I always loved the idea of being an entrepreneur. But like most normal people, I started my career as an employee. I worked for my first employer for 10 years. I worked for my next employer for 9 years. I liked my jobs. But I always knew that in my dream scenario I wanted to own my own business. I bet your dream scenario has a similar entrepreneurial ending. And maybe a swim-up bar.
After years of semi-scientific research, I have concluded that there are 3 great times to start your own business. I have published my findings below for your evaluation.
The 3 Great Times To Start Your Own Business.
- When you are first out of school, and have nothing to lose.
- When you retire, have plenty of money and time, and have nothing to lose.
- When you are 40ish, have a lot of experience, skills, contacts, and confidence. And a lot to lose.
The first 2 paths are popular for obvious reasons. Like the-nothing-to-lose part. When you are right out of school, you aren’t giving up anything. And at the end of your regularly scheduled career, you get to choose an overtime period. Which is fun. And only threatens your shuffleboard time.
But how in the world do you switch from the employee track to the entrepreneurial track mid-career? Even more challenging, how do you do it if you have a really successful career and are well compensated? How do you make the transition when you have a significant mortgage? And car payments? And kids? And a spouse you really want to keep? Plus, there is the insurance thing. And the annual company Christmas party with all the free alcohol! How do you walk away from all that gravy?
You can do it!
Well W-2 Nation, I did it. And it has been an amazing experience. When I turned 40, I realized that if I died then and there, on the dance floor, while doing the Electric Slide, my greatest regret would be that I never started my own advertising agency. So I resolved to start my own business within the next 2 years.
I launched The Weaponry, an advertising and idea agency, 6 years ago. Today, we have 26 clients, 2 offices, health insurance, dental insurance, and a matching 401(k) plan. (Never forget the k, or all you have is an area code.) We are looking at a 50% year-over-year revenue growth rate. And most importantly, I got to create the dress code.
Now, I want to help you begin your mid-carer entrepreneurial adventure. What lies below the fold is the collection of tips, how-tos, and advice I wish I had 7 years ago. This isn’t how-to-build-a-unicorn stuff. I’m not talking about a Zuckerberg, Gates, or Jobs path, where you drop out of college and start a trillion-dollar business. I am talking about advice for regular people, with regular careers, who want to use their experience as a launchpad to entrepreneurial success.
That’s what I did. And you can too. Here’s how, brown cow.
20 Key Steps To Becoming A Mid-Career Entrepreneur.
- Surround Yourself With Entrepreneurs. Entrepreneurship is a mindset more than anything. It helps to spend as much time as you can with other entrepreneurs. It helps rewire your brain to see opportunities and become a problem solver. It will help you develop your risk tolerance. Because once you are around entrepreneurs who are enjoying the rewards of their risk tolerance you will realize the nice homes, cars, vacations, and freedoms are well worth the wager. Ask your Mentorpreneurs all the questions you can think of. They will want to help. And by hanging with your Mentorpreneurs, you realize it is far riskier to leave the control over your income to someone else. Plus, you quickly realize that you can create anything you dream up. Like the word Mentorpreneur.
2. Become really great at what you do. When you are great at what you do you become sought after. And when people seek you out, it means you no longer need your employer to develop opportunities for you. Because you can create those opportunities for yourself. This is called career capital. The more you develop the easier it becomes to call your own shots (shots shots shots!) When your clients at your day job are more in love with you than the company you work for you have a green light to start your own business. And green means go, Mario!
3. Develop And Maintain Your Network. People work with people. And they love to work with people they like and trust. Continuously expand and strengthen your relationships. The more people who like and trust you the better. Those people will become customers, partners, connectors, and referrals. And those are the 4 most important people in an entrepreneur’s life. (After the supportive spouse and great coworkers.) If you’ve neglected this area of your career, it’s time to get to work. When I started The Weaponry I quickly realized I had done much of the hardest work of entrepreneurship decades earlier through my relationship-building.
4. Save Your Money. By having reserves in your bank account or investments you can tap into, you buy yourself running room to start your own business. Most people can’t consider starting their own business because they don’t have the luxury of not having a dependable paycheck for several months. Don’t be that kid. If you don’t have the money on hand yet, start your Run-My-Own Business Fund today. You might not need the money. Or not much of it. But simply having it available provides the confidence to jump, like David Lee Roth.
