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One of the exciting things about starting your own company is that you can do it any way you like. There are best practices to lead a team and common ways to set up your business model, but ultimately you pick which path you want to blaze.

When Tracy Sun and Manish Chandra founded Poshmark, which makes an app that lets users sell clothes from their closet, they decided to do it their own way. Sun talks about how entrepreneurship is a personal adventure.

Image Courtesy Poshfest.

Image Courtesy Poshfest.

As a kid, I loved those “Choose Your Own Adventure” books. How boring is it to read a book where someone has already told you exactly what has happened to your hero? I couldn’t write my own book, so being able to choose A, B, or C was good for me. That sense of adventure to the nth degree is what starting a company is like,” Sun tells us “The kinds of problems you’re solving, or trying to solve, have not been solved before. … That to me is super fun and full of adventure.[1]


Asking the tough questions

What do I want to be when I grow up?
How do I want to spend my days?
How can I use my skills in a productive way?
What is my dream job?
And, most importantly, how can I make that dream a reality?

These were the questions I asked myself. I started answering these questions by looking at my priorities and responsibilities, and finding a way to fit work around those items, not the other way around, as is the more traditional model.


Finding Balance

Some of us assist with care for elderly parents and grandparents. Some of us want the freedom to travel. Some of us train for triathlons or other athletic endeavours, and need to devote time to that during regular work hours. (Not me, by the way. Just in case anyone’s asking.)

With two kids, and a husband who works out of town, it’s often a one-parent show here. What I wanted most in my work-life balance was the flexibility to manage my family without being stretched to the breaking point; something many working parents experience. I want to be able to take a day off if the kids are sick. I want to be available to pick them up after school and take them to gymnastics and dance classes, or just hang out at the beach. I want to have time to volunteer in their classrooms or on field trips.

Having my own business and working from home allows me the freedom to do all those things. As with any good adventure, there are possible snake- infested rivers to be paddled and dense jungle trails to cut. I spend a lot of late nights at the computer to keep my business from making that unfortunate plunge over the cliff edge. But this is the adventure I’ve chosen. There is incredible power in that.


Creating Your Ideal Life

I don’t believe that life happens to us. I believe that we make it happen. I’m an active participant, the main character, hopefully even the hero of my own story. There is no “I can’t possibly make this happen”, only “How can I make this happen?” If having your own business and working from home is what you want, you can make it happen. By determining your priorities, and deciding what you want out of life, you have taken the first steps towards making that dream a reality.

Photo Courtesy Business of Life.

Photo Courtesy Business of Life.

Being self-employed from my home office is the adventure I choose every day. Have you chosen yours? How can you make it happen? [2]


Another Story

Ed Packard was a lawyer for RCA records. But it wasn’t his true calling. Ed wanted to be a writer, and one fateful night back in 1969 he was telling his daughters Caroline and Andrea a bedtime story about a character named Pete marooned on a desert island.

I was tired from a long day at work, and I couldn’t think of what should happen next in the story. So I asked them. I got two different answers. I could sense that this was an unusual approach. They could not just identify with the main character. They could be the main character.

Ed penned his first book on the train from his home in Connecticut to his law office in New York. He got an agent at William Morris who told him his first book “The Adventures of You on Sugar Cane Island” would be a big hit. But after countless doors were slammed in his face by children’s book publishers who told him his work was more like a game than a book, Ed gave up.

He put his manuscript in his desk drawer and left it there to collect dust.

It was only after he met a young literary agent named Amy Berkower through an old college buddy that the books finally got a good, hard second look a decade later. And with the help of another upstart in the publishing business, Joelle Delbourgo at Bantam, “Choose Your Own Adventure” exploded into a phenomenon that rewrote the book on children’s literature. [3]


The unfinished business

Small businesses can be vehicles for achieving a multitude of social as well as economic goals. During this talk we tried to convince the audience that doing their own thing can be extremely rewarding and fun.

You’ve dedicated countless hours to building your business, but eventually, the time will come to move on to the next chapter in your life. Whether you’ve reached your goals, the business has outgrown your vision or you’re simply ready to retire, you can’t just exit your business overnight. You need a clear strategy so that you can seamlessly transition out of the business with as little stress as possible while maximizing your financial reward and legacy.


Start planning early

It may sound strange, but you need to start thinking about your exit strategy at the same time as you found your business. Decisions about how you incorporate, structure the company, secure financing, and even the benefits you’ll offer employees will all affect your ability to properly exit the business later on.

