Self-Employed? 11 Reasons You Should Try All the Things


There’s more to business success than niching, focusing, and maximizing


“Have no single point of failure. Have no single path to success.” — James Clear

Niching, exquisitely-wrought branding, hyper focus, and the strategic optimization of every minute, every dollar, are reasonable and effective ways to run and build a business or solo empire. But I resist those things for the most part even as I have relied on discipline, ongoing learning, productivity hacks, and long-term thinking as routes to sustainability and peace of mind in my own 35 years of business ownership and self-employment.

After all these years, I learned and adopted a name from author Barbara Sher during the pandemic for my style of business: refusing to choose. Instead, I am open to ideas and possibilities, consider every avenue, want to meet all the people, and want the freedom to try all the things without the permission or approval of the business pantheon. Here are some of the reasons I see to take this approach.


To practice defensive entrepreneurship Having multiple irons in the fire builds a Plan B, C, and D into your business model. Those options can provide the needed cushion and security that allow you to take risks, take time off, work at your own pace, explore things that catch your heart, and sleep comfortably at night.

To test options Sure, this refers to the A/B testing of headlines and sales pitches and color schemes, but it’s broader than that. It’s trying out a number of things, sometimes at once, sometimes sequentially, because you don’t always know what’s going to take off or why or in what directions and with what new benefits.

To launch multiple products and services Experimenting with options and chasing random threads can lead to more products and services than you originally planned. And those may open up new customers, income streams, spin-offs, and opportunities.

An extra I know on multiple TV shows built an Etsy business selling drop-shipped products to fans of those shows when he discovered that none existed to give his family and friends. An author I’ve worked with turned her expertise and charismatic personality first into paid speaking events and workshops, then a tour series, and then a tour business. The one-hour tours became overnight tours and the growing fan base turned into an annual conference.

To take advantage of opportunities that crop up Don’t let single-minded focus on a plan, your money-maker, or your comfort zone get in the way of taking advantage of unexpected opportunities that show up on your doorstop.

To expand your network Bruce Springsteen teamed up with Barack Obama in 2021 for renegade podcast conversations. James Patterson and Dolly Parton joined their best-selling forces to write a novel together, Run, Rose, Run (March 2022 release), with a companion Parton album of the same name. Sarah Palin and Rudy Giuliani connected their way to Masked Singer appearances. Life is good, surprising, and productive when your network is big. An ever-expanding network means advice, companionship, sounding boards, feedback, referrals, ideas, mutual support — and the new creativity, opportunities, and relationships that spring from it — are just a text, email, phone call, or synergistic collaboration away.

To leverage a spectrum of resources And, speaking of your network: In Focal Point, author Brian Tracy emphasizes the multiplier effect of leveraging seven specific types of resources other people have: their knowledge, their energy, their money, their successes, their failures, their ideas, and their contacts. This is not about taking advantage of others, it’s about the complementary two-way gains that come from interacting with fellow humans. Join organizations, attend virtual events, make a habit of reaching out, and set up coffees, lunches, drinks, and walks with a range of others.

To learn about yourself Self-employment and small business ownership are accelerators to self-awareness. The challenges, triumphs, disappointments, responsibilities, and unpredictability of being so in charge of your own income make it hard to avoid for very long facing the firestorms and nuances of emotions, one’s failures and shortcomings, the differences between oneself and one’s persona.

You will also come to know your strengths, abilities, creativity, resilience, and values. Out of the pandemonium a new you and new discoveries are forged. I know a musician and liberal arts type who realized she had a way with numbers, projections, and the hard calculations of business; an introverted technologist who discovered that he was good at sales and enjoyed teaching most of all; a hard-driven designer and salesperson who most valued the patience he had acquired along the way.

To develop skills Trying all the things requires developing new skills and mixing-and-matching existing ones in different strengths and hues. And that’s a good thing. More skills, more better. Learning new things stretches our brains and ossifying boundaries; reduces the stale, ups the bandwidth. Non-literary skills I developed owning a book publishing company — including warehousing and order fulfillment, print buying, project management, contracts, negotiation, accounting, and coaching — have all been put to use for multiple consulting clients.

To challenge yourself Pursuing new and difficult things is another bonus of being the boss of your workday and another way to incrementally build up, or quantum-ly leap, to new successes. Some of the ways I’ve challenged myself over the years — cold calls and public speaking — are still challenging, but I persist with my baby-steps improvements in these areas. Other challenges, such as making on-the-spot proposals, asking for the business, managing bigger projects and bigger budgets, and navigating so-called crisis situations are examples of things that over time became easy and normal for me and allowed scaffolding to bigger and better exploits.

To cultivate your interests Because I want to. Because I’m curious. Because I’m interested in that. These are all splendid reasons to move from the hyper focus of goals to the fuzzy calculus of hobbies and delights.

To engage in Slow Business Because, what’s the hurry? Being self-employed is in part about you, your freedom, your personal expression, and your life. Take the time to do it as it makes sense to you, become a practitioner of Slow Business.