Quit Without Regret: Surprising Secrets of the Scenic Route

You say you want to quit your job, but are you?sure?

Six years ago, I was running a billion-dollar media account with three children under three years old, and life was moving way too fast.

I was the primary breadwinner, my husband was a stay-at-home dad, and I thought we made our choices and had to live with them. But when I saw an opportunity to raise my hand for a package, I ended up in unfamiliar territory.?

Since then, I have learned surprising lessons about life and business, found unexpected treasures, and never looked back.

If you dream of leaving corporate life behind but wish you could see into the future first, this is what it looks like after the excitement wears off.?

ONE

I’m as ambitious as ever, but it feels good to have a broader definition of success.

The things I love — quality time with my family and friends, travel, cooking, homemaking, gardening, wine, good books, walking my dog, and being outdoors — are all a part of my day-to-day life. I think of this as diversification.

Despite society’s emphasis on salary, income, and multiple revenue streams, most of us dream of measuring our lives beyond finances. My new definition of success includes happiness, well-being, fulfillment, travel, family time, passion projects, and business.

When I stopped comparing myself to others or where I would have been if I had stayed the course, I felt free to love the journey I was on.

It turns out that when you love your days, it’s pretty easy to love your life. Give yourself permission to evaluate life on your terms.

TWO

I’m getting paid to study the topics I find endlessly fascinating (and truth be told, I’d do it anyway).

I started a folder in high school with a collection of quotes, ideas, and people I was genuinely interested in, and it grew throughout college and early in my career.

I didn’t necessarily know why I had it, but it was a growing source of inspiration, kind of like Pinterest before Pinterest.

All these years later, I still deeply invest in subjects I love. Not all of my work is directly related to that folder, but there is overlap.

My inspiration board has come to life, and I get to incorporate what I love into growing my business and raising a family. I’m a writer. I’m a coach, a mom of three, a wife, a dog mom, and a homeowner. I love my many roles, and I like being able to give my full attention to what I love.

THREE

Flexibility matters, especially for women.

Without getting too far off-topic, men have 24-hour cycles and women have 28-day cycles, and energy, attention, focus, confidence, and moods fluctuate accordingly.

That works great for men in a 9-to-5 job because men reset daily, but not so great for women who have weekly shifts that affect productivity, creativity, and collaboration.?

Add pregnancy or kids to the mix and multiply by a billion (give or take).

But the thing about working for yourself is you can manage your work to suit your cycles. You can take advantage of your natural preferences and harness your energy. I stay in the zone when I’m feeling fierce, opt out when I’m not, and optimize my schedule for my life.

Time, location, and creative freedom are huge advantages that show up in little ways first — extending breakfast with the kiddos before school without pressure to be early to the office or writing, editing, and publishing on the same day because there’s no red tape.

If, while working remotely, you had a taste of flexibility, imagine what it will feel like to WFH without one eye on your boss’s agenda. When you are doing your own thing, you can step away from your office, laptop, or even your phone and be untethered for as long as you like.?

As your freedoms compound, you forget how it feels to be beholden to anyone but yourself. I don’t want to overstate it, but it could be considered anti-aging.

FOUR

It turns out that I value my time above almost everything else.

Sometimes I still waste time scrolling social media, binging Bridgerton, or cleaning out a closet because I’m a real person. But now, I think of time differently and don’t focus so much on the tradeoff.

Instead, I prioritize what matters, strategize what’s working, schedule what moves the ball forward, celebrate my wins, charge for my expertise, and don’t sweat the rest.

I’m 100% committed to my business, but it gets done when it gets done, or it wasn’t that important. If it matters, I find a way to make it happen even faster.?

If it fits in my life now or leads to something my future self will appreciate, I’m in. I try not to dwell on a to-do list that pulls me off purpose or detracts from happiness because I’m modeling that for our kids, and how I prioritize speaks volumes.

FIVE

I’ve learned I can trust myself to keep leveling up without carrots or sticks.

