How to go from a job you hate to a business you love

Lisa Lewis Miller
8 min readOct 16, 2018

Do you know this person?

They’re the kind of employee used to getting promotions regularly — if not every year, then every other year. The kind who’s has no problem zooming right up that corporate ladder and keeping up with (or outpacing) many of their peers.

And the kind of person who is craving more from their career and is secretly, desperately itching to jump off that ladder. They know that their corporate success shows that they could totally be successful out on their own as an entrepreneur. They’ve got the skills and the drive to make it happen.

If this person might actually be you, listen up.

Ambitious and analytical individuals like you looooove the idea of entrepreneurship because you can see the market opportunity, know the stats about solopreneurship (did you know that there are more than 35,000 single-person businesses in the US making over a million dollars each year?) and you may or may not have whipped up a business plan draft in Excel for fun on a Friday night.

Your soul might be begging you to try entrepreneurship if you’ve been binge listening to podcasts like Being Boss, Online Marketing Made Easy or The Diva Business School on your commute, creating your own DIY MBA on building a business. Or maybe you know you want to be an entrepreneur because you research different corporate structures on LegalZoom for fun in your spare time (and now know more about tax law than your accountant), or sign up for oodles of online entrepreneurship classes like Pat Flynn or Ramit Sethi.

It’s true that running your own biz can be a fabulous option to help you pivot your career and use your strengths to get more aliveness and fulfillment out of your work.

But I have a truthbomb for you. You need some serious tough love to help set you up for success in the long run.

It is… you might not be ready for entrepreneurship. Yet.

Ugh, I know, the truth hurts. Especially when the idea of entrepreneurship feels like the exact parachute you need to escape a less-than-ideal work situation.

But while your heart might be aching for the freedom of working for yourself, your brain…well, it might just go into risk management overdrive when you even start to think about making a bold change like working for yourself.

(Yes, even if you’re an ambitious, analytical, go-getting Type A to the max.)

Taking the leap into the uncertain world of entrepreneurship is scary, so it’s normal that your fear would be trying to pull your brain’s emergency brake as fast as humanly possible.

You might recognize these fear-filled whispers from your inner self-doubt gremlin:

“What if you quit your job today and don’t get any traction in your entrepreneurial endeavor, go completely broke, liquify all your investments, have to break your lease, and move back in with your parents?”

Or worse:

“What if you put so much pressure on your dream that you suck the fun right out of it, and entrepreneurship becomes even worse than working for someone else?”

These fears make total sense. The stakes of what’s at risk are high!

Your inner project manager (you know, the inner voice that’s all, “We’re over budget on lines 2, 7, and 12”) wants to keep you safe, and it’s telling you that being an employee seems a lot more stable and secure than entrepreneurship and might feel like the “responsible” thing to do when you have a spouse, a mortgage, or kids in the financial equation.

But settling into the safe, known, comfortable path for the rest of your life is buying yourself a 1-way ticket to Complacency and Boredom-ville, USA. You don’t want to live the next 30 years crawling out of your skin,knowing you’re capable of more and never giving yourself a chance to find out what you can really truly do.

Before you find yourself on your therapist’s couch talking about this overwhelming wave of entrepreneurship guilt, let me share a secret way to pave the road to entrepreneurship that balances the risks with financially responsibility.

It’s called a “bridge” job.

In the book Pivot by Jenny Blake, a “bridge” job is defined as a new job, usually working for someone else, that moves you toward your dream of entrepreneurship by letting you hop to a directionally correct lilypad — the one that’s right between full-time employee and full-time entrepreneur.

What’s amazing about a bridge is that it allows you to get paid (with the stability of a predictable paycheck, plus health insurance and all those other helpful benefits) while you’re acquiring the skills and resources you need to go full-time in your new business. And, if you play your cards right, you can set boundaries on your bridge job time that also allow you to start building your new business deliberately and methodically on the side.

Even more amazing? You’re not putting a ton of pressure on your baby business to become your full livelihood overnight. You’ll have more fun building it slowly part-time until it gets to the revenue you need to transition your employment to part-time (or leave the working world completely)!

