5 Ways to Evaluate Tough Career Decisions

[Editor’s Note]: I wanted to write this post over a month ago, when the emotions were raw and visceral, but I haven’t had a lot of free time since then and this has been a laborious and terrifying post to write.


Our new apartment doesn’t have ceiling tiles so I counted the number of mini-blinds, anything to calm my racing mind. A couple of hours before, I’d hit send on an e-mail “verbally” accepting an offer to work somewhere else. Somewhere that wasn’t MD Anderson (i.e. the first place of employment that I ever truly enjoyed).


If you’re curious, the timeline looks something like this:

Sunday, June 9th, 6:00pm – My wife and I returned from our honeymoon.

Friday, June 14th,