When I thought about leaving, I was scared about not having a big brand to lean on. I assumed doors would slam in my face or people wouldn’t take me seriously. I thought that I’d never make it to the top if I had to build my own momentum.

It turns out I’m more creative, innovative, disciplined, and driven than I knew. Now that I have ownership of that, if there’s something I want to achieve or create in my business, it’s magnetizing.?

The pull of creating results keeps me focused, anticipating what’s next, and in a growth mindset. That’s light years away from “just do it because I told you to” or working to earn a short-term bump or promotion.

SIX

The upside is all mine {insert evil laugh here}.

In my corporate life, when I first started managing a billion-dollar account, I barely cracked six figures. That disconnect was notable, demoralizing even. Worse still, if I crushed it or didn’t, the equation stayed pretty much the same.

Now my salary reflects my work. The better I get at coaching, the more I charge. The better I get at marketing, the more leads I have. The better I get at sales, the more conversions I make. The better I get at writing, the more effectively I attract an audience. It all flows together and compounds in my favor.

Of course, there’s pressure in that, but the diamond-making kind.

SEVEN

Learning and growth are directly tied to my bottom line too.

I was lucky to have maxed out my corporate budget on professional growth via conferences, workshops, and continuing education. Still, the difference is that now, there’s always a direct tie to the benefit of my business.

I’ve talked before about how one of the disadvantages of climbing the corporate ladder is that the better you get at what you do, the narrower your focus. While in the short term, that develops expertise and mastery, it can be stifling over time. You lose perspective when you’re not plugged into the bigger vision.

As an entrepreneur, you are iterating towards your own big vision, which means that your business grows as you grow. It’s all under your purview. If you aren’t growing professionally and personally, you will burn out before seeing it through.

That’s the difference between growing a purpose-driven business vs. the hustle hard, scale fast model. You can’t grow your business at the expense of your family and have it work out in the long run.

If you’ve heard the phrase, success loves speed, let me offer a more balanced approach: Success loves sustainability too.

EIGHT

Meetings are thankfully a part of my past.

If you’ve ever read the Four-Hour Workweek or studied organizational productivity, you know that meetings are the bane of business. Yet, companies like Amazon have rigorously outlined how to improve, minimize, and optimize them because they’re often necessary.

But as the boss, you can quit them too.

I found that no matter what I call them now: conversations, coffee chats, coaching, strategy sessions, enrollment calls, conversion events — it’s not the designation that matters — it’s the outcome. If the meeting has a specific purpose with time constraints, it’s not a quote-unquote meeting; it’s a scheduled outcome. I’m producing results via collaboration.

Meetings — Meeting to meet, rehash, develop advocacy, presell, smooth ruffled feathers, manage up, manage down, touch base, see what comes up, and get to know each other — are soul-sucking. It’s a waste of time, and you know how I feel about time.

NINE

Regret has no place here.

I’ll spare you the pithy YOLO quotes even though I secretly love them, but I live by the idea that nothing is as precious as time, and what you do with it says everything. As such, my family is front and center of every moment and decision of my life.

Do I miss some of the unplanned moments of corporate life? Yes! Bumping into someone in the hall, having deep conversations over cocktails after a late work session, or traveling with colleagues and clients meant for some great bonding and lots of fun, but none of it compares to unfettered quality time with my favorite people.

That might make me selfish or one-dimensional, but that’s where I’m at. Utterly content. It’s a season — one that’s fleeting, so I’m doing everything I can to make the most of it.

I don’t regret one minute of the last six years, and there’s absolutely no way I could have said that if I was still in corporate. That’s the litmus test for me, and it’s pretty clear.

TEN

Revenue can be a rollercoaster, but it’s just business.

I’m finally systematizing my business to create revenue predictability, and honestly, I don’t even care that it’s taken three years to get here. Ok, I do care. Would it have been great to replace my corporate salary in less than a year? Absolutely, but as I said above, regret has no place here.

The thrill of the hunt, watching yourself create demand for something you invented, seeing the cumulative effect of following your instincts, and watching your clients fall in love with your work is the best.?

