How Do I Know if Entrepreneurship is Right for Me?
There is a lot of hype about #entrepreneurlife. Some of it’s real, some not so much. It’s aspirational, and there are many paths to success (or failure, as the case may be).
Most people think of themselves as having an entrepreneurial spirit or not, but it is possible to cultivate it.
That said, the differences between corporate life and entrepreneurship are extreme. Read through the seven outlined below and quickly assess whether the differences make entrepreneurship more or less enticing for you.
If the answer is more, maybe making the leap is in the cards for you this year.
1) It’s True; Flexibility is a Game-Changer
Imagine getting up, working out, taking the dog for a walk, then waking the kids, having breakfast as a family, dropping them off at school, kissing hubby as he heads to the office, and diving into your day.
Not frantically playing catchup to 368 cc’d: emails as soon as you open your eyes, but following your agenda, at your pace, scheduled ideally to match your energy levels in alignment with your values. Imagine focusing almost exclusively on high-value, high-return, next-level strategies, and business initiatives.
Maybe you put in 2–3 hours of focused work, take a client call, and eat lunch outside, before putting in 30–60 minutes in the garden. Then you spend an hour or so working on a marketing campaign, take a break to run to the market before the after-work crowd invades, then create some thought-leader content and post it across your favorite platforms.
You pop in for a quick appointment before picking up the kiddos, catch a webinar on the back deck while they play in the yard, have dinner as a family, and take your time through tucks, enjoying their stories. Then, before bed, you do a little yoga, read something inspiring, map out your next day, outline your next post, and glance at your sales sequence before you get 8 hours of sleep.
There’s something priceless about staying in your zone of genius all day — a limitless, invigorated feeling that supports incredible work. Instead of productivity, you measure output: creative, strategic, business-building output.
Don’t underestimate scheduling appointments and errands when the rest of the world is at the office, commuting, or otherwise engaged. It may seem like a little thing, but all this flexibility compounds to create time. When you aren’t double-booking meetings or scrambling to accommodate demanding stakeholders, your day stretches luxuriously — but only if you claim it.
If you’re building a business for your family — meaning you left corporate for better work/life balance — and you want flexibility and freedom and income and a lifestyle that allows you to be a better parent or more thoroughly enjoy life your way; claim it.
Don’t recreate what you had. Do the thing you said you were going to do.
It will make all the difference. There’s something genuinely evolutionary about consistently spending intentional time with your family every day, without feeling torn, while still trusting yourself to create an incredible business. It adds up to a better you: a more rested, more mindful, more fulfilled, healthier person who can give more fully and lead more successfully because her cup overflows.
2.) Visibility + Authority = Leadership
You may have a team or a co-founder, but for most entrepreneurs, you start as a solopreneur.
While that doesn’t mean you don’t have support, outside influence, or a network to lean on, it does mean that most of the day-to-day decisions are your own. Depending on the size and complexity of your corporate organization, this can be a dramatic change.
In most corporations, unless you are in senior leadership, you’re rewarded for specialized skills and decisions by committee. The better you get at something, the more it benefits your company for you to specialize. That’s not to say you can’t and shouldn’t be aware of how your job fits into the bigger picture, or that you won’t be required to collaborate or lead, but your lane is your lane, and there is almost always a great deal of oversight or even bureaucracy.
In a startup, you wear many hats, meaning that you must choose what actions and roles are going to move your business forward at any given moment. You select a strategy, break it down into tactics, decide what you can accomplish on your own, what to outsource, and somehow identify what you don’t know.
It’s imperative, not only to set boundaries and hold yourself accountable, but also to know your strengths and abilities and quickly assess where you’re headed, what will make the difference, whether or not you can do it on your own, and how long you’ll allow yourself to work on it before you live with the results or move on. They can be emotional decisions.
Any one of those things can take you down a rabbit hole. Who knows where you’ll end up or how many of your minutes/hours/days will disappear?
And you have to commit, you can’t regularly change strategies, or you’ll never build traction.
With no one to run it by, it’s all you: vision, budget, execution. Now, before you turn away from that level of responsibility, know this: If you’ve had the benefit of seeing that level of complexity in action, you know how to re-create it. And, even more importantly, you know how to prevent it.
You don’t have to recreate what you had, and you shouldn’t. Complexity rarely pays off. Build your ideal. Know what works for you, your vision, your clients, and your future.
3) The Upside is Motivating
In Corporate America, there are a few different ways to make significantly more money: 1) earn a promotion, 2) make a lateral move to another organization, 3) start a side hustle.
All these options are limited to some degree. You might have topped out without someone leaving an opening above you in the org chart. You may not see a future for yourself on your current trajectory because the role higher than yours isn’t a good fit. You may not be in a season where it makes sense to take more on or move to another location. Or, your benefits may keep you tied to your current employer, despite fit issues.
There are a lot of reasons for stagnancy, complacency, and perhaps even contentment. Have you mapped it out? Sat down and created models to know the likelihood of ever getting where you want to go?
Most of you haven’t, and it’s not because you don’t want to know, it’s because your hunch is you can’t get there on your current path, and the thought of starting over is too overwhelming. It may feel impossible. If that’s your reality, I challenge you to look at the upside instead of the downside. Measure the gains, not the gap.
How fast could you grow your own business? How many clients would you need to take on? What could you reasonably charge for your services? How much more income is possible to offset the benefits you would be giving up?
Entrepreneurship isn’t a get rich quick scheme; it’s an opportunity to get paid what you’re worth. When you are an employee, your employer expects you to return more than enough value to the company to offset your salary. Many HR departments anticipate value greater than four times your salary. What if you started there? Imagine earning four times your salary as an entrepreneur. What would that mean for your life?