5. Live Below Your Means. As your income increases, don’t let your expenses rise at the same rate or you will always need your current level of income. That’s a problem. You’ve heard of the golden handcuffs of a high-paying job that keep people locked into their employer. But the most dangerous career situation is the one where you need your current income level to support your lifestyle. Because you will never be able to downshift into a lesser-paying situation, even temporarily. And the first move an entrepreneur needs to make is downshifting into a lesser-paying situation for an undefined length of time. That is the price of entry. That is the entrepreneurial initiation ritual, my friends. Tip #4 helps you bridge that gap. My dip only lasted about a year. But it really made me hustle. And hustling helps you make money. #dothehustle
6. Don’t Quit Your Day Job. To combat the money challenges outlined in the previous points, don’t do something rash, like quit your job. Hold onto your job as long as you can. It will be the primary source of funding for your startup. Use your current job to help pay for the expenses of your next job as long as you can. Work on your startup at night and on the weekends. Like Shania Twain said, no one needs to know right now. Not quitting your day job allows your startup to gain speed, momentum, and cash flow. Not quitting until you have to makes it much easier to jump from the Employee Train to the Entrepreneur Train. If we were swinging from ring to ring on a playground, think about not letting go of the ring you are holding until you have your hand firmly on the next one. And if you never have a firm grip on the next ring, then you never let go of the one you were already holding. No harm. No foul. You tried. You can be proud of that.
7. Read The Book The E-Myth by Michael Gerber. This book is the bible on how to start and run your business the right way. (Only there is no Jesus.) I followed all of the guidance in this book before launching The Weaponry. It helped me think about the whole process the right way, and avoid a lot of problems. When people tell me they are planning to start a business, or are floundering in their startup, I always recommend they read this. And everyone always thanks me. If I were you I would hit the link above and order the book right now. Tip #8 can wait.
8. Create Your Legal Entity: It’s easy to create a legal business entity. Start simply by applying for your FEIN. Which is your Federal Employer Identification Number. It’s like your business’s social security number. This ID number enables you to do everything the way the government and IRS want you to. With this in hand, you can file your legal business entity with your state as an LLC (Limited Liability Company), Corporation, Limited Partnership, General Partnership, or as a Sole Proprietor. I set up an LLC. (Yeah you know me.) It’s quick and easy. Then you can open your business bank accounts and get your company credit card. With these things in place, you have your financial and legal structures ready to roll. Which means you won’t need to ask your customers to pay you in cash. Or chickens.
9. Get Quickbooks. Quickbooks is the accounting software that makes it easy to track and manage your accounting. You connect all of your bank accounts and credit cards to this. It makes it easy to create and send invoices (bills) and to know what is due and when. It also provides reports (profit and loss, profitability, balance sheets, etc.) and dashboards that help you manage your business. Get this going as soon as you can afford to. It will become the backbone of your accounting system. And your scoreboard. Best of all, Quickbooks is not the book equivalent to quicksand.
10. Get A Good Bookkeeper. Bookkeepers are God’s gift to entrepreneurs. They are reasonably priced specialists who have a valuable skillset that you likely don’t have. They can help you stay on top of your accounting while enabling you to spend more time on the things only you can do. Like finding paying clients. And putting on your deodorant.
11. Collect Recognizable People And Logos: You can start your business by working with anyone. But the goal should be to collect recognizable names as customers. That could mean that you work with well-known brands or people that other people know. When you share the kinds of brands or people that you work with you are elevating and legitimizing your brand by using theirs. If you work with individuals, work with the most popular most trusted, and most respected people you can. Their decision to work with you will carry more weight than say, your grandma. Sorry, Grandma.
12. Get involved in your community. The more involved you are in your community the more you will be connected to others and the opportunities they can introduce you to. You could be involved as a volunteer, member, attendee, or sponsor. You are going to want strong ties to the people around you and this is one of the best ways to get to know as many people as possible. Even better, when you support your community you will find that your community supports you too. It’s a thing.
