment from that client again.
Most self-employed freelancers have problems getting paid at some point, according to research by the Freelancers Union (free lancersunion.org), the nonprofit group that promotes the interests of independent workers through advocacy, education, and services.
The best way to stop this from happening is to do a background check on the potential client before you agree to the assignment or project. Do you know anyone who has worked for them? What has their experience been with timely payment?
If you feel comfortable, you might ask privately in a members-only online LinkedIn or Facebook freelance group (or an independent workers group associated with your field) what others have experienced with that client. For me, on Facebook, that might be Binders Full of WRITING JOBS, a private group “for women and gender non-conforming writers of all backgrounds to share freelance, remote, part-time, and full-time PAID opportunities for fellow writers/editors.” It has more than 30,000 members.
If you’re doing your own billing and are not part of an online talent platform such as Patina (patinasolutions.com), Toptal (toptal.com), Upwork (upwork.com), or WAHVE (wahve.com), who will do the paperwork for you and collect the money, along with their cut, you need to be diligent about your bookkeeping and stay on top of what’s outstanding.
I generally give clients a 30-day grace period, but for speaking engagements, I require half up front when I sign the contract and half after the event. It is not out of the ordinary, though, to ask to be paid a portion up front or in several payments throughout the work progression. I do this for my book deals.
Get a contract. Skip the verbal handshake. Ask for an agreement in writing that you both sign that outlines the project, your pay, and when it is due.
You can create your own contract if the client doesn’t provide one. The Freelancers Union has a link on its website to walk you through the process of setting up a customized freelance contract. If it is a substantial project, you might hire a lawyer to vet it for you. I only use a lawyer to scrutinize book contracts.
Be certain up front that you have the contact information of the person in accounting that will deal with your contract and payment.
Set up a regular billing system. What works for you will depend on the kind of work you do. I generally invoice when a project has been completed and accepted, but longer-term projects may require a different approach with periodic payments that have been agreed upon in the contract, as suggested above.
Be aggressive about following up if a payment is late. Start with an email and then move to a phone call. But be tenacious. And save all documentation of your attempts to get your payment in full.
Hiring a lawyer to collect for you is a last resort. It can be costly and a hassle. A law, known as The Freelance Isn’t Free Law, in New York City, requires that for jobs paying $800 or more, freelancers must be paid either by a specified date or within 30 days of completion. The law mandates double damages and attorney fees be awarded if a case goes to court and the judge rules in the freelancer’s favor.
Wouldn’t it be great to see this law passed in other cities and states? If you only do one thing, report the deadbeat client to the Better Business Bureau.
HOW TO MARKET YOUR BUSINESS
Another common refrain I hear from entrepreneurs 50+ when asked about what they would have done differently before they launched is they wish they had more sales experience. Even if you plan to hire some-one to help you with sales and marketing, it still comes down to you.
Here are some sales tactics to help you market your business solo. Look for Help Wanted postings by potential clients on online websites like Upwork.com, Freelancer.com, VirtualVocations.com, TaskRabbit.com, and LinkedIn (linkedin.com/services). And advertise your own offerings there as well for someone who might be cruising for a professional who offers what your business does.
Set up company or professional pages on LinkedIn, Facebook, and Instagram. If you have a consumer product, do some stalking and see where competitors are posting their wares for customers to ogle. If you make a product, you can spotlight it on these pages. Sharing pictures of completed projects or products for satisfied customers. You might post a video of a work project from start to finish.
One of my favorite Irish designers is Maureen Lynch (maureenlynch.ie/). I discovered her work on one of my many trips to Ireland years ago, but now find myself ordering her pieces online from her website. I admit what has spurred me to do so are her 40-second videos in which she hammers away on a silver bangle or pendant and posts on Facebook and Instagram. They remind me of Ireland and the small horseshoe-shaped Sandycove Beach in Dublin Bay, where she lives and works and regularly swims. She posts pics of that, too!
Join a trade association affiliated with your line of work. Word of mouth is perhaps the most persuasive sales tool. Review association job boards and let other members know you’re available for jobs. You can even offer your services complimentary too and ask for references in return.
Self-employed workers often have websites where they list fees. You can also reach out to peers and see if they are willing to share ballpark figures of their typical price lists.
A website will help you pull in customers, and it’s a place where you can be “found” easily. It’s your own piece of virtual real estate to tell everything about you and your work and share all those lovefest notes from customers who are crazy about you and your business.
TAKE CARE OF DETAILS
Running your own business from home allows you to open and close the shop at will. You can walk your dog anytime you want. I do. It clears my mind and makes for a happy dog, too. But there are some general steps that you must do that aren’t as prosaic.
Secure the applicable permits—tax registrations, business and occupational licenses, and state and local government permits. If you belong to a homeowners association, make sure there aren’t any restrictions to running a business out of your house.
Update insurance policies. It’s generally a smart idea to add an insurance rider to your homeowners or renters policy to cover any expense should someone get injured on your property who is there for business purposes. Each state has its own rules about insurance. The Insurance Information Institute (iii.org), an industry trade group and information clearinghouse, is a place to begin your inquiry.
Set up quarterly estimated federal taxes on business income each quarter. Depending on where you are situated, it may be necessary to pay state and local income and business taxes, too. The IRS Self-Employed Individual Tax Center is a great resource to learn more, and, of course, make sure you have a trusted accountant on board.