I suspect you are wildly underestimating how good it will feel to create your future, especially given the uncertainty of corporate life. Job security, as you know, is a thing of the past.?

However, if you are contemplating leaving corporate life behind, make sure it’s a goal you can live with because it will take time to find your way. Ask yourself how your business fits into your life now and six years down the road — do you get excited or sick to your stomach? Do you have the stamina to hang in? If you don’t, you’re back to the hustle equation, and you might as well stay in corporate. At least there, others can share the load.

There are months that I miss my revenue targets by a mile, and I would have thought I couldn’t handle it. It turns out, I shrug and move on because I know the months that I get an in-app pop-up that says, Did you know you beat last quarter’s revenue by 451%, are coming. When they do, I smile and move on.?

It’s a bit of a rollercoaster, but there’s no way to get through it other than to experiment. And who doesn’t love rollercoasters?

ELEVEN

I get to bring my whole self to work.

This might be more relatable to minorities, but corporate life can mean holding back. There’s always a part of you that doesn’t quite fit, a skill that isn’t called for, or a role in which you have to downplay your identity or strengths. It’s a systemic issue.

So, it is gratifying to show up fully, authentically, and do it my way while unabashedly loving it. When clients get me and want to work with me, it’s very validating. Ok, understatement, it’s f*&king amazing.

TWELVE

The rewards of corporate life are still accessible as an entrepreneur — it’s just different.

Leaving corporate life behind is exhilarating, but it’s a time of unsettled anxiety too. And the more you make in corporate, or the more your family relies on your benefits, the harder it will be to leave. It’s not riskier per se; it’s just that your corporate life is more fused with your identity. But after you untangle who you are outside of your title, the things you worry about losing are usually about money.?

Your 401k, benefits, paying off your house, and saving for college or retirement aren’t not necessarily off the table. If you’re financially motivated, you’ll figure out how to be profitable, so don’t let that be the thing you holding you back.?

Instead, focus on the long-term upside and non-financial benefits. Building a business is a journey of self-discovery, and if you aren’t fully utilizing it to that end, you’re missing out.

What would you trade for money?

I didn’t know what was next. It wasn’t like I had a dream to be an entrepreneur. I just wanted to write more, mom more, and figure out how to replace my six-figure corporate salary to be home with my kids.

A good gut check is to follow your corporate path forward, then follow your entrepreneurial path forward. Which one leads to where you want to end up and feels more rewarding during the climb?

That’s really telling. After I left, I was so happy at home that everything else was just a detail to be worked out. The pay-off was instantaneous and lasting. How often can you say that??

After a while, it didn’t feel crazy anymore; it just felt like my best life.

What will you find in your life after corporate?

My corporate career was a great place to develop my skills and preferences.?But ultimately, for me, there’s something richer and more rewarding about having the benefit of both experiences.

When I left in 2016, after twenty years in corporate, I yearned for a total reset, so we took a two-year sabbatical as a family. What followed was an epic trip to the other side of the world, a book, a blog, and the inevitable launch of my business. Oh, and a pandemic.

I needed that time to drop my baggage, leave my bad habits and limiting beliefs behind, and reclaim my life. You may not need that.

I was opening up to new possibilities wildly different from the ladder I was white-knuckling. You may already know what you want to do next.?

I didn’t have a brilliant idea, but I was willing to bet on myself, and my vision of being home with my babies mattered more than my fear. That was six years ago, and the time with my family has been priceless.

What matters to you more than your fear?

If you dream of something more for your life but are afraid it will take too long, be too far to go, or have to risk too much to find it, you aren’t alone.

No one but you gets to decide when to quit, how fast to go, or what you are willing to give up to make it happen. It’s your decision from start to finish, and worst-case scenario, you can always go back. But if you can’t let go of the idea, the pain of postponing the life you want doesn’t usually go away.

For a while, I was motivated to get to the top as fast as possible, but then, I wanted something different. Now the scenic route holds a special appeal.