13. Grab Chocolate Milk. Entrepreneurs understand the power of spending time with other people. Getting together for chocolate milk, (my preference) or coffee (most of America’s preference) is not about the beverage. It’s about the sharing and comparing of experiences and ideas. Through the process is sitting down with another person and talking you discover new ideas and resources. It creates a great transfer of knowledge and experience. It is the best way to tap into another person’s perspective and network. You could also meet for breakfast, lunch or drinks. Or fricken caramels. It’s all ah-bu-trary. #namethatmovie
14. Start A Blog, Podcast, Or Regularly Published Knowledge Share. It is not about who you know. It really is about who knows you. The more people who know about you, what you know, and what you are doing, the better. I started a blog right when I launched The Weaponry. And it has been a great vehicle to share my thoughts, ideas, successes, and learnings with the world. By doing so, my business and I are both top of mind when people have relevant opportunities. Podcasts, newsletters, columns, and social media channels all work too. The key is to share information and value with the world broadly so that more people than you could reach through individual messages know about you, your skills, philosophy, and eventually your business offering.
15. Find a supportive spouse. In the middle of your career, you are likely to have a spouse or life partner who is tied to your success or failure. Their support and encouragement are critical to your success. My wife Dawn has been amazingly supportive. She never batted an eye or raised an eyebrow when I shared my entrepreneurial vision with her. I would share this post with your partner so that they have an idea of what you are trying to do. That way they can help and support you as much as possible. If they are not supportive you have an important decision to make. And that’s all I have to say about that.
16. Read Read as much as you can about business ideas, successful companies, leaders, and entrepreneurs. This is the greatest entrepreneurial hack there is. Learn all you can from others who you admire and want to emulate. Read about how other Founders did what they did. There is no end to what you can learn from others. Read books, online articles, and blogs. Listen to podcasts and audiobooks as you commute. Drink that knowledge in. Create your own curriculum. And give yourself your own, self-directed advanced degree. You can even walk across your own stage and hand yourself an official-looking piece of paper. That would be weird. But you could do it.
17. Grow Your LinkedIn Connections. LinkedIn offers the best measure of your network. Create a profile if you haven’t already. Become an active user. Add everyone you meet to your LinkedIn profile by sending a custom invitation reminding them of how you know them or why you want to connect. This will become ground zero for raising your profile and staying in touch with your broader network and the opportunities they bring. Like, comment, and share content from other people. Make people who don’t know you curious about who you are. Insider Tip: LinkedIn offers an audio icon next to your name that let’s you share how your name is pronounced. Click on mine to see how it works.
18. Learn As Much As You Can About The Business You Are In Now. While you are still employed by someone else, take advantage of the experts in the organization. Learn from the finance or accounting teams. Talk to HR about how benefits, recruiting, and reviews work. Talk to sales about how they generate leads and close deals. Talk to operations about what makes them such smooth operators. Talk to IT about, well, IT. You can learn about all of the things you are going to need to know as an entrepreneur while in your current job. Think of it like studying. Your coworkers will love your interest in their work. And they will be flattered when you start your own business and credit them as your sliver mentor in their specialty. You’ll also know who would be a good resource to hire after your non-compete clause expires.
19. Write down your plans. It’s one thing to think about starting a business. It’s another to write down a plan to make it happen. Once you have a vision for your dream business, write it down. The more details the better. That written plan becomes your blueprint to build it for real. I followed the written plan approach from The E-Myth, and it gave me great structure and clarity around what I was creating. Do this too. Also carry notebooks. Not only are they great for capturing spontaneous ideas, but if you get shot in the notebook, it just may save your life.
20. Talk To Former Clients About Your Plans. Your best prospective future clients are your past clients. When I launched The Weaponry I discussed my plans with several former clients. Within the first week of discussions I had 5 clients tell me that if I created a business they would send work our way. That confidence, interest, and demand in my offering made it much easier to jump. 4 out of those 5 former clients became future clients. The other one is living with constant regret. Right Chad?
Starting your own business in the middle of your career can sound intimidating. But the more you know, the easier it is. You can do it. Utilize the knowledge of those who have gone before you. Most of it is easier than it seems. With the tips above (that I wish I knew when I was starting out) you will be able to start taking steps today. Then simply never stop. If you need a Mentorpreneur, just reach out to me through Linkedin. Tell me I sent you.
*If you know someone who wants to start their own business and could benefit from this message, please share it with them.