Career Change

Thinking of Pursuing Greener Pastures? 3 Questions Entrepreneurs Should Ask Themselves Before Taking That Plunge

Don't confuse boredom or fear with the need to move on. Instead, stay put, and make that old pasture green again.
Thinking of Pursuing Greener Pastures? 3 Questions Entrepreneurs Should Ask Themselves Before Taking That Plunge
Image credit: Thomas Barwick | Getty Images
Guest Writer
CEO of Marketplace Homes
5 min read
Opinions expressed by Entrepreneur contributors are their own.

To entrepreneurs, the world can sometimes look like a candy shop. Over here, there's a lucrative career in app design. Over there, you've just spotted a chance to revolutionize educational loans. For a creative businessperson, the idea of jumping into a new adventure is always appealing.

Related: 7 Sure Signs Now Is the Time for a Career Change

That temptation is especially strong right now, given the tight labor climate we have, rife with opportunities. Between February and March, 472,000 more jobs opened up in the United States, according to the Labor Department.

These conditions make the “grass is greener” paradox seem almost ubiquitous for entrepreneurship: After all, from from a bird's-eye view 1,000 feet up, every new venture looks great, especially if it's in a trendy area like tech.

The reality check, however, comes upon closer examination of the people, systems and processes that probably made you weary of your own project in the first place. Me? I learned this the hard way.

How I lost almost a million dollars proving I'm not a tech executive.

I remember well how "greener pasture" syndrome got to me. I had noticed all the tech companies springing up around me and became green with envy. I thought to myself, I can do this, too, and then I can claim all of the value that comes with technology assets.

That's how I happened to leap into product design for an app to help homebuyers and sellers. We spent over $1 million hiring a seven-person development team to build the app. But it turned out that we could have saved probably $900,000 if we had simply outsourced a lot of the production. Of course,we couldn't have claimed that we were, and are, a technology company -- but we would have saved $900,000.

Related: Thinking About a Big Career Change? Ask Yourself These Questions.

In short, you don’t have to completely pivot to enjoy variety and spontaneity in your career. By seeking out collaborative opportunities outside your wheelhouse, you can supplement your main mission with corollary adventures that inform and enrich it. Here’s a list of questions to ask yourself before you give in to your itchy entrepreneurial feet:

1. Would your fifth-grade self kick your butt?

If you’re feeling unsure, check your origin story, and see whether the move makes sense. Consult your inner fifth-grader: Would that crazy kid be mad at the thought of your starting a catering business? If so, you might be looking too far outside of yourself and your skills.

If, in performing this task, you find yourself struggling to tune in to your fifth-grade dreams, talk to your parents or siblings -- they're the ones who knew you before any money and success you've had came on the scene.

Richard Branson, for example, has said he turns to his mother to keep him grounded. She reminds him of the natural gifts and inclinations that he showed as a child. “As you grew, you perpetually had some crazy new scheme or other up your sleeve that you were convinced was either going to change the world, make lots of money or both,” she wrote in a letter to her little future billionaire.

2. Is money your main motivator?

Money doesn’t tend to strongly correlate with career happiness. Sure, you might need to cross a certain financial threshold in order to make your plans a reality, but once you're past that threshold, pay level isn’t significantly tied to satisfaction, according to a study published in the Journal of Vocational Behavior.

If money is the driving factor, see whether you can make your existing project more lucrative or add a side hustle that complements rather than complicates it.

3. Are you just burned out and bored?

Into every career a little fatigue must fall. But it’s vital that entrepreneurs not confuse fatigue for a lack of passion or drive. Feeling tired doesn’t mean you should pack up your lifelong purpose and try something else.

Rather than jumping into a new field, consider trying strategies that will lessen your fatigue. Try shifting responsibility for some of the smaller or more technical tasks to someone you trust on your team. Maybe you’re feeling bored because you have become too much of an expert at your job and need to challenge yourself in a new way.

There have been moments along my own 12-year journey when I’ve doubted my dreams because I’ve been drained. The chores and disappointments of business have sometimes seemed crushing -- I didn’t want to face another tax day or another meeting.

But had I given up on my ongoing project for what I thought were greener pastures, I would have found myself still entangled in those same weeds, just in a different place.

Related: 5 Entrepreneurs Who Changed Careers at Midlife and Triumphed

Getting excited about new opportunities is not a bad thing -- in fact, it’s probably a sign that you’re a natural-born entrepreneur. But amid all the noise of opportunity knocking, stay tuned into the passion and talent you started with. Don’t confuse fatigue or fear with the need to move on. Make the old pasture green again by investing in it and reinvigorating it until it feels like new.

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