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The Late Entrepreneur: Starting My First Business After 40

The Late Entrepreneur: Starting My First Business After 40


Most of my co-authors on this project wanted to be entrepreneurs from an early age. I didn’t. Many of them as kids probably had lemonade stands or similar. I didn’t. Truth is, I wanted to get a good job and be well paid. Running my own business came much later.

From a young age, I understood the value of money and working. During my schooling in Canberra, Australia, I worked doing gardening jobs, a milk run, and pumping petrol. After finishing school, I specialized in jobs starting with “D” including working as a drummer, a diplomat, a developer and a drug pusher (don’t worry, I mean pharmaceutical industry, not street corner).

So, why after these interesting and well paid jobs (especially the latter ones) did I finally decide to take the plunge and run my own business?

I think turning 40 was a factor (maybe it was the karaoke at my 40th!). I realized I was capable of more than just working to build someone else’s business. I was doing a lot of personal development—reading books (like this one) and attending seminars. Somewhere I heard someone say: the enemy of a great life is a good life.

This really got me thinking. Why live a good life (which I was doing) when I could live a great life?

After a lot of thought, I decided starting my own business was the most effective vehicle to get what I wanted: to make a difference and leave a legacy, to live a great life. So in 2014, I established my own marketing company, helping dentists market their services. If you’re 40+ and looking to make the leap, these are four things I wish someone had told me before I started.

1. Take care of yourself and get connected

Something that caught me completely by surprise when starting my business was the potential toll on my mental health. My family will tell you I’m a fairly level person. Yet this journey has been more of an emotional roller coaster than I can ever remember. I’ve wanted to quit many times. There’s been high highs and low lows. I’ve:

  • made $10,000 in one hour (high high)
  • had a client tell me that he was leaving, and had discussed my business with my other clients and they weren’t happy either (low low).

In business, you may have less social contact than you did in your job. I spend most of my time working from home, communicating electronically with my clients and team.

With this in mind, building a network is really important. Give people a call occasionally just to see what’s up. Hanging out with other entrepreneurs is really helpful too (check out Entrepreneurs understand the stresses that come with running your own business and can provide an excellent source of ideas and support

2. It’s all down to you

As an employee, your job likely comprised only part of the company’s activities. No one works in sales, operations, finance, and HR all at the same time. Yet for your own business, you’re responsible for all of those functions—even the ones you hate. As a sales/marketing guy, the idea of handling operations enthuses me as much as cleaning out a septic tank. Yet take care of it I must. Outsourcing can help a lot but until the money starts rolling in, you may be limited in what you can afford.

Be aware also your former organization probably had standards and policies in place that were necessary for that business (and normal for you) but may be completely unnecessary for your new business. You get to set what’s normal now!

3. Needs and wants

As an employee, I had access to all sorts of cool stuff – an expense account, a company car, etc., with no concern for the cost. But now that this is your business, you’re going to need to pay close attention to your costs because you’re paying for them.

One thing I really liked having was Qantas Gold Frequent Flyer status. I got access to an airline lounge, priority seating, faster check in, etc. But this higher class of travel comes at a cost. After starting my own business, I basically spent my profit for two months by travelling as I had when I wasn’t paying.

Have a close look at what you really need as a business owner versus what you’ve been getting courtesy of your old employer. You’re not in Kansas anymore, Dorothy.

4. Show me the money

Anyone starting their own business should be pretty clear that there are going some lean times financially, especially at the start. No surprises there. But if you’re a 40+ first time entrepreneur and a long-time employee, there’s something else you need to consider.

Chances are you have a family, a mortgage, and/or a range of financial commitments. What all of this adds up to is an established expectation about your quality of life. Where before you may say something like, “In our family, we eat out once a week, go on nice vacations, etc.,” your move into entrepreneurship may just put that lifestyle on hold for a while.

To soften the blow, discuss your plans with affected parties, and have a close look at your financial commitments. What costs can you put on hold? How are your financial reserves for handling the mortgage? How will your other half feel about less money coming in?

So what now?

While there are challenges, starting a business after 40 isn’t all bad – far from it:

  • You have life experience that 20-somethings lack
  • Your self-awareness should be better than ever
  • You know what you’re good at and what you’re not—what you like, and what you don’t.

With these insights, your chance to build a business and live a great life awaits, no matter your advanced age. Go get ‘em, tiger!

Interested in reading 99 other stories just like this? Grab The Better Business book here.

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