Overnight Success: 20 years in the Making & 3 Tips to Make it Happen for You

When I created 48 Innovate, it was the culmination of a lifelong dream to run my own business. I knew since my teens that I had enough passion and drive to do it, even if I hadn’t figured out the details yet. But the devil is in those details, and there is a heck of a lot to figure out along the way. The biggest obstacle for most entrepreneurs is money. I’m not talking about startup capital alone. We all need to put food in our bellies, gas in our tanks and roofs over our heads. With the release of my book,
The Innovation Revolution | Discover the Genius Hiding in Plain Sight, I’ve been getting a lot of personal questions about how to make the transition from working for someone else to working for yourself. In this post, I thought I would share my experience because although my last name is Kennedy, I’m definitely not one of those Kennedys.

For working stiffs like me, the road to entrepreneurship has been paved with a lot of sacrifice.

Read on for my best tips on how to step out of the security of direct deposit and into the startup space.

  1. Establish Your Freedom Fund

Unless you hit all the right Lotto numbers last week or have a rich uncle who left you a fat trust fund, you are a slave to your salary and benefits. The fantasy of flipping over your desk, flipping off your boss and making a dramatic exit will have to remain a fantasy for now, unless you enjoy living under bridges. But if this notion of entrepreneurship keeps nipping at you, popping up in your head every time your brain gets a moment alone, perhaps you should begin making long-term plans for a professional parting of the ways (no drama, please!). It’s time to start saving up for your Freedom Fund. Yes, I’m aware that most people use a different F-word to describe it, but I’m from the south and my grandma might just read this.

Saving up six months’ worth of living expenses is a good guideline. That amount gives you enough wiggle room to figure out whether you want to stick with your startup or explore other options. I’m single and live in a reasonably affordable city, so it took me about three years to save up that much cash. It may take you less or more time, depending on your family situation, living expenses, location and salary.

Start by taking inventory of your budget and calculating how much you can put into savings each month. I know, I know…its a miserable exercise. I had an amount automatically transferred from my checking to savings every time I got paid, so I never even considered that money.

Now you’re ready for more sacrifice. Learn to stop wasting your money (another miserable exercise…who said this stuff was easy). Your momma told you to stay away from credit cards and avoid the debt trap, and I’m going to tell you too. I’m also going to tell you to stop spending money just because you have it.

Do you really need that new pair of shoes? Can you skip that fancy dinner out this weekend? Can you cut back on your daily trips to Starbucks? Maybe buying a new mattress is a must-have for a good night’s sleep, but can a new sofa wait another year or two?

I’m not suggesting you don’t enjoy life. I took vacations and still made my mortgage payment. I’m talking about making choices and setting priorities. Instead of going to the mall, I would take that money I would have spent on new shoes and socked it away. Those wallet-sucking trips to Target became less spendy when I evaluated whether I really needed what was in my cart. As I got promoted and made more money, I continued to live on the same budget and upped my savings.

Once you get into the habit of tradeoffs and choices, the Freedom Fund goes from conceptual to tangible. In business, everything is about tradeoffs. Nature has to balance itself, so does business, and so do you. If you want to make unconventional choices, like quitting your well-paying job, then you are going to need a Freedom Fund. And you’re not going to get one by frittering money away. You can have a luxurious life, just have limits.

  1. Have A Dream And A Plan

So, you’ve done the math on your Freedom Fund a zillion times, read all the how-to books, listened to a ton of expert advice and feel ready to go. Great. Now what? It’s not enough to have a vague dream that you want to be the next Elon Musk. You need a plan. For me, I wanted to leverage the 20 years of marketing and sales experience toward my own business. My plan did not include going back to school to become an architect or learning to play an instrument and forming a rock band. I figured I could freelance for a bit while building up momentum and contacts. It took me about three months before I got my first contract, and I’ll admit it was worrisome to watch my Freedom Fund tick down. But even harder was the lack of structure that comes with not having a corporate job.

When I was working for a company, most of my time was spoken for. There was a routine of waking to an alarm, getting dressed, going to work, coming home and doing more work, and fitting life in the spaces in between. The sudden absence of structure was confounding. What do I wear today? Do I even shower? When you work for yourself, there will be days when you may not talk to another person face-to-face. If you have hermit-like tendencies, then you’ll really have to push yourself to get out there and network.

I’m quite extroverted, but it can still be daunting to sell yourself to other people. Just get in your car, go to that mixer and strike up a conversation with one person. The next time, make it two people. Build your own momentum. Create a new structure. Have a plan.

  1. Don’t Be Afraid to Fail

Being your own boss can be one of the most rewarding experiences of your life. It can also be a scary, lonely place. Many of us will make it, but far more of us will fail. The statistics are stacked against you. Maybe you won’t get your business plan off the ground, or unforeseen circumstances may force you to back to your desk job. Don’t let failure send you into a tailspin. Think of it as a chance to retreat, re-evaluate and reset.

I have failed many times at many things. I think it is important to acknowledge that sense of failure, or it will haunt you. Remember that you are your own worst critic, so surround yourself with your support network and talk it out. You need to have the balanced view of others who know your talents, strengths, and weaknesses.

Next, seek out input and advice from professionals who know your business and will give it to you straight. Was there something you could have done differently? Did you simply not give it enough time to work? Is it feasible to try again? A lot of corporate-minded people see entrepreneurs who return to the workplace as people who failed, but I see them as making bank until the next opportunity.

Take a different point of view of failure. Learn from it and redefine what success means to you. I have jumped in and out of desk jobs and startup efforts. (My mental secret to dealing with those bob and weave moves is to look at them as mere tax designations…a W2 vs a W9…that’s all).

And most of all, don’t give up. Yes, failure is painful and soul-crushing, and you’re allowed to wallow in it for 5 minutes. After that, get up off the floor, congratulate yourself for having the guts to go for your dreams, then come up with your new plan.

PS: If you don’t want to sacrifice all that, my book, The Innovation Revolution, tells you how to make the corporate thing actually work. It’s insane to take a leap when you have less than a 10% chance of succeeding. You have the power to influence and change business as usual.

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K. Melissa Kennedy

Chief Innovation Officer, Founder, Intrapreneur. Entrepreneur. Enthusiastic leader and speaker. Teller of truths at 48 Innovate
I spent many years working for and building successful companies. I parlayed that experience into a unique process for harnessing hidden assets inside organizations and turning them into big-idea-generating, $1-billion-revenue-producing resources. (Spoiler alert: it’s the people.) I'm an internationally acclaimed expert, happy to share the not-so-secrets that have led to impressive outcomes for Fortune 100 corporations, major educational institutions, start-up companies and entrepreneurs. Working with companies like Cisco, Lancope, Arby's, Capitol Broadcasting Company New Media - WRAL, PRSONAS, Cranfill Sumner & Hartzog, REVO Communications, Erno Group, Focus Carolina, Madan Global, UNC Lineberger Comprehensive Cancer Center, INZONE Brands, Albright Digital, Spring Metrics and NC State Kenan Fellows.

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