Advice I'd Give My Younger Self Before Leaving Corporate

Advice I'd Give My Younger Self Before Leaving Corporate

I’ve had a lot of conversations lately with people curious about my own experience leaving corporate:

  • "What are the ‘right’ steps?"

  • "How do I know when to leave?"

  • "Is it better for me to dip my toe in or should I jump in head-first?"

All good questions.

Leaving your corporate gig to become a business owner, freelancer, or student—or even taking a breather to figure out next steps—can be intimidating at best and paralyzing at worst. If you’re one of the committed few, I congratulate you. It takes courage, conviction, and grit to take the leap…and even more once you've leapt.

I've spent 20 years helping people get more comfortable with change. The biggest takeaway? It's really freakin' hard. 

I'd also tell my younger self to read the warning on the back of this plate I used as a child and through most of my adulthood much sooner.

I'd also tell my younger self to read the warning on the back of this plate I used as a child and through most of my adulthood much sooner.

That said, change is going to happen regardless, so we might as well steer the ship ourselves. 

These conversations forced me to reflect on the biggest lessons learned from my transition from corporate lackey to business owner/coach/writer.

Here are 4 pieces of advice I’d give myself if I were making the transition again. 


1.  Keep What Serves You, Discard the Rest

My first rule is that you get to set your own rules.

This applies to this very blog post and anything I say from here on out. If my advice works for you, great. If it doesn’t resonate, you have my permission and blessing to ignore it. 

As I progressed in my career, I found it increasingly maddening that there was set of rules I was expected to follow—whether they made sense or not.

I felt stifled, like each day I had to choose between toeing an arbitrary line and being the leader I wanted to be. I couldn’t do right by my people and carry out the organization’s priorities. 

So when I started my business, I was unpleasantly surprised by how many people told me I had to do xyz to succeed as a business owner. Worse, everyone was presenting their set of rules as the only way.

I wanted a successful business on my own terms, one in which I could be authentically and unapologetically myself. 

My overarching priority in life is to Keep Things Simple. If someone’s advice helps me do that and aligns with what I’m looking to create, I take it. If their advice feels weird or incongruent with my values, I leave it.

YOU GET TO MAKE UP THE RULES. Keep what serves you and discard the rest.

Whether you’re leaving corporate or simply transitioning into a different phase of your career, identifying—and then honoring—your vision and principles first will help you create a career that’s 100% you. All the other steps will fill themselves in.


2.  Mind the Gap

In 2017, I changed everything about my life

Am I grateful for this period of exponential growth? Definitely. 

Was it awesome to go through? Not particularly.


It was a rocky road. While all my friends were shockingly supportive, I leaned the hardest on the ones going through their own transitions because they understood first-hand.

One thing I’d do sooner is proactively seek out people who were slightly ahead of me in making the same sorts of changes. I found myself ricocheting between people who had already crossed the finish line and those who were in the early stages of their transition. I couldn't relate to either. 

It's helpful to have a point on the not-too-distant horizon to pull you forward to something markedly better yet still attainable. 

When people are too far ahead of you, the gap can seem too wide. When they’re in it with you, it can be tough to see the way out. Either way, it’s easy to despair.

The practical steps are the easy part. The hard part is the barriers you’ll put up for yourself.

You’ll need a support system and role models for when your limiting beliefs threaten to get the best of you.


3.  Look Before You Leap, But You Gotta Leap

There is no “right” time to leave.

Everyone has a different game plan and timeline. I refer you back to #1.

Plan, plan, plan. Then plan again. Then plan some more.

But no plan can accommodate every scenario, and eventually you have to put it in motion.

If you like, use your corporate gig as long as you can to bridge the divide. But when it’s no longer helping you achieve your ultimate career goals, move on. 

Get crystal clear on what you want to accomplish there, set a date to achieve it, and honor that date. Three to 9-months is usually a good benchmark--long enough to accomplish something but not so long you get sucked back in. 

The goal here is "yes, and" synergy, where your day job is furthering your longer-term career aspirations (versus an either/or situation where your corporate gig is competing with them.)

There will be so many temptations to talk yourself out of leaving. I know because I succumbed to most of them. I originally went part-time in my corporate job thinking I’d do it for six months, tops. I finally left 2.5 years later. Some of that time was intentionally-focused on furthering my business goals; some of it was fearful clinging.

As my last gasp, I created a proposal for a women’s leadership program, thinking I could effect real change for high-potential mid-level women and insinuate myself into the program as a coach. I enlisted a senior sponsor, and we shopped it around. No takers. At that point, I knew there was nothing left for me there. Every day I worked for someone else would be time spent away from working on the career I really wanted.

Create your plan, set your date, then get the heck out of dodge. 


4.  Baby Steps To Happiness

Patience is not one of my strong suits. 

Never in my career have I had to practice more patience than as a business owner. 

When I was in corporate, people used to say, “It’s a marathon not a sprint.” I was like, “See you later, suckers!” as I scrapped and pushed and clambered up the ladder.

That approach is exhausting, and it simply doesn’t work when you’re building something from the ground up. It takes time and patience.

When you're first starting out, you start to see all the possibilities, and it's tempting to try to do everything at once. This can lead you to take on too much or discourage you because you're not moving fast enough.

Especially when you want results NOW.

Instead of 6 months or a year ahead, think 2, 5, or 10 years. Then design the baby steps to move slowly forward. Soon your goals are impossible NOT to achieve and often don't take as long as you thought.


Remember the Upside

There’s so much fear around leaving corporate, yet I know no one who’s left that wants to go back. Ever. That says something about what awaits you on the other side of that fear.

If you don’t like what you’re doing, there’s no reason to tolerate it for longer than it takes to develop a plan to change it. 

My career and life transitions have been hands-down the best moves I’ve made. They’ve not always turned out as expected but always got me to a better place. And I wouldn’t trade for anything the feeling of having tried.

Whether you've committed to leaving or are still on the fence, I wish you strength and intentionality in deciding the right move for you. I'm here if you need help.


If you want to hear more about my twisty-turny career journey, here's my story.

If you’re looking for concrete steps and a path forward, grab my free 4-step roadmap.

If you're contemplating leaving your corporate job, what's holding you back? If you've already left, what's your biggest lesson learned?

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Author Bio: 

Before becoming a coach, Caroline spent 20 years in management consulting and financial services. She's made it her mission to help people grow, contribute, and get wherever they want to go.

Caroline wants women to recognize how much power they truly have to define their careers. The life and career you want really is possible once you have the roadmap. Take the first step by downloading her free guide.

She’s also a tennis fanatic, aspiring Minimalist, FIRE (Financial Independence and Retire Early) enthusiast, and Aloha Spirit seeker 🤙. She loves to share stories from her unconventional life and career focused on freedom, creativity, fun, health, family, and community. If she can do it, you can, too.