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Advice for Aspiring Older Entrepreneurs: Every Day Is Groundhog Day

By Delia Lloyd June 03, 2018 Managing Money

The writer and artist Austin Kleon has a great tip for how to stay creative: “Remind yourself that ‘Every Day is Groundhog Day.’”

The reference is to the Bill Murray film Groundhog Day, in which the main character wakes up every day to find that it’s exactly the same as the day before.

Bird by Bird

What Kleon means by this metaphor is that if you’re going to move forward on a creative project, you need to forget that there is a past or a future.

If you focus on the past, and regret what you’ve not yet accomplished, you’ll get blocked. And if you focus on the future, and all the next steps entailed in bringing your masterpiece to fruition, you’ll become paralyzed with fear.

In her famous book on writing, Bird by Bird, Anne Lamott effectively says the same thing. “Short assignments” is one of the ways she motivates herself – and her readers – to just keep going on their projects: start with a sentence, then a paragraph and then a chapter. Don’t try to take on the whole thing at once.

The Challenge of Starting a Business

But the groundhog day advice is also useful if, like me, you’re thinking of starting your own business later in life. Starting your own company is daunting at any age, but it can be particularly challenging for us so-called “silverpreneurs.”

After all, we’ve been around the block for a while. We feel the clock ticking more than the proverbial 23-year-old launching a start-up. We’re impatient to get going already.

Much like writing a book, however, getting one’s business off the ground takes time: You need to write a concept note, get feedback, and fine-tune it.

There are also the more economic aspects to consider: You need to research the competition. You need to set your prices. And how on earth do you save money for taxes?

If you’ve never done this before, there’s also a whole new vocabulary to master. Finally, there’s all that business development.

A friend of mine explained that 80% of his time is spent on business development; only 20% on delivery. He’s run a successful communications business for several years.

Even so, many days, it’s just about “Smile and Dial,” as he put it, pointing to the phone to indicate the amount of time he’d spent cold-calling that very afternoon.

I’m not Middle-Aged. I’m Zero.

All of this is fun and exciting, of course. I love new challenges. But the trick is not to get too freaked out about the past or the future as I build this new thing. If I think too much about the past, I’ll beat myself up for not having hit upon this business idea earlier.

If I worry too much about the future, I’ll start questioning the entire endeavour. I will ask myself, “Is there enough demand for this service? Will it pay the bills? Am I kidding myself about why I bring added value to this industry?”

I’m also worried that if I get too frightened to take a risk, I’ll go into “maker” mode, abandon my idea, and flee to to look at job listings.

So, as I go about this journey, I try to keep Kleon’s advice front and center: I’m not middle-aged. I’m zero. Happy Groundhog Day.

Are you an aspiring entrepreneur? Have you considered starting a new business in your 60s? Please share your tips and insights on how you made it through the initial stages of setting up your own venture.

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The Author

Delia Lloyd is an American writer and communications consultant based in London. Her writing has appeared in outlets including The New York Times, The Washington Post, The Financial Times, and The BBC World Service. She blogs about adulthood at and is a visiting fellow at the Oxford Institute of Population Ageing. Follow her on Twitter @realdelia.

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