Defensive Entrepreneurship: A Strategy for Succeeding in Business and Life

Create a structure for falling back on a plan B, C, and D

“What kills me is that probably everyone working at our local Walmart has multiple skills that could earn them more per hour than working there. And they keep developing more valuable skills (auto repair, carpentry, sewing, canning, etc.) over time to help them afford working at Walmart!”— my sister who lives in southern Indiana

When I started my first publishing company, I learned the trade from the pub-forum list, an active email group of 800 people in the world of independent book publishing. (It was the mid-90s, so we had the benefit of this amazing new concept.) One of the longest and best threads I remember was the importance of having a skill other than book publishing to fall back on — “a real skill…one that people will always pay money for.” Bartending was cited frequently. So was cutting hair.

When I first had this conversation with my sister and the experience on the pub-forum I hadn’t yet heard the term defensive entrepreneurship, but it’s relevant in both scenarios. In the first, Walmart employees have some defensive entrepreneurship structure already built but may not be aware of it. In the second, a notion of defensive entrepreneurship was encouraged as an essential piece of being a book publisher! It was partly tongue-in-cheek, but I took it to heart in the way I ran my company and what I put into place in the background should I ever need it.


What Is Defensive Entrepreneurship? Many references to defensive entrepreneurship refer to a defensive way to practice entrepreneurship, meaning the main business someone is currently working in. What I’m referring to is entrepreneurship in its broadest sense — an enterprising approach and/or some type of business endeavor — used as a defensive strategy in your life. A means of protecting oneself, covering your behind, of fighting back against circumstances.

Defensive entrepreneurship doesn’t just give you options in the face of emergencies. It gives you options period. The freedom to quit. The freedom to slow down. The freedom to hit bumps in the road of life. And it offers something quite the opposite of disruption: peace of mind. Freedom from worry. A solid confidence in the back of your mind, deep within, that makes everything better. No matter what happens, you’ve got this covered.

Defensive entrepreneurship may involve having a skill you can bank on tomorrow if needed or a business in the wings you can rev up in a week, but it’s more of an overall strategy of redundancies and having a safety net that’s feels like a ginormous safety pillow. Review these components I have for myself and have seen in others. See how much you already have in place that you may not be aware of, what areas you could bolster quite easily, and where you might work on shoring up over time.


Cushion For security and unexpected situations, nothing beats the classics of money in the bank and insurance. Savings. Emergency funds. Investments. Equity in a home. Retirement accounts you shouldn’t dig into unless you have to. Gold in the backyard (or whatever). Insurance for all the things. The fact that this type of cushion can be harder and harder for people to put into place is also a demonstration of why defensive entrepreneurship is so critical. A cushion is cushy.

A Day 1 Go-To A Day 1 go-to is something you can do immediately in a cash crisis moment to put yourself on the fast track to bringing money in and to ease your mind about what kind of acute situation you’re in.

Years ago, one of my cousin’s husbands posted on Facebook: Just lost my gig and don’t have another one for three weeks. Does anyone need the inside or outside of their house painted before then? We happened to need our entire condo painted and within three days he and his bandmates had finished the job. My brother has maintained a longtime

relationship-turned-friendship with a placement expert at a temp agency. In between jobs, she has been his Day 1 go-to. What’s yours?

Internal Strengths Various mindsets and personal characteristics support a defensive entrepreneurship foundation:

  • Confidence and boldness. I got this. I can do it if I have to. I will do it.

  • A mindset of alternatives. There are many ways to live, to work, to make money, to address my concerns.

  • Creativity. I can always count on my creativity to generate enough ideas and solutions.

  • A growth mindset. I can and will learn what I need to in order to get through this.

  • Personal responsibility. I can’t control everything, but I am responsible for doing what I can with what I have from where I’m at.

  • Asking for help. I don’t have to do or know or have or be everything. I can count on others and ask for what I need.

  • Grit and resilience. I will prevail.

  • Choosing yourself without being only for yourself. To quote Hillel the Elder: “If I am not for myself, who will be for me? And being only for myself, what am ‘I’? And if not now, when?”

Network Tend to your network in ways that will fortify you through stormy times.

  • Strong ties. Maintain and nurture your relationships with family and friends, those you love and like the most.

  • Weak ties. Stay in loose touch with a wider range of people — such as through Facebook and LinkedIn online; community, social, and professional events in person. It is through weak ties that most jobs and new opportunities are found.

  • Grow your network. Continue to grow your network in ways that make sense for you. Best way to be memorable when meeting new people? Activate your curiosity and ask others all about themselves.

  • Reminders. Remind others of ways you can help them when you’re not in a desperate situation. For instance, musicians who also paint interiors can drop that in conversations from time to time so that others know it’s always on the table.

  • Offers. Get in the habit of proposing your usefulness to others in your network, even when you don’t need a job or an opportunity. It sounds like this: If you know anyone who needs someone who can x, feel free to share my name. Or, I’m always open to opportunities to do x, y, or z.

Lifestyle Matters Know in advance the adjustments to your lifestyle you would consider in a financial crunch — small and big, near-term and long-term. What luxuries would you cut out right away? Where else can you reduce your spending? Do you have anything or lots of things that can be sold pronto for a needed burst of cash? Could you, would you sell your car? Your home? At what point would you leave your rental? Get a roommate? Who all might have an extra room, a basement, or a coach house where you could crash, and for how long, if things got desperate? Would you live in your van? A campground?

Some of these things may seem extreme but hard times, very hard times, happen to real people every day. Thinking through dire scenarios in advance offers real solutions and psychological resilience should they ever come to pass.

Skills As the publishers asked way back: Do you have any skills, real skills, that people will always pay money for? Do you also have the skill of and temerity for informing people of your skills for hire? If you’re handy, can you put a flyer up on community bulletin boards? Will you post your availability on Craigslist? Will you go from fancy hotel to high-end restaurant to corner bar in your town to see if they need a bartender?

If you’re stumped or need more ideas and ideas you may find appealing read this for inspiration: Tap Into Who You Are and Bring What You Have to the World: 8 ways for authors, creatives, side hustlers, solopreneurs, and micro-businesses to customize and optimize their marketing efforts.

Freelance Do you have freelance options you can always rely on? An Upwork profile? An account with a temp agency? A database of satisfied past customers to contact? Knowledge of just how many marketable skills you have and what sort of clients pay for those? My hands-down favorite advice in this category is to take Diana Schneidman’s 1,000 phone calls in 30 days challenge. Keep on dialing until you get the work you need.

Microbusiness Is there a little business you could get up and running in a short amount of time if you absolutely had to? Do you have the skeleton of an idea and the resources to implement it? For myself, I keep an ebay account idling in the background that I throw a handful of hours at each month and make $200–$300. Further up the ladder, I have a hobby business that I do about 30 hours a month that I could start taking seriously if I ever needed to. Do you have or could you have or do you need a microbusiness humming in your defensive entrepreneurship strategy?

Action Plan Knowing you have a plan in place if you ever need or want it goes a long way in creating for yourself the ongoing freedom an underlying sense of security provides. For myself, I have all of the above in place, and I also know that I could take action in even unlikely eventualities. What if the financial system collapsed and our savings disappeared? What if a natural disaster forced us to move for months? What if I found myself alone and caring for my son? I know I could rely on myself and use the knowledge in this article to create and start a plan in minutes.

See the specific Day 1 action plan I suggest for authors, writers, and similar creatives if they need to make a full-time income from their craft starting tomorrow.

The AWE Question Finally, as you establish your defensive entrepreneurship infrastructure, ask yourself from time to time The AWE Question from Michael Bungay Stanier’s The Coaching Habit: And What Else? What else can you do to feel secure? To build your defenses? To fortify your life? If you take to the above things in a way that makes sense for you, you may very well reach a point where you realize: Nothing else. I’m good.