• email
  • Tumblr
  • Reddit
  • StumbleUpon
  • Digg
  • LinkedIn

I’ve heard the question, “What should I do?” a lot this month. Between reader emails, “Should I focus on my passion or make money first?” or friends, “Should I keep building my business or take the dream J.O.B?” The anxiety that comes with these Big decisions isn’t lost on me.

Last month I polled close friends about a business decision that had plagued me for weeks. “Hear me out and tell me what the hell to do!” I said. They know the drill by now (to ask smart questions) but for weeks I ran around hesitant, afraid, and unsure before I was finally able to decide.

All of us have Big Life Questions that force us to pause and reflect.

We doubt, we hesitate, we get excited. The very act of deciding causes discomfort because to feel like we’ve made a good choice, we first have to turn off the world, #1 hijacker of our thoughts. Laundry, to-do lists, bills, tweezers, your boss – these have no place in real decision making.

Add in self-doubt and genuinely hard circumstances – a new phase of life, a break up, family drama, business transition, new career, grief – and it can feel near impossible to make a decision.

Deciding requires enormous courage. @ishitagupta (Click to Tweet!)

I wrote a book five years ago compiling lessons I’d learned from being at the Big Life Choices crossroads for over a decade. Career decisions, relationship choices, The Guide To Making Hard Decisions is the framework I used to help me decide. If you want to get clear, real fast and real good-like, download it now for free.

Today I’ll share new lessons I learned in the last few months of decision making in my life. I’m always learning new ways to optimize because: New level, new devil, as they say.

If you check out the ebook and these lessons, and then ask your friends to ask you smart questions, you’ll be on your way to making good decisions sooner than you think.

How to decide (version 2.0 of many more to come)

1. Can the decision be an “AND” instead of an “OR?” My friend Al told me that often we believe a decision has to be one or the other, without giving ourselves the option to have both. In our panic to decide, our vision narrows and we only look at our options in one way. “Is there room to have both?” he asked me, “But maybe not at the same time?” It was brilliant and instantly pulled me out of the claustrophobic One Right Answer syndrome. When I thought about it realistically, I could totally have both if I waited two months, which helped reduce the boxed-in feeling I felt earlier.

2. Most decisions are reversible.
Al (bless his heart) also told me not to worry because more often than not, choices are reversible, we just have to believe it’s so. Unless you’re talking surgery, when what’s done is done, there’s nothing you really can’t go back to and say, “You know, I don’t like X anymore and I’d rather have Y.” You might have to wait, you might have to compromise some quality or other elements, but you can go back and change your mind.

3. You feel loss more than you feel gain.
Whenever something’s on the line to lose, we feel it ten times more than what we gain, even if what we gain is amazing. It’s human nature to hate losing because we have to let go of our attachment to that thing. My friend had the option between a dream job with everything he wanted: flexibility, security, great pay, industry relationships. But because he felt he had to put his dreams on hold in order to take the job, which meant never being able to pursue his dream again, he was freaked, even though he knew it felt right. “But it’s a stepping stone that’ll enhance the skills and contacts you need for your dream. You’re not losing your dream, you’re gaining amazing resources and experience to pursue it!” He breathed a sigh of relief. Once he got permission to keep his dream alive, seeing how this job was also good for him was much easier.

4. Is it temporary?
The reason we freak when making decisions is because we think our choices are final. Like #2, choices you make today are temporary and based on today, not forever. You are not locked into a decision even if it feels permanent. Even things we usually think are forever – marriages, careers, houses, are not. There’s flexibility in these choices even years later, and your energy opens up when you stop thinking in finality. I told my friend to see his job as a stepping stone into the next phase of his dream and he realized he didn’t have to do the job forever, just until he wasn’t learning anymore.

5. Use logic AND emotion. KNOW YOURSELF.
Smart decisions use both logic and emotion. In order to use them you must KNOW YOURSELF. I’m logical but far more emotional/intuitive. Most of my great decisions – professional and personal – were made with “I think this is right” and “Man, this feels right.” In order to do that, know what you need. Earlier in my life I needed more structure and challenge – where I learned and was tested. Working with Seth Godin, running my business, and disciplining myself to set a proper schedule served this purpose. But now in my life I need more ease, simplicity, and wayward dreaming – the space to do what I want without the order and structure I genuinely needed back in the day. And sometimes I need both!

Knowing yourself helps you not delude yourself and actually give yourself what you really want, instead of what you think you want.

6. Trust and have faith in yourself and your abilities.
This is a sine qua non for every part of life, really, especially if you want to be successful. Part of deciding well is not giving into fear that choices and opportunities in front of you right now will go away if you decide “wrong.” Remember, YOU created these opportunities in the first place and will do it again when you need to. Don’t fear. It’s hard to choose now, but YOU called your options in. Let this give you hope and relief that you’ll do it again, even if you do screw up now. Which you won’t.

7. You already know the answer.
Even if you genuinely believe you don’t know the answer, you do. Your body does. Trust the small signals it gives you and listen to it. When you’re deciding, simplify your life and get back to natural signals – body, heart, nature. Do things that allow you to feel in your body and connect to it so that you start to hear its wisdom. Personally, yoga answers a lot of my questions as does walking in the sun. Your body will react to things so that you don’t have to fake the funk – if it’s that hard to say yes to something and you feel your body close down, it probably means you should say “no.

8. Get support and the right people on your team.
This is a big one. All of us have friends we talk to when we need help. What you’re looking for are the one to two friends who prioritize your heart and understand what you’re up to. There’s no agenda like there is with close friends or family, who even though they love you (and God love them) don’t know the nuance behind Big Life Choices. You want people who’ve been on or are on the same journey as you. I called:

    • my younger brother because he believes in me and wants to lead an excellent life too
    • my friend Al who’s in the trenches with me and knows how to ask questions
    • my friend Sacha who’s in the trenches and knows my heart and affirmed my heart
    • two women who’d made the exact decision a few months earlier that I had to make now

It’s important to take advice from only the realest and best people otherwise you’ll get burned (from experience.) It’s not enough to “sift out” sh*tty thoughts someone feeds you – part of being successful means you carefully select the people, mentors, books, advice you consume. Find people without opinions, but who ask smart questions, reflect back your reasoning or question it, or people who straight up love you, “It’s tough, but you’ll figure it out.”

xx Ishita


Ishita Gupta is an entrepreneur, speaker, and business breakthrough strategist. Building her business from zero to multiple six-figures in one year, Ishita helps entrepreneurs get the confidence they need to run their businesses like a Pro. Her programs help business owners lay foundations to make money, create systems to increase productivity, sell with confidence, and do high-impact marketing that gets results. Ishita speaks at conferences around the U.S. on entrepreneurship and leadership, including World Domination Summit, TEDx Detroit, Columbia University, and more. You can also follow Ishita on Twitter.

Image Courtesy of kelsee.