You should, for example, be able to take a tax deduction for 100 percent of expenditures directly related to your home office, such as the purchase of a work computer. The other kind of tax-deductible home office outlays are “indirect” ones that are prorated, based on the square footage of your home and office. These are things like your mortgage or rent, insurance, and utility bills. To get the deduction, you must file Form 8829, Expenses for Business Use of Your Home. For full details, go to IRS Publication 587.
LEAD A BALANCED LIFE
Stick to a regular work schedule if at all possible. I personally work early mornings but avoid evening hours. That’s easier said than done, but it’s important to create a balanced work environment.
Vaccinated folks should look for occasions to connect in person with clients or colleagues for coffee or a meal. Attend industry seminars, go to conferences, and pop into local Rotary Club lunch meetings where other small-business people convene. Virtual ones, too, can give you a boost and help with networking and spread the word about your business. At the very least, call someone or have a Zoom chat in lieu of texting or sending an email. It’s energizing.
Running a home business can be lonely in the best of times. Creating a support group of other work-at-home entrepreneurs can be a solution. Russ Eanes, in his 60s, founded the editing and self-publishing business Walker Press and operates it from his home office in Harrisonburg, Virginia. He gets companionship and ideas by getting together with a small cadre of five other business owners. “My group meets virtually once per week,” said Eanes. “We learn from each other’s successes and failures. It helps that I don’t feel it’s just ‘me, myself’ out there.”
One element to the positive group interaction is that they are not competitors: “We are involved in different types of work, so there is a cross-fertilization of ideas,” Eanes said.
I find these groups a true salvation for solo entrepreneurs, specifically those facing trials when launching.
“I think it is a unique concept that can certainly serve as emotional support for struggling entrepreneurs,” said Donna M. De Carolis, dean of the Charles D. Close School of Entrepreneurship at Drexel University and a member of the editorial board of EIX, the Entrepreneurial and Innovation Exchange, funded by the Schulze Family Foundation. “The idea of a diverse brain trust group to flesh out ideas and challenges is a good one.”
I was taken by this concept, which has been a winning one for everyone from job seekers to women relaunching in the workplace in their 50s. So, I did some reporting for Next Avenue on what the secret sauce to making one of these jive for entrepreneurs working from home. This is some of the advice I gleaned.
Look for entrepreneurs at a similar stage of business growth as yours. “The key is to have some commonality among the members,” said Marc Miller, founder of CareerPivot.com. “In my group in the Career Pivot Community, everyone is early in their journey and is building largely a solopreneur business. They can help one another stay out of their heads, and, more importantly, be cheerleaders for one another.”
Outside input “keeps you grounded,” Miller noted. “When you get discouraged, you may need someone outside of your sphere to pick you up.”
And the participants could become allies. “I have a number of people in my group who have partnered up to either work on projects together, or used each other as a resource,” Miller said.
Stay small. “The goal is to bring together around 5 to 10 entrepreneurs on a regular basis—once a week or once a month,” said Fran Hauser, a New York City area-based startup investor and advisor as well as author of The Myth of the Nice Girl: Achieving a Career You Love Without Becoming a Person You Hate. “It’s easier than ever now to run a virtual meeting for an hour over Google Meet or Zoom, which allows you to invite entrepreneurs who don’t live in your town to join,” she said.
Create a varied group. When cherry-picking members seek out diversity in terms of ethnicity, gender, age, and personality types. This will bring differing viewpoints and stimulate conversation. To find members, tap into your LinkedIn connections, Facebook friends, your alma mater alumni group, and even your local Chamber of Commerce.
But Miller added a caveat: “It is valuable to have slightly different skill sets and experiences, but you also need chemistry between the members. I was asked to be part of a group a few years back. I went for about a month and found there was not a commitment from others to show up. And more importantly, I did not like several of the members personally. They were either too judgmental or critical of others. That was not the kind of environment I wanted to be around.”
Consistency is important. “I like to meet weekly because I need someone to hold me accountable,” Miller said. “Anything over a week in between meetings—it becomes difficult to do that.”
A steady check-in can be vital for your mental health as well as business counsel, particularly when your business is just getting off the ground. “In the initial stages of entrepreneurship, it’s imperative because that’s a period full of unknowns, self-doubt, and in many unfortunate cases, loneliness,” Nathalie Molina Niño, author of Leapfrog: The New Revolution for Women Entrepreneurs and cofounder and managing director at Known Holdings, told me. “It’s about connecting.”
Setting up an agenda can be useful. This keeps the meetings focused. In Hauser’s group, she said, “The members each share something they’re working on or struggling with, and the other members respond with thoughts.”
Two parting thoughts from a conversation I had with Alisa Cohn, executive coach and author of From Start-Up to Grown-Up. “Your company becomes a mirror of yourself, with all the good and all the bad. Self-examination before a launch helps you identify what leadership qualities you have, what qualities you need, and how you are going to make the most of your strengths, bridge the gaps in your skills, and strengthen some of your weaknesses,” she said.
“Second, in general, entrepreneurs are often known as control freaks, and only they can do it. The more you can delegate, the more successful you will be, even if everything is not always done perfectly perfect.”