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When You Think You’re Ready to Jump Off That Entrepreneurial Cliff, Think Again!

I thought I had it going on.

I’ve held marketing management positions in the technology industry for 25 years. I know how to take the complexities of technology and make them easily understandable and relevant to businesses. I’ve established an excellent reputation, am well respected and have a deep network of business colleagues that I’ve kept in touch with throughout the years. I have worked for large, well-known Fortune 500 companies and small start-ups. I know how successful businesses run and have been hired because of my expertise to help companies grow.

With all of this experience, I could certainly start my own business. Right? Sure, it would be a lot of work but I’ve done that work at other companies and it’s about time I do it for myself. I have my plan. Now it’s time to jump off that proverbial cliff and execute it.

Pie in the Sky Entrepreneurship

Starting a business wasn’t something that just came to me one day and I decided to give my notice to my employer the next day. It was something that I considered off and on for years. Certainly, with all of my experience and the amount of time I had spent assessing every good and bad thing that could possibly come my way, I was ready. I had answers, solutions, and workarounds for every eventuality. Or so I thought.

In 2014 I took the leap and became an entrepreneur. My plan was that by the end of the first year I would have enough clients to warrant two full-time employees, I would have a number of contract employees who would work for me on specific client projects and the company would be making a profit.

What I didn’t factor in was that I would have to become a salesperson, an HR executive, a business attorney, a marketing professional, a CFO and an office manager all at the same time and what that would mean to the speed with which I could promote my business, bring on new clients, make money and grow.

Over the last two years, the thing that has surprised me the most is how long it actually takes to build a profitable business. For example, the number of meetings you have to have with a company before they become a client. How long it takes to build back-end technology to support your business operations. Finding the right people to work for you. How slowly large corporations move when making decisions on projects you have discussed with them for months. Of course, having spent many years in the corporate world I already knew these things but it’s a different story when you are the one responsible for all of it.

The Trough of Sorrow

Your Entrepreneurial Dream

Do you have a dream of being an entrepreneur and starting your own business? Well here is some advice. When you think you’re ready to jump off that entrepreneurial cliff, think again. I don’t mean to say that you shouldn’t do it. My recommendation is that you work as hard as you can at your dream while continuing to work at your current job. Here are 7 recommendations for you to follow:

1. Money is the foundation.

It’s no accident that money is the first item on this list. Understand that your expenses will grow and your savings will shrink at lightning speed.

Stay at your current company and put as much of your paycheck as you can into a separate bank account. Live frugally – stop going to Starbucks, cancel your cable television subscription, bring your lunch to the office, sell the second car and tell the lawn service you will be cutting your own grass.

Do you have a working spouse? Great. You should both live on one salary and bank every bit of the other salary.

Remember two things:

  • Banks and investors will not give you money if you don’t have any customers so expect to have to finance your business on your own for the first 3-4 years. Do you have enough money to both grow your business and eat, pay the mortgage and live for 3 years? If not, stay in the job that you have and stash away every dollar that you can.
  • Your expenses will grow faster than your business. Building a website, hiring a lawyer and accountant, developing a product, designing your logo and signage, buying computer equipment and hiring someone to fix it when it breaks, all takes money. Remember, this is money that must be handed out before your first customer ever pays you.

2. You don’t have to go it alone.

Being an entrepreneur, often working out of your home or a small co-working location, can be very lonely. In addition, entrepreneurs who stay at their corporate jobs while working on their business often keep it a secret from their current employer and co-workers for fear they will be fired.
But it is important to get the encouragement you need to keep moving ahead with your plans. Is there someone you trust who understands your business and your industry and could become a mentor?

You can also gain insight, share knowledge and receive advice from other entrepreneurs by joining Meetup networking groups, LinkedIn start-up groups and Twitter discussions on entrepreneurship. Local in person events and group meetings are great but don’t forget that the Internet has enabled entrepreneurs from around the world to also connect and build relationships online.

3. Run in stealth mode.

Some companies are not happy about their employees having side jobs, especially if they think that you might be doing it on company time. They will most certainly go online to look for a website, written content, or anything else with your name on it to see if you may be involved in a new business. If this is the case, you should run your business in stealth mode for as long as you can.

