A Quick Start Guide to Being a Job-Seeking Entrepreneur

by / ⠀Entrepreneurship / January 9, 2014

“Oh, you’re an entrepreneur? So…have you ever thought about getting a job?”


The chances are high that you’re responding by shaking your head to the point of whiplash right now. Join the club because you’re not alone. With terms in mind, such as J.O.B. meaning Just Over Broke, it’s no wonder that you may have an awful taste in your mouth about working for anyone other than yourself.

The entrepreneurial exodus is now, as you might have already noticed; and the lifestyle, the allure of financial freedom, the career envy you might have hoped to spark, the thought of a workday meaning that you would be sipping drinks on a beachfront–it’s an attractive prospect for these out-of-the-box thinkers who want to overcome the woes of a cracked economy.

…But what if your porcelain delicate dreams also got cracked in the process?

What if you’re an entrepreneur and you still can’t seem to shake the shackles of financial stress or, yikes, outright failure?

What if you have now found yourself facing the prospect of leaving the cozy home office only to go back to a cubicle-shaped prison? What if you are down to your last straw and now all those people who were once supposed to envy you are now coming to collect their I-told-you-so invoices.

Welcome to the contradictory lifestyle of being a job-seeking entrepreneur or, hopefully, an employed entrepreneur by now.

The good news is that you’re most likely just where you need to be. The even better news is that you can still do what you are passionate about doing without as much sacrifice as you might think. The only thing you will need to let go of is your care about what people think. Even in your ideal life, naysayers never stop saying nay. (Let’s call them horses for now.)


Career Tips for the Entrepreneurial Job Hunter

What is Your Current Work Situation?

Firstly, let’s examine what kind your entrepreneurial background because not everyone’s situation looks the same:

  • Some of you may have been grinding for a while to make a new venture work without much success. It could be about time to throw in the beach towel and go get a “real job.”
  • Some of you may be trying to go the opposite direction, but you’re still stuck in the loop of the job search. Heaven forbid if you’re taking on any and all kinds of work just because it comes up.
  • Some of you have probably been going at this for a while, but then all of a sudden something came to a halt in your venture.
  • Some of you may have the case of job-itis so badly that you could collect a disability check.

Your situations might not look the same, but you had better believe that you’re underlying fears and the questions behind them are probably not all that different:

  • Is my service, business, or skillset irrelevant? Is it outdated?
  • Am I not trying hard enough?
  • If I’m going to be working, how can I maintain the work-life balance on top of still trying to do something I enjoy?

Getting in the Game

If you are among any of the entrepreneurial-minded people who oppose the working life, you can start acting like everything is now a game. A game of survival? Yes, that counts too except that this time there are no reality television show producers giving you water and refreshments behind the scenes. Wouldn’t that be nice?

Your livelihood is a serious matter, but changing your mindset to think of your work like a game can help open up a creative part of your brain to a new realm of possibilities, not to mention that it could keep you in a positive state during an adjustment and possibly uncomfortable process.

If you make the game up, you can set the rules and parameters.

For instance, you have the authority to decide which kinds of jobs that you take on. Ask yourself if taking a part-time retail job will help you meet your ultimate goals. Working at American Eagle might benefit someone who eventually wants to be a personal stylist, but not so much for someone who wants to do IT consulting.

On the other hand, these types of low-paying and entry-level positions could be  counterproductive for someone who has already made significant professional advancements. That does not make it a completely bad idea to take on a side job temporarily, but if that source of income ends up being less than a living wage, or if it turns out to be a time and energy suck, then it could backfire.

No matter what capacity you are or will be working in, you’re on your own Candyland-esque trail of self-fulfillment. Each step you take is the result of deliberate–and sometimes risky–action, all of which keeps you moving forward towards the delicious reward.

SkillStorm proposed on their blog that the career ladder needs to be views as the career jungle gym instead. Here is an excerpt in which they explain the metaphor:

Ladders are linear with only one distinct path to move up. There is a single trajectory here, which can be very limiting….You see, taking the jungle gym approach allows you to still reach the top, but it also allows you to be strategic and flexible and come up with different approaches and choices on how to get to that desired destination.

(Brownie points to anyone who immediately thought of Chutes and Ladders. See? You’re on track already.)

New Ways of Thinking About Your Job

Instead of despising your new employer or employer-to-be, think of the person or company like you would a venture capitalist willing to invest in your enterprise. This is a particularly good mindset if you’re continuing to work on your own “real job” at the end of the work day.

You may be looking at a job listing or a company who needs your service (they just don’t know it yet, right?). It doesn’t matter what they label your work up front or what paperwork they plan on having you fill out. You can still pitch yourself as a contractual employee or even consultant. Freelancers know what this is like all too well.

The potential problem with pitching for a paying assignment in this way is that the gig might only last temporarily. Don’t let that stop you. If you do good work, which of course you do if you care enough to read through this article now, and if you build relationships while you’re there then you could have yourself a loyal customer in the long run.

Patty Orsini of TheLadders recommends using your resume, portfolio, job interview and any other professional resources as a means to display your strongpoints even if you owned your business at one time. It would be no different talking yourself up as your own boss as you would if you were going in for the job in a traditional setting.

Final Tips

  • Find a colleague or friend who you can depend upon for support during this transition. A fresh set of eyes, a dose of compassionate advice, and a listening ear will be more valuable than you might think.
  • Don’t neglect social media. LinkedIn is going to be one of your closest allies on this front. Make sure that your profile is updated with a good headshot of yourself, detailed information about what you accomplished in your previous work or businesses, and links to any sites you may have. Recently, they made a portfolio feature available that enables users to upload documents , images, and other files that make up their body of work. Artists, branding experts, graphic designers, and writers should really make use of that feature.
  • Read books and study up on other successful entrepreneurs. They all started somewhere just like you did. Go a step further and tweet them on social media granted they are still around. There are a lot of personable and approachable individuals with priceless business wisdom, and they’re just the click of a button away.

Hopefully, this guide has gotten you back on track and at the very least it has given you some new methods to apply. If you have any other ideas about what makes a successful job-searching entrepreneur, please leave a comment. Share this with your entrepreneurial friends as well. You may have more in common than what it seems

Happy searching!

Sandra is a Creative Business Writer as well as Internet Marketing and Verbal Branding Strategist who shares digital media and marketing strategies in her blog and newsletter. She has developed a project called {CONNECT}, and this helps owners of small businesses and virtual companies manifest the visions for their businesses successfully and with strong, marketable content. Beyond spreading her thought leadership about social media and digital media, she enjoys creating artwork, doing yoga, reading, and cooking.

Image Credits: tekkek.com, increasinggrace.blogspot.com

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.