Executive to Entrepreneur: 4 Key Lessons
Plus, a Real-Life Example of a Simple Framework for Keeping Your Priorities Front and Center as You Transition
Maybe you’ve been contemplating the transition from executive to entrepreneur for some time, but there was always something holding you back — family responsibilities, pay/benes, fear, uncertainty, complacency, timing, something. Now that you’re ready or you’ve recently embarked, you’re looking for key lessons to help you contemplate or navigate your own leap.
There’s probably a sweet spot, somewhere perhaps in your late 20s/early 30s when you are young, fearless, optimistic, and ambitious, but also have acquired enough skills, life experience, wisdom, and savings to improve your odds.
My tipping point was in late 2016 and I wasn’t really in the sweet spot. I had overstayed my corporate role by a couple of years partly because I was so focused on my personal life that I quit giving my corporate role it’s due. My job didn’t fulfill me, but it also didn’t get in the way if that makes sense, and it did provide a decent paycheck.
By the time I felt compelled to make a change, I wasn’t sure what to pivot to. I knew I wanted to explore something entrepreneurial, but I didn’t know what it was, or what it would take. As I researched, read, and interviewed other entrepreneurs, I instituted a simple framework that clarified my priorities, so I could stay on track during the discovery process. Whatever I explored or however I spend my time, I kept the following considerations in mind:
1) Serve my family first
2) Focus on wellbeing
3) Immerse myself in the digital world, update skills accordingly
4) Write and read obsessively
5) Make a difference
6) Choose something with long-term potential
7) Conduct honest self-assessment
8) Let go of the next thing being “better”, a natural progression, or somehow fitting with what I’d done previously
9) Pursue my passions and stretch my capabilities
10) Be open to signs, synchronicities, and/or inspiration in all forms
It took me longer than I thought to figure out my next move. The day-to-day of the transition fluctuated from big and scary to small and mundane, from “I got this!” to “what the f**k am I doing?”.
During the last two years, I’ve observed four lessons that emerged in my own transition and seem to be consistent with other’s transitions too:
1. Without access to vast resources, you must adapt to create your own resources.
Depending on your corporate experience, you may be used to entire departments filled with employees to call on, from making travel reservations to handling financial responsibilities, from managing hiring, firing, and recruiting to setting company goals, from answering phones to developing corporate, social, and media relations strategies, and more. You may have even been part of creating such vast resources, but they existed before you and will continue long after you leave.
That kind of system is huge — it can activate potential, free up employees to focus exclusively on their jobs, and empower them to accomplish big goals. It takes the pressure off knowing everything, spreads the responsibility throughout the organization, and minimizes risk.
On the other hand, it can also limit decisiveness, prevent meaningful change, and keep employees in the dark about anything outside of their lane. It creates redundancy, bureaucracy, sluggishness, hinders innovation, and promotes consensus thinking. Vast resources require enormous budgets, small cities to maintain, and can evolve into something hard for anyone to get their arms around.
In the entrepreneurial world, you don’t have to worry about vast resources taking on a life of their own because resources are limited. You are a department of one and you must rely on your own intellect, self-direction, and resiliency to determine success.
Figuring it out on your own requires applying the knowledge you have acquired over the years in new ways, adding new skills as you encounter new challenges and opportunities, and learning as you go, all of which makes you more effective, marketable, capable, and confident.
Having to do it all yourself also means connecting the dots in new unexpected ways by having visibility to all aspects of the business, customer lifecycle, promotional mix, behind the scenes operations, and more. You may seek other’s input, but ultimately your decisions are your own and you can move as fast and be as agile as your intelligence and schedule allow.
Not having access to vast resources brings out your creativity and demands that you prioritize, establishing which goals, skills, projects, etc., are worth the time and effort they will take to achieve, as well as worth the opportunity cost of pulling your attention away from other important responsibilities and assignments.
2. Without a boss or team to turn to, you must rely on your own instincts and experience.
In some ways, being an executive means performing a role that embodies a job description or being a collaborator instead of a contributor, whereas being an entrepreneur means bringing an idea to life and seeing where it takes you or being a driver instead of a passenger. Ownership requires some of the skills and experience you’ve gained, but also expertise outside of your comfort zone. It’s a more holistic, less linear, less prescriptive, and more open-ended approach with little oversight. It’s doing something before you’re ready, before you can guarantee a home run, adjusting on the fly, without hierarchy to advise, without a boss teaching you, grooming you, or protecting the company.
In the corporate world, having a great boss is a gold mine. It means invaluable guidance, a direct connection to leadership and mission, and someone equally vested in your trajectory. It can make or break your career. Unfortunately, great bosses are few and far between and leaning on a boss, particularly as a female can be complicated, fraught with political repercussions, inferences, or worse. As a result, many corporate execs narrow their focus to strive for perfection on what’s measured in their performance reviews, which perhaps limits their personal potential or narrows their focus.
In the entrepreneurial world, it’s not about perfection, it’s about production. Mature brands perhaps have the luxury of market share or brand awareness to concern themselves with perfection, to make sure every word, every image, every partnership or initiative is perfect. New brands must hustle to gain awareness and earn customers, to translate vision into dollars. Creating something out of nothing is inevitably messy, spontaneous, and a long game with missteps, mistakes, and efforts that don’t pan out.