There’s another reason to start thinking about an exit strategy long before you think it may need to be implemented: You never know what might happen. A can’t-miss opportunity, great new idea you want to explore or personal circumstances (like a divorce or illness) could all put you in a position where you need to get out of the business earlier than you had planned. Having an exit strategy ready will make the process more enjoyable.


Know your options

You have various options available when it’s time to leave your business. While you may not have complete control over when and how you leave, you can make decisions today that will make it more likely that you’ll say adieu in the way you want. Your exit options include:

  1. IPO: For some ambitious entrepreneurs, an IPO is the holy grail — a sign that you and your business have truly arrived. Plus, it comes with the possibility of a huge payday. But an IPO is not for everyone. Your business needs to have significant market value, and you must be prepared to deal with sometimes onerous reporting and disclosure requirements, shoulder high costs, and give up the control you may have once enjoyed. Worse, IPOs can flop, and you may end up holding a bunch of shares that aren’t worth what you hoped they would be.

  2. Selling the business: As an exit strategy, a sale is less complicated than an IPO and allows you to cleanly cut the cord between you and the company while potentially earning a return on your investment. If you plan to sell your business, you must get an accurate business valuation from a business appraiser or broker before you plan to sell the company. Proper business valuation will help you make sure your sale price expectations are realistic. It’s not unusual for owners to overestimate the value of their business, even though statistics show that recently sold small business had a median sale price of just $180,000. Having an idea of your company’s value well before you plan to sell can also help you take steps to increase its value, such as making yourself less essential, so that a buyer knows that the business will thrive without you.

  3. Transferring ownership: Rather than an outright sale, you may want to transfer ownership to someone you’ve groomed to take over the business, like a family member, junior partner or your employees. If you want to pursue this strategy, it’s usually best to start preparing for a transition well in advance, so that you can gradually hand over responsibility as the next-generation leadership learns the ropes.

  4. Liquidation: If you can’t issue an IPO, sell your business or transfer ownership, liquidation may be your only viable exit option. You’ll probably get less than you would through an outright sale, but for some owners, liquidation is a perfectly reasonable strategy for exiting the business.


Exiting on your own terms

Just as important as understanding your different exit options is being able to identify the right moment for your exit. Like Kenny Rogers said, “know when to fold ‘em.” In fact, this can be one of the biggest challenges a business owner faces. Rather than waiting for the decision to be made for you, be on the lookout for signs that it’s time to exit the business, such as:

The economy and your industry are strong: If at all possible, you want to exit your business on a high note. If the economy is strong and your industry is growing, now may be the time to get out. Pay attention to market cycles and strike while the iron is hot. Finding a buyer willing to pay top dollar for your company will be easier when your business and the economy are flying high.
You’re ready for a new challenge: If running your business has become more of a burden than a passion, it may be time to step back. When you’re daydreaming about your next venture, avoiding the office, stressed because you feel you don’t have time to do the things you really enjoy, or dreading dealing with routine matters, you may need to put space between you and your business. In some cases, those feelings are signs that it’s time to embrace a new challenge.

Image Courtesy Practice Plan.

Image Courtesy Practice Plan.

You’re failing—but ready to try again: Not every business venture succeeds, and as an entrepreneur, you need to know when to cut your losses. If you’re not turning a profit after years in business, can’t attract customers and are losing top talent, your business may simply not be viable. Failure can be frustrating, but it is also a learning experience. Rather than sink more resources into a floundering enterprise, take stock of what you’ve learned and apply it to your next effort. As legendary entrepreneur Richard Branson says, “Failing doesn’t mean that you’re not cut out to run your own business … The key to bouncing back is to learn whatever lessons you can from the experience so that you can avoid making the same mistakes in the next launch.”

Proactive financial planning, both in your business and personal finances, beginning the day you found your company, will help make the exit process as seamless as possible. Consider the endgame as you make decisions, so that you can achieve both your business and personal goals. By taking charge of the situation from day one, you’ll be better able to exit your business on your own terms—and move on to your next big adventure. [4]


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References Sources:

[1] Taken from Entrepreneurship Is Like a ‘Choose Your Own Adventure’ Book written by Will Yakowicz  for Inc.

[2] Taken from Choose Your Own Adventure written by Christie Hall for Smallbusinessbc.ca.

[3] Taken from How ‘Choose Your Own Adventure’ was born written by Tommy Andres and Ariana Tobin for MarketPlace.

[4] Taken from Choose your own adventure: Exit strategies for entrepreneurs written by Jeremy Office for Chicago Tribune.

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