There are tons of ways to create a satisfying bridge job:

  • Leapfrogging into a job similar to your current one but in the industry you want to become an entrepreneur in,
  • Moving into a new role in your current organization that equips you with more of the knowledge, relationships, or skills that you’ll need to work on your own one day,
  • Pulling what Emilie Wapnick coined an “Einstein” in her work on Multipotentialites: move into a job that doesn’t require 100% of your brain or energy so you can lean back from your 9-to-5 and lean into building a side hustle in your 5-to-9,
  • Transitioning into different/alternate working hours, whether going for four 10-hour days or moving into official part-time work, to free up more time and space to build your business.

Not taking a dramatic, sudden leap into full-time entrepreneurship isn’t boring: it makes good financial sense and manages risk. And, it also helps you set the precedent of choosing a path forward in your work that feels good to you (and takes care of you). When you’re the boss full-time in your new business, you want to feel like you have lots of tools in your toolbox to take strategic and calculated risks rather than feeling like your transitions are gigantic and dramatic.

So you’re sold on the idea of a bridge job. But now the question becomes: How can you create (or find) the magical ray of sunshine bridge job that fits your needs?

And that’s a tricky question.

Designing a great bridge requires you to dive into the self-awareness swimming pool headfirst. Your mission is to move into a job that’s more fun for you, that is helping cross-train you for your future business, and that allows you to draw the boundaries you need to keep feeling energized to build that company on the side. Which means you’ve got to have a vision of the business you want to build, so you can tell if a potential bridge is directionally correct for you or not. (So if you’re passionate about nutrition, getting a bridge job working at Frito Lay may not be the right fit for you.)

If you don’t know what kind of work feels good for you — or can’t totally see the skill gaps you’re wanting to fill yet — finding a solid bridge job will be harder than nailing crow pose in yoga.

So the first step toward both identifying your bridge and coming up with business ideas that would be fun for you is mapping your strengths.

Moving into a job that doesn’t use your strengths is a recipe for burnout and frustration — and building a company that doesn’t leverage your strengths is an even worse idea for your happiness and business sustainability. (So if you’re wanting to build that nutrition coaching business, and have a gift in 1-on-1 conversations, don’t sign up for a bridge job doing email-only customer support.)

To make sure you aren’t headed for a recipe fail, you need to know how to identify your strengths — and mapping them is easy as 1, 2, 3:

  1. Notice moments in your day where you find yourself in a state of Flow. Flow is a term that psychologist Mihaly Csikszentmihalyi made famous in the 90s describing when you’re so immersed in work you can’t help wanting to dig deeper, research more, and create a more fabulous product. You’ll know you’re in flow when you’re working on something and, before you realize, it’s 11 o’clock at night. Get curious about what makes certain activities fun for you. If you loathe explaining your branding strategy document to others but love doing the research to create it, your strength might lie in diving deeply into data and translating it into written words. If you enjoy sitting with a colleague to teach him how to run a report in Salesforce but hate running the reports yourself, you probably have a gift for teaching. For every area where we perceive weakness or struggle, there’s usually a corresponding area where we flourish and shine. Seek out the shine spots!
  2. Look for (constructive) external feedback. Pay close attention to the things that people ask you for help with, seek your advice on, refer to you as the expert in, or give you compliments on. Those traits are things that observers notice and that distinguish you from your average corporate Joe. You may not think that traits like being warm and welcoming are necessarily strengths, but when you get that feedback from others, it means you’re doing things differently than the typical employee — and it shows. Who knows: your friendliness and ability to put others at ease might make you a fabulous CEO of an event planning company (or the founder of a boutique onboarding and training consulting service) one day.

Your strengths are where your superpowers lie, so knowing them is the foundation of your success — both as an employee and as a budding entrepreneur.

That means, you absolutely MUST use your strengths to find that great bridge job and future business idea.

If you don’t, you might end up right back where you started: frustrated, burned out, miserable, hating your job, or hating your job. Finding work right now that’s fun for you and uses your strengths will help you pave the path (or build the bridge, as it were) to what’s next so you’ll never look back.

Now, it’s your turn! Add your response below: If you could create any business, what would you start? And what kind of a bridge job would be most helpful (and most fun!) to keep you moving forward towards it?

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Lisa Lewis is a career change coach who helps unfulfilled individuals create lucrative, soulful, and joyful new career paths. Don’t love your job? We should talk. Learn more at GetCareerClarity.com or check out The Career Clarity Show podcast on Apple Podcasts, Stitcher, Spotify, and Google Play.

Found this article super juicy — but want more than just a taste of information about your strengths? For help with holistically mapping your strengths, interests, and personality to build the business (and bridge job) that fits you, check out LisaLewisCareers.com.

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