WOULD YOU STILL DO IT?

The real cost of starting over—and what happens when you take the leap.

There’s a strange difference, a distance almost, between wanting to do something and actually doing it. Especially when it comes to business or identity. You can read a hundred books about self-growth, entrepreneurship, founders’ stories or starting over to quiet the monsters of self-doubt, fear and rationale, and still, there’s no guarantee when these debates begin that you’re actually going to do it.

I’ll tell you why.

As life rolls along, you become someone. Every year advances and you become an advanced, or sometimes regressed, form of the person you were previously. The point is, you’re changed because life constantly changes. You either advance, stagnate or fall back, but you’re changed. And all the stuff, good and bad, that comes with life comes along with you.

So the question becomes: Can you let the good come along with you while releasing what doesn’t serve you, including some of the comfort you’ve grown accustomed to, in order to become a future someone, or something, you don’t yet know?

Most people probably say no. And they wouldn’t be wrong.

Reinvention comes with a price tag. Risk. Growing pains. Uncertainty. Sometimes loneliness. The road of doing something only you can do is, in many ways, a solo trip.

But back to those pesky deliberations. This is where the rubber of you hits the road. Where your conscious and subconscious merge. Will you do it? Or will you not?

In the middle lies your personal go/no-go zone. Sometimes go means answering a higher calling, which often includes taking a more difficult path. Other times, not going somewhere is as important as going. This, too, can be an honest reality check about life: what you really want, what brings you true contentment, or what you have the realistic bandwidth or desire to do with it. Both are honest questions with equally honest, and admirable, answers.

Knowing yourself well enough to optimize your life for whatever that answer is? That’s purpose too.

In my case, two things played on repeat. One, which I’ve mentioned a few times before, was just the little girl in me always believing and thinking I was going to grow up to be something larger than myself. That I carried a sense of purpose and responsibility. The bracelet I wore, and still have, that says, Remember who you wanted to be.

And, more silly but true, nothing like a great ad campaign! That Nike ad just kept bouncing through my mind.

Just do it.

And even then, given the distance we somehow place between ourselves and this thing, you look back and barely remember jumping. It’s almost as if that very conscious choice wasn’t conscious at all. Like it was hot to the touch and you needed to let go of it as quickly as possible. As if it wasn’t your responsibility at all.

And yet, it was.

That’s the way it felt to me, at least.

And here I am.

THE ROAD LESS TRAVELLED

There’s No Waze for This

In retrospect, I probably bit off more than I could chew. I didn’t know it at the time, but the path I had chosen for myself would be filled with far more work, worry and complication than I expected.

And I expected a lot. I had spent a lifetime, really, contemplating and searching for the right time and opportunity to do just this. I had prepared myself and my plans, and had done all the competitive analysis for months. And I had lived through storms aplenty. I was ready for rough waters.

Plus, I had spent years acquiring skills and experience across different careers that, together, constituted almost everything I wanted to do. I had been a journalist, television anchor, news producer, luxury retailer and product designer. I had become an experienced home cook and interior designer.

Now, I wanted to combine everything I’d learned to create a platform offering a deeper, more taste- and individuality-centered framework for building a beautiful life. One rooted in developing a taste and point of view entirely your own.

Don’t get me wrong. I know we live in a highly saturated world with a gazillion options for choosing pretty things. Commerce is tricky. Social media? Maybe trickier. But so much of it is flat. Or fake. Real beauty requires going beneath the surface. I felt depth was sorely missing. And I was determined to change that.

Design had taught me something important too: how to put things together. How to take disparate pieces and assemble a whole that made things more beautiful. How to create a plan, a blueprint, structures to bring precision and efficiency to life.

Another truth: I had always wanted to do more than just design. My projects were giant lifts; a single job could last a few years. I loved the process, but it often felt like climbing a mountain, only to reach the top, come back down and start all over again. I wanted to build something more lasting.

The timing was right too. AI and technology were changing everything, eliminating much of the guesswork and even field time. I could, in essence, build my own laboratory and generate more ideas, more design and far more information than I ever could one-to-one, while still taking on select projects. It felt like something broader and more sustainable, creatively and financially.

So here’s the first thing I’d tell anyone choosing a new or less travelled road: bring everything you’ve got. All of your life’s experience and work. You’ll need every bit of it. Bring a healthy appetite for learning and organization too, because every resource and skill you have will count.