For example, when building your website it is important to include an About Us page, even if you don’t want to reveal your involvement. (The About Us page is one of the four most visited pages on any website.) Unlike many About Us pages that include names and photos of the management team, you can create a pen name to represent yourself as the person running the business. You might want to call yourself the Fashionista, the Marketing Advisor, the Hospitality Host, the Financial Sage. Create a name that is appropriate for your business and industry and use it on your website and in email communications.

You can also create an email address like [email protected], [email protected] or [email protected] which customers can use to contact you instead of using your actual name.

4. Have potential clients waiting in the wings.

Get to know as many people as you can in the industry in which you will work. This is easy if your new business is in the same industry as your current company. Developing a good reputation and long lasting relationships will help your business get out of the starting gate more quickly.

Never burn bridges. You don’t know where people from your past will pop up again and they could make or break you.

When I decided to take the leap into entrepreneurship, I reached out to colleagues and friends in the technology industry letting them know that I was leaving my current position and explained what my plans were. Because of the relationships I had built, some contacts immediately said they wanted me to do work for them.

The news of my plans also spread to firms I had not worked with for years and they reached out to me to chat about possible opportunities. The fact that I was able to immediately put together a small group of clients helped to sustain me in the first year of business.

5. Set specific goals and deadlines.

Juggling a day job, a side business and a personal life can be daunting. When trying to decide which one you should focus on first, the day job and the personal life will usually win out. As a result, the entrepreneurship goals and dreams you carry around in your head never come to fruition.

Write a business plan which includes specific goals and deadlines that will enable you, if accomplished, to quit your day job and follow your dream. Attach measurable actions to each goal and have a mentor, peer group, or close friend hold you accountable for achieving those goals by the deadlines you have put in place.

Break these milestones into smaller, bite-size projects or tasks so they are more easily attainable. Whether it is a small task like creating and buying your business cards or a larger project like designing, writing and launching your website, every goal you achieve and deadline you meet provides you with an ever increasing sense of confidence in yourself and brings you closer to the day when you become a successful entrepreneur.

6. Passion will sustain you.

Setting specific goals and deadlines is important but if the passion for your new business is gone then the chances for your success are slim. After 8 to 12 months of working on your new business while still at your corporate job, ask yourself, “do I still have as much passion for my new business as I did when I first wanted to jump off that cliff?” If you do, keep going. If you don’t, consider if this road you are on is really right for you.

Remember, you are still giving 100 percent of your effort to your day job and working on your new business at night, early in the morning, on weekends, and any other time you have available. After 8 months of doing both, do you slink home at night and want to flop on the couch and watch TV or do you want to rush home to uncover new opportunities or jump out of bed 2 hours early to complete those items on your to-do list?

7. Hiring employees.

Believing that you have to hire full-time employees right out of the gate will quickly drain your bank account. There is an alternative. Freelancers are the fastest growing portion of the labor market and have come a long way from the traditional “temp” employee that we remember from 10 or 20 years ago.

Today’s freelancers are well educated, have many years of experience, and include attorneys, accountants, marketing executives, management consultants, start-up specialists and more. Hiring freelancers to complete specific projects or provide strategic consulting services enables you to take advantage of qualified professionals, paying for only what you need and nothing more. When the job is done there are no additional expenses and the outflow of cash from your new business stops immediately.

Best of all, technology like Skype and other video messaging tools enable you to hire and easily communicate with the most qualified workers, whether they are across town or across the globe.

18 Mistakes That Kill Startups

The Bottom Line.

So, did I do the right thing? Am I happy I jumped off the cliff and started my own business? Yes. But, had I known then what I know now, I would have stayed longer at my corporate job and gone much further in the development of my business before leaving.

My advice to you: Take some time to sit down in a quiet place and honestly evaluate your readiness – your personal needs, financial needs, and business goals. If you are truly passionate about this business, you will have the drive to build it while you are still at your current job. Then leave at the appropriate time. You will know what the right time is when it comes.

It’s important to remember that those companies we hear about who have achieved overnight success are not overnight successes at all. It has taken years for them to become household names.

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