Career Advice/ Entrepreneurship

5 Things You Should Do Before Quitting Your Job

resume and laptop on a desk

It’s here –the day you take the leap into the wild and wooly world of entrepreneurship, leaving behind the security and stability of a “normal” job.

The leap is thrilling.

It’s also completely terrifying.

 For myself, there were many nights during Year 1, Year 2, and a few in Year 3, where I laid awake wondering, “What in the @*&% did I just do?”

Looking back, there were several key actions I should have taken before quitting my job to go full-time in my business. They say hindsight is 20/20 – well, maybe a few aspiring entrepreneurs can glean some wisdom from the things I wish I’d known.

Here are 5 things you should do BEFORE you quit your job to become an entrepreneur:

Try your idea out. 

I recommend at minimal “trying” your business idea out for at least six months by burning the midnight and weekend oil before you turn in your resignation letter.

Good news is that this straddling the fence, business idea test period is easier than ever, thanks to the internet and the emergence of the gig economy.

 For most companies – product or service – you can at least get your website up and test the market with your idea. Invest a couple grand into promo and see if the fish bite. If they don’t bite after a couple weeks or months, you may want to take your idea back to the drawing board and do some tweaking while your day job still covers the bills.

Got a product to sell? Put something up on eBay or Etsy.

Got a service to offer? Start offering your services on freelancing websites like Thumbtack or Upwork.  

Create a website, social accounts, and some decent branding. You don’t even have to take work that comes your way – just gauge the response.

If the fish don’t bite, either move to a different pond or try a different bait.

Business is really that simple (okay – maybe not that simple…).

Get a backup plan in place.

Okay, for many of us young entrepreneurs this translates into identifying which friends will let you couch surf (don’t worry, Mark Cuban did it).

It’s always nice to have a backup plan in place. Whether or not you actually have to use it, for some it eases the mind and allows them to focus more clearly on the task at hand (i.e., growing their business).

There are a variety of ways you can get some sort of backup plan in place. For me, it’s always been securing an additional source of income for 12-18 months of starting a new business.

As a marketing and public relations professional, I knew growing my own client base from scratch was going to take a while – like a couple years “while”. This wasn’t a pessimistic timeline, it was a realistic one for my industry and location. Corporate connections and contracts don’t happen overnight.

To help ease the pressure off my baby business and its infantile revenue generating abilities, I picked up a couple side gigs that greatly alleviated my would-be cash flow issues – I taught adjunct at a university and became a part-time subcontractor for a big advertising agency. Neither of these positions drained me or stressed me out; instead the extra cash they generated let me focus the majority of my energies on my fledgling company, and allowed me to say “no” to bad projects and bad clients that would not have been a good fit for my brand.

Securing side income or bridge jobs is nothing to be ashamed about. We all do it…okay, okay –trust fund babies (Jared Kushner, I’m looking at you) don’t do it, but enough bashing on those born into privilege, or as Warren Buffet put it, those that won the “Ovarian Lottery”.

Learn on someone else’s dime. 

A lot of entrepreneurs will work in their desired industry prior to striking out of their own and its’ a great way to minimize risk, stress, and get you more prepared to take the entrepreneurial leap and soar on the wings of success vs. go splat on the sidewalk below.

Learning on someone else’s dime can be a great way to minimize your cost of education while getting the experience necessary to succeed on your own. Such intern opportunities can be super helpful, especially if your chosen business involves technical or trade aspects that may not simply be developed from reading a guidebook or talking to others (applies to most businesses).

In a 2015 interview on The Motivated Millennial Blog, Barrel Backers Co-founder, Adam Rivette, stated, “Learn as much as you can from others before jumping in and starting your own business. It’s not as glamorous as current news sources would have you believe, but if it is your calling, then there’s no better place to be.”

Go work for your soon-to-be competitor. Land an internship. Find a hiring company that’s in the same space as your proposed entity. This isn’t an act of corporate espionage; it’s simply strategic recon. You aren’t scouting out competitor’s secrets – you’re gleaning tips and tricks to what may and may not work. Approach this type of industry experience as you would a buffet – take what looks good and apply it to your own business, pass on all the rest.

Get a mentor, like, now.

Working with a mentor was a total game changer for my career.

My mentors opened doors that seemed locked shut, provided objective perspectives leading to simple solutions to (formerly) complex problems, and empowered me to reach heights that would have otherwise been unattainable. Whether I’m struggling to manage difficult employees or needing tips on handling gender biases in an all-male industry, my mentors help me navigate unchartered waters

Every entrepreneur – including you – needs a mentor (or two, or three). You need them today, when your business is just a barely more than a “may be good” idea, as much as you will when running a multi-million dollar empire. Mentors can help you navigate a business world filled with landmines, guiding your every step closer to success.

Finding mentors didn’t come naturally to me. I was never the teacher’s favorite, star student, or even coach’s pick. I was always “that kid” – the oddball freethinker somewhere between rebel without a cause and mad scientist that incessantly asked, “Why?” However, as my entrepreneurial career progressed, I knew I had to find someone to help me “figure this thing out”, so I researched more experienced trailblazers and starting asking these admirable peeps to mentor me.

It worked.

I just wish I’d done it sooner.

Don’t wait till you have a big business going to find a mentor. Working with a mentor could be the difference between building a big business and having no business.

Good news: mentors are more accessible now than ever before. Find someone whose career you admire and reach out. Better yet, hire a reputable entrepreneur coach (just google them – there are tons). It’ll be money well spent.

As you’ll learn, entrepreneurial success is never a solo venture; even for those of us that don’t like people much. Successful entrepreneurship is made possible by the collaboration with others. Don’t John Wayne it and try to go solo.

Surround yourself with successful peeps and move forward with their experienced guidance and support (from Day One).

Prepare yourself for the unexpected. 

Starting your own business is tough; it’s way tougher than starting 99.999% of new jobs.

It’s a lot of risk and responsibility.

I remember the first week of running my own business; not in my entire career had I ever made that many decisions in five short days. It can be utterly exhausting. There’s little structure, and essential no guidance – at least not in comparison to that experienced as an organizational employee.

Don’t underestimate the energy that will be required of you over months following “the leap”.

It’s gonna be emotional, tough, and uncertain; and will require you to be the “best you” you can be.

This means healthy, grounded, objective.

The best thing you can do for your business – in all stages of growth – is to take care of yourself. Don’t go into starting your company with momma drama on the calendar, or utter and complete exhaustion from years of mind-numbing employed work. Before launching your company, take a break – even if it’s just a weekend by the lake with no Wi-Fi- and prepare yourself for the intensity to come.

Whatever you need to get your mind, body, and spirit-centered prior to launch date – do it.

Totally okay if you can’t spring for some mountaintop spa retreat (use that dough for your startup capital!) – take advantage of the resources you have at hand. Once a year, I take a week and do a deep dive into my favorite spiritual discipline – reiki.  A pilgrimage isn’t required, just a quiet, peaceful place and $20 course off Udemy or $2.99 Kindle download.

Darwin could have forgone his Galapagos Island excursion and proved natural selection through business, as entrepreneurship is very much survival of the fittest.  Some will succeed, others won’t.

While there’s no surefire formula to guarantee entrepreneurial success, we can stack the odds in our favor by preparing to succeed rather than failing to prepare.

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