There’s no Waze for uncharted waters. You simply can’t anticipate everything that’s going to come your way until you’re in deep.

Entrepreneurship can be incredibly rewarding, but prepare for a long swim that includes treading a lot of choppy water and, oftentimes, swimming upstream.

LESSONS IN LEARNING

Boots On The Ground

If starting over for you involves a new business, here’s the funny thing: you can go to bed one night and wake up the next a newly minted entrepreneur or founder. The title comes fast. Almost nothing else does.

Except learning. You’ll need to do that as fast as you possibly can. The faster you learn, the faster you move from square one to square two, then three, and so on.

And that’s with bringing all your experience, education and wisdom from the past.

I always try to remember that most things worth having are rarely easy. They can be simple, but they’re rarely easy. The intrinsic value of most good things is care, and with care comes time and effort.

Here are the biggest lessons I’ve learned so far. Some are probably universal. Others may be unique to me. Either way, I hope they’re helpful. I didn’t learn all of them fast. In fact, contrary to thinking I was a fast learner, there were times I felt really slow this past year.

Sort out your head first

There will be plenty of battles with yourself over the course of building something new. Whether you should or shouldn’t have done this thing doesn’t need to be one of them. You did it. It’s go time.

Be on your side.

Decide to be your own best friend, advocate, mentor and advisor. You’ve really got to be aligned with yourself because, there are plenty of days when there’s no one to call but you. So be good to that person. Trust that person.

Whatever amount of money you’ve dedicated to this venture, double it.

Whatever time you’ve dedicated to it, triple it.

Preparation is just the pre-game.Whatever you did in the lead-up—learning, competitive analysis, due diligence, planning—it doesn’t scratch the surface of the learning, analysis and continued diligence it will take just to get your bearings. And that’s just the first year.

Get ready to work. A lot.

Your nine-to-five can quickly become nine-to-midnight and beyond. Seven days a week. As a founder, you work even when you’re not working. Create a schedule and try to stick to it. Routine provides structure when nobody else is there to provide it for you.

Learn how to learn again.These are two kinds of learning. One is natural; it’s continued learning as you progress through life. The other is fundamental learning. This is ground zero learning, required when you change a skill set, for instance when you change careers or expand your expertise into something entirely new.

Here’s why it can feel so difficult. With experience and repetition, the brain develops what researchers call automaticity: things that once required considerable conscious thought become faster and require less mental effort. When you become a beginner again you lose some of that advantage. New tasks demand more attention, more conscious processing and, naturally, more time.

In other words, one of the hidden costs of reinvention is giving up the speed of expertise.

Strap yourself in. Some of it will feel foreign and, at times, brutal. I’ve been humbled more times than I can count this year.

Get comfortable with the ick.

At some point, you will exponentially increase your cringe factor. Whether you’re in the public eye or not, you’ll have to do things that make you uncomfortable, make you feel like an imposter or even embarrass you as you begin showing up as something different from what you’ve been in the past.

Build good ear muscles to hear no.

Or for something not to work. Or to be rejected. It comes more often than you expect, and somehow the more you want something, the harder and faster the no’s seem to come. Just try to remember that some of the greatest success stories included years of no’s before the yes ever came.

Accept that you will do things over.

You’ll do something only to discover, for any number of reasons, that you have to do it all over again. Then again. And sometimes again.

Steel yourself against what other people think.

This includes family and friends. Most people won’t understand why you would risk comfort, expertise or financial security to do something different with absolutely no guarantee. They don’t necessarily need to understand it. You do.

Some relationships will change.

Sometimes simply because you’ve declined dinner for the fifth time because you’re working late or through the weekend. Other times because you’re becoming a different person, and change can alter relationships in ways you never anticipated.

Be prepared to be alone. Even lonely.

Doing something only you can fully do or see can leave you physically and philosophically alone. That doesn’t necessarily mean you’re on the wrong road. But it’s worth knowing that it can be as lonely at the bottom as it is at the top.

You are the asset. Protect it.

Investing in a new business is an investment in you. Whether you exercise, meditate, walk or have some other practice that keeps you balanced, make sure you have something that builds physical, mental and emotional strength. Your body and mind are going to be stretched.

Your energy is capped.

Just like the hours in a day, you have a finite amount of energy and reserve every 24 hours. If you’re not minding how you expend it, along with your time, and how you recharge your battery, eventually you’re going to go dead. I kid you not.

Making money will take longer than you think.

Unless you’re extremely lucky, turning a new idea into an actual business is likely to take considerably longer than your original plan suggested. Hand raise here.

Overnight success takes ten years.

There’s a running joke in entrepreneurship that it takes ten years to become an overnight success. There’s more than a little truth in it.

Some get lucky, yes. But, we rarely see the years it takes most people to achieve success: the unanswered emails, the hundred nos, the ideas that went nowhere, the pivots, and days when absolutely nothing worked.

IS THE PRICE RIGHT?

Quid Pro Quo

Here’s the real quid pro quo of starting something new: You want something from it. And apparently, it wants something from you.

Time. Money. Energy. Comfort. Certainty. Sometimes your social life. Starting something new has a way of reaching into parts of your life you never included in the original business plan.

For me, one of the biggest surprises was how isolating it could be. I’ve been alone a lot. And I suppose some of that was necessary. My best friend called recently and asked what I was doing. I told her I was talking to Whispr, Claude and Chat about something I was trying to figure out.

“My bestie has no one to talk to, so she’s talking to AI again,” she said.

She was joking, and it was pretty funny. But she wasn’t entirely wrong. I had to laugh. I was a little sad for me!

Here’s the truth: I often don’t commit to plans because there’s never enough time in a day to finish all. Work runs into evenings and weekends. I decline dinners because I frequently need to stay in the office late, and I protect my weekends because they offer the one luxury I don’t have during the week: uninterrupted time. To work more. The work has definitely put a dent in my social life. As hard as I try to strike a balance, more truth: I’m not doing a great job of it.

Maybe this is necessary for now. I keep telling myself anything worth having costs something. I’m betting the house on all this, so naturally it comes with a pretty big price tag.

But one year in, as much as I love work, I’m increasingly aware that this pace isn’t sustainable long term. The objective can’t simply be to build the new thing. I have to figure out how to build it while maintaining some balance. Otherwise, what am I building it for?

Quid pro quo.

THE BET’S STILL ON

One Year In

Has it been worth it all so far? Absolutely.

This year has been one of the most exhilarating of my life. On a good day, I swear I feel like I’m 30 again, returning to parts of myself I haven’t felt in years and discovering so much that’s new while pushing against a very steep learning curve.

It’s a strange combination: feeling so inspired, youthful again, but with a lot more experience. I only wish I could push back the clock to gain more time. But the right time comes when the timing is right.

The only way I can describe all this: it’s akin to living in a whole new world while imagining a very different one ahead of me. I should probably give some credit where credit is due: the median age in my office is 25. That helps :)

All of this to say, I’m happy to be here. Happy that I’ve made it a year. Maybe because starting this new thing has made possibility feel wide open again.

But I’d be lying if I didn’t say there have been equally difficult days. Days when, despite my own excitement and belief, the world hasn’t mirrored either back to me. Days that have caused fear and doubt, not necessarily about myself, but about fate, chance and timing, and whether all of this will ultimately become what I believe it can.

I’m not writing this from the other side of a success story. I’m only a year in. It’s just the beginning. A report from the field. I haven’t arrived anywhere.

I’m still betting. Betting on my vision. My plan. Myself. Just drawing up new maps and directions as I go, and as I learn.

Some continue to say I’m risking too much. They may be right. I’m betting they’re not. I’m certainly praying they’re not.

That’s because there have been years, months and days that have felt like Groundhog Day. Do you know that feeling? When you wonder if where you are is simply life’s lot, if this is as good as it’s going to get, despite your efforts to change it. Starting again has opened up possibility. And that’s a beautiful thing.

I don’t know exactly where this road leads yet. But I know I’m glad I took it.

Would I still do it?

I guess you’ll have to ask me again next year.

THE GO/NO-GO ZONE

Know Yours

So back to that go/no-go zone. Maybe you’re not starting a company. Maybe you’re considering a career change, a move, a project, a relationship, or simply something you’ve wanted to do for so long that wanting it has become almost as familiar as doing nothing about it.

I can’t tell you to jump. No one can. But I can tell you that if you decide to embark on something sizable or new, even risky, you’re never going to feel completely prepared. You won’t know exactly what it will cost, what it will ask of you, or who you’ll become in the process. That’s the risk. It’s also the possibility.

The real question is whether the life on the other side of that decision is one you’re curious enough to go find out about.

And if it is, maybe you don’t need to see the whole road ahead. Maybe you just need to know yourself well enough to recognize when it’s yours.

Then go.