When you don’t have a boss to tell you what to do, or a team to share the responsibility, you must dust off the skills that got you hired, promoted, and that you developed throughout your career to create a new combination of expertise, that adapts to the task (and role) at hand.
As mentioned, it’s a different vantage point to be a part of everything. To be immersed in all aspects of a business, soup to nuts, means first-hand insight that demands a level of accountability far beyond following a playbook, adhering to a company manual, or convincing your fellow executives to buy in on your idea.
Executives frequently look for ways to focus on the tasks that are valued by the organization or management and the contributions they are compensated and evaluated on, while entrepreneurs look for ways to focus on moving the business forward and generating revenue. Sometimes they’re the same things, sometimes not.
3. Being in total control of your schedule is an opportunity to maximize your business and personal time.
The desires for freedom and flexibility are often primary drivers of the transition, yet they’re also easily jeopardized. It’s simple to jump in, get excited about something new, and be carried away by the possibilities. But after the honeymoon stage, it’s stressful realizing you are in the deep end with multiple goals, competing priorities, and the pressure of making it work before you run out of money. It can lead to giving up and giving in to the seduction of a corporate role again, bringing someone else in (which defeats the purpose of being your own boss), or working so much that you surrender your lifestyle goals.
Maximizing the benefits of being your own boss means making your schedule work for you and accepting a more realistic timeline. Determining how you can balance progress on your business and still maintain a lifestyle you desire will inform your schedule. If achieving a financially-driven deadline is your number one goal, you probably will have to put in many hours disproportionate to pay in the early days.
If achieving work/life balance motivated your leap in the first place, you may have to prioritize your other roles and accept that the business will grow relative to the time you invest in it. It’s unreasonable to think that you’ll make executive level comp right out of the gate or that you’ll build a spectacularly successful business immediately, or that you’ll be able to play all day and make money.
You may have to find additional motivation, beyond flexibility of working fewer hours or the reward of making more money. Perhaps the freedom of doing what you need to do when you need to do it, both professionally or personally is enough. For many entrepreneurs, being able to lose yourself in the flow (being as productive as you can be when you’re feeling it, when it’s coming effortlessly) of making progress on meaningful work, while still having the flexibility to set it all aside on the days you need to focus on life at home is ideal.
No matter what, setting your own schedule is illuminating because as the sole creator of output, it’s easy to measure how spending your time on different tasks impacts business. After analysis and crucially, the things you may enjoy doing the most might not be the most effective for growing your business. Focusing on revenue-generating activities most of the time is absolutely necessary for viability, but easier said than done.
Keep in mind, there’s no one else to pick up the slack and when everything rides on you, it may mean doing work you aren’t used to doing, don’t like doing, letting go of other more fulfilling work, shoring up skills in certain directions that don’t come easily, or allowing things be “good enough” before moving on to the next thing.
4. When business is personal, it amps up the intensity and motivation.
When you are representing, associated with, or responsible for growing a brand you believe in, it’s empowering — a job or business can be a means of tremendous personal growth. That’s true whether you are an executive or an entrepreneur. The difference is how personal the entrepreneurial journey is. The money, for example, is personal. Managing a corporate budget, no matter the size is stressful and requires diligence and finesse, but it’s not the same thing as spending your own money, knowing your family and your future is impacted by your choices.
When you launch a new business, odds are it’s personal. You’ve chosen a product or service or franchise that matters to you for one reason or another. It represents you, your values, your art, your ideas, or your future. And no matter how rationally you process a missed sale or a canceled customer, if someone opts out, it feels like a personal rejection. When you are so deeply invested, it’s hard to say for sure where you end, and the business begins.
The day-to-day is personal too. Your business must attract your ideal customers or clients. To find them, to appeal to your tribe, you must be ok with turning people off as much as you are with attracting them. That requires confidence, vulnerability, and putting yourself out there. Being an entrepreneur is being completely invested, emotionally, financially, and personally, putting your ambitions on display and letting your vision shape your company’s culture, decisions, and communicating your values to the world.
In contrast, being an executive is more about the climb. There’s a certain emotional distance in that, playing the game, getting to the next level, earning a promotion, expanding your sphere of influence, learning out to act and communicate in a way that is rewarded by an organization’s culture.
And personally, and significantly, you get all the credit and all the blame which is amazing and terrifying. One way to see if you have the stomach for it is to choose a test, pick a subject wildly outside of your core skillset but essential for the business and dive in. Sign up for a small business tax bootcamp for example. Can you do what you have to do, what you’re legally obligated to do, even if you have zero interest in it? Can you focus on aspects of owning that have no appeal for you, knowing there will be consequences for dropping the ball?
If my corporate life taught me anything it was “we”. We as a means of rising together, achieving together, spreading the wealth, spreading the responsibility, minimizing the risk, and avoiding star culture.
The entrepreneurial journey is an exercise in “I”. There’s no one else to pick up the slack, so you must make sure everything in your business continues to run whether it’s work you are comfortable doing or not. I is doubling down on accountability, embracing the full consequences of mistakes, owning the concept, taking responsibility for its development, and being focused on the process, the lessons, the growth, as much as the outcome, knowing if (strong if) it’s a success, you will enjoy the full reward of your efforts, which may wildly exceed what’s possible in the corporate world.
In that sense, it’s embracing rising to the occasion and testing your capabilities, knowing that employees get paid for their role while entrepreneurs get paid for their results.
Good luck!