4) Entrepreneurial Work/Life Balance Crushes the Alternative
In the same way that flexibility means freedom, time is relative because the lines between work and life may blur, but in a very different way than work/life balance.
Work/life balance is compartmentalizing your life.
It’s saying, this is how much I can invest in my career before I feel like the other important aspects of my life begin to feel neglected or fall apart. Likewise, it’s saying, this is how much bandwidth I have for my family, health, friendships, or passions before my career starts suffering or takes a nosedive.
It’s a flawed approach because life is not a zero-sum game.
Entrepreneurship is an opportunity to change your approach, to make progress in many areas, but it’s not a given. Many entrepreneurs have the best intentions, but still trade time for money, and continue to get caught up in time traps. For example, if you don’t automate certain aspects of your business, you will be the bottleneck in your business.
The primary way to change your relationship with time is to pick the right business. Don’t underestimate your passion for your work. It’s true what they say about doing what you love and never working another day. It’s work, for sure, but the rewards of the moment and the potential payoffs make it fun.
It’s exciting to dive deeply into what you love, to invest in yourself, to build something, to witness your progress, and create something that never existed before.
The second way your relationship with time can change is by committing to compounding activities. Choose exponential growth, exponential results, and make exponential leaps forward. It may mean tech enhancements, hiring out aspects of your business, learning evolutionary concepts, or hiring a coach.
Even the most innovative, progressive, leanest companies struggle to move like that. As an entrepreneur, you can weave these strategies into the culture of your startup.
5) Choose Your Own Adventure
No matter how excited you are about your vision, how visionary you are, or how ripe the market it for your idea, it will take quality fundamentals to make it happen.
Whether or not you should get some experience before you make the leap is subjective, here’s why it’s not cut and dried: When you’re young, you’re idealistic, optimistic, and you can see solutions in a way that you can’t when you have the experience that comes from challenges, hurdles, and failure.
With age comes wisdom, but also fear — doubt springs from knowing the myriad of obstacles that will inevitably get in your way. You are also more fully appreciative of how much you have on the line.
When you’re young, your anticipation, motivation, and enthusiasm can propel you to great heights quickly. You also know what you know, and you don’t feel like you must know everything about everything to move. You’re agile by default. Roadblocks may pop up, but are not likely to derail you if you have a growth mindset.
On the other hand, don’t overlook the very real, very potent advantages of maturity and expertise. When you’re young, what you don’t know may be what keeps you from succeeding.
With experience, you’ve likely seen what works, what doesn’t, evaluated your strengths, overcame your weaknesses, and developed a broad perspective that makes it easier for you to assess your options in context. You know how to go from point a to point b or even point z without drama, false starts, without wasting time or money.
You’ve probably perfected processes and activities that you can rely on to achieve results that your younger self won’t develop for years. You trust yourself, have strong self-awareness, and have situational-tested skills to apply to your advantage.
So, when it comes to your path, what’s your instinct? Do you have a single-minded purpose, and does confidence come naturally? If both are true to a high degree, go for it now. You can always shift gears or hire experience when it comes to that.
If you want a little seasoning or are looking for a broader perspective, go the corporate route first, but don’t just go to go. Don’t look for a specific compensation package or a brand-name to put on your resume. Set a long-range plan.
For example, what I was searching for in my corporate experience was world-class branding, inspiring senior leadership, global perspective, and client management exposure. I wanted to access opportunities that were unachievable on my own. It was worth it for me to trade my time and talents to get that. But set a time limit. Get what you came for and stick to your deadline.
Corporate is seductive, and getting out may be the biggest challenge of all.
6) Culture Matters in Both Environments
A company’s culture is the sum of all employee’s behaviors, but when you are the entire organization, you embody the culture and personify the brand.
Culture flows from the top, and it starts on day one. Frankly, it starts from when you’re daydreaming about your mission and customer experience. It isn’t just about your behavior, what you stand for, or how you want your customers to feel when they use your product or service; it’s your worldview.
What do you believe about the world, what change do you want your company to influence, and how can you bring to life that vision and transformation through engagement with your brand?
I worked in sports and media for 20-something years. 100% of the organizations I worked for or with had the best intentions — grand visions, inspiring missions, and legitimate plans to be the change. The sports companies were utterly devoted to the game; the media companies were relentlessly committed to the story. Yet, they stumbled along the way.
At times, they lost sight of their why, and their culture became about something else. It happens. The key is to course correct.
Your “why” is a super-buzzy objective and impetus, but it’s also a vital NorthStar for your actions, decisions, and outcomes. Make sure it’s transcendent enough to take you the distance. And re-evaluate often.
7) Break the Cycle of Trading Time for Money
This is crucial. 1) Time is our most valuable commodity, and all the money in the world cannot replace time. 2) Limited time means limited impact. 3) Building authority increases the value of your time. 4) Some aspects of your business must be digital to take full advantage of time. 5) If you don’t know how you want to spend your time, you’ve got work to do.
What are the people, places, passions, and opportunities that light you up? What will you regret not seeing, doing, or experiencing when you’ve run out of time?
I’ve never added it up, but it’s highly likely that I’ve made more than 1 million dollars over the years. But because it wasn’t $1 million in one lump sum or $1 million for one project or creation, it didn’t feel like $1 million. I probably spent some of it wisely. I probably wasted some of it. I was perhaps intentional with some of and unconscious with the rest.
All that to say, earning is less important than value, which is less important than impact, which is less important than time.
Instead of setting up and knocking down income goals, why not start with time goals? Measure experiential milestones or countdown your bucket list.
The way to maximize time is to get to a place where the world rewards you for being you, where what comes easily or naturally to you is invaluable. It’s the only true way to break the cycle of trading time for money.