July 6, 2021

12 Entrepreneurial Truths Working Parents Should Embrace

Article by Daisy Dowling

You’re a working parent or planning to become one. More challenging still, you’re an entrepreneurial parent or planning to become one. And you’re feeling daunted, conflicted, exhausted — or all three — by what you’re going through or what lies ahead. You feel like you’re all on your own.

How could you not?

Each parent walks their own path. Each entrepreneur is on a unique journey. No two self-employed parents, or parent-entrepreneurs, have identical experiences.

Even if you and your next-door neighbor are both in the same field, both freelancing, and both have 10-year-olds, you’ll still make different choices, lead your families in different ways, and feel differently about your work. On the flip side, everyone who is what I call a “workparent” entrepreneur faces some important commonalities. Raising kids while working outside of a standard employer or paycheck job inherently comes with certain realities, pressures, and, yes, upsides. Whether you’re an entrepreneur thinking about expanding your family or a parent mulling over going out on your own, it’s a smart idea to know precisely what you’re getting into. Why drive with a blindfold on when you could have a nice clear view of the road up ahead?

I’m going to give you some important truths about entrepreneurial parenting straight from the source. These truths come from a diverse group of moms and dads who are there and will tell us what they wish they had known earlier on. After hearing their best, unvarnished advice, you’ll have the chance to ask yourself some challenging questions — ones that will help you improve your entrepreneurial plans and confidence.

Truth No. 1: Entrepreneurship and Parenting Can Mirror Each Other

And they can do so practically and emotionally. Both are all-consuming, particularly at the start.

Truth No. 2: There Is Never a Perfect Time to Become an Entrepreneurial Parent

You’ll have to decide if and when to make the move — without praise or permission. There is no ideal or correct time to expand your family, take on more at work, or change jobs. The same holds true here. If you’re looking for the Golden Window of Opportunity to become a working-parent entrepreneur, you’re going to be looking for a long time. Carefully weigh the pros and cons, and then make your own call. Be confident in your choice because you don’t need, and probably won’t get, a lot of encouragement.

Truth No. 3: Your Business Model Matters

It’s not just about having that marketable skill or great idea. You need a revenue plan — one that takes parenting into account. As basic as it sounds: Know how you’ll make money. Don’t assume that because you’re self-employed, your situation will be working parent-friendly. Be honest with yourself about how much time you want with the kids and carefully manage your income stream and cost structures to allow that time.

Truth No. 4: Systems and Infrastructure Are Essential

Without them, you’ll spend a lot more time away from the kids. Being your own boss can bring tremendous freedom, flexibility, and focus on big-picture issues. It also brings responsibility for handling all the underlying operations: IT, tax reporting — all the infrastructure you may have taken for granted when working for someone else or inside a larger organization. Unless you’re realistic, creative, and disciplined about those demands, they can become overwhelming.

Truth No. 5: Watch the Pennies

As a working-parent entrepreneur, you’ll want to redouble your attention on costs and spending. When you work for a bigger organization, the budget may be tight, but it’s the company’s money, not yours. When you work for yourself, that distinction usually melts away: Your personal and work finances can become inextricably linked. That means taking an extra thoughtful approach to spending money and saving it.

Truth No. 6: Grow at the Right Pace

Be deliberate and decisive as to what that means. The whole “they started a company and sold it two years later for zillions” story is compelling. Who doesn’t want that kind of quick success (and cash)? As a parent, though, you may find rapid growth working against you, leading to excess time away from home and to burnout. Set your growth intentions and stick to them.

Truth No. 7: Family-Friendly Benefits Aren’t Exclusive to Big Corporations

You may be able to (re)create some of them on your own. That corporate backup care plan, the lactation room, the working-parents network — they’re all great perks. But those perks don’t have to be career-deciding if you can find or build similar supports at an entrepreneurial company or by working for yourself.

Truth No. 8: You’ll Need a Village to Help Raise This Child, Too

Be realistic about the support you need and creative in how you get it. The more help you can get, the better. Think outside the box but systematically about who can lend a hand.

Truth No. 9: Flexibility May Take on a New Meaning, Require an All-New Approach, or Prove Elusive

In fact, you may have to work even more. Entrepreneurship is not — I repeat, not — the Land of Milk and Honey when it comes to time- and stress-management. When you’re the boss, you’re accountable. When you’re accountable, you typically have to put in a lot of sweat equity. Yes, there may be upsides, but think through the specifics of how an entrepreneurial career would affect you and your family situation.

Truth No. 10: Good news: You Get to Set the Boundaries. Bad News: That May Be Very Hard to Do

When you’re working for someone else, the on and off switches are more clearly marked. Now they may be hazier, dynamic, or harder to find. You’ll have to your boundaries without guidance, precedent, or anyone else’s express approval.

Truth No. 11: Taking Time Off May Be Tough

Or it might carry some very real consequences. It’s hard to be off when you’re the one bottom-line accountable, and there’s no paid leave, but you can try taking different kinds of breaks than the ones you’re used to.

Truth No. 12: Working for Yourself Gives You the Power to Create a New and Better Working-Parent Template

This is helpful to you and other working parents. In forging your own path, you get to be part of the solution.

Alright, so your eyes are now open to the always-there, unavoidable realities of entrepreneurial parents, both good and bad. Any vague thoughts or idealizations have been replaced with a more specific, grounded view. Perhaps some of your worries and fears have been soothed a little as well. But now you’re facing a new question: How do the realities we’ve covered apply to your life, career ambitions, skills, preferences, and family?

Whether you’ve just begun toying with the idea of becoming an entrepreneur-parent or have been at it for years, these questions will help you reflect on how to make this professional pathway best come together for you. Pretend you’re discussing your answers with a supportive friend or mentor — someone who won’t snap at you, laugh, or judge, but who won’t take your first glib response as a final one, either. Imagine that person nudging you a bit, challenging you to be as truthful and unguarded as possible.

If you want to have this conversation with an actual, real-life partner, you can. You can also use the imaginary mentor technique as a safe, effective means of iteratively thinking things through on your own. Either way, the goal is to gain greater clarity into what working independently and entrepreneurially means within the context of your own life — and what actions you may want to take as a result.

As you work through each question and pressure-test each of your own responses, you may come to some specific, personal insights: that you’ll need to change how you handle your business’s IT needs, for example, or that you don’t want to go freelance until after the twins are in school. You may also have the feeling that you’re swirling, that you don’t have perfect answers to any of these questions. However disconcerting, that’s just fine.

Remember: An entrepreneur is simply someone who organizes and directs a business, taking on the responsibility and risks of doing so. As an entrepreneurial parent, you don’t have to be able to see the future or have perfect answers to every possible question. Your whole life need not be neatly tied up and topped with a bow. You simply have to be willing to organize and direct your career and family life and take on responsibility for doing so. In thinking through the challenge questions, that’s precisely what you’ve just done.

Now, whether you’re already working long hours at a startup, are just thinking about hanging your own shingle, or have decided not to go the entrepreneurial route after all, there are powerful ways to bring together your unique career and your life with the people at home.

Reprinted by permission of Harvard Business Review Press. Excerpted from Workparent: The Complete Guide to Succeeding on the Job, Staying True to Yourself, and Raising Happy Kids by Daisy Dowling. Copyright 2021 Daisy Dowling. All rights reserved.

Versions of this article originally appeared on SUCCESS.com and in the July/August 2021 issue of SUCCESS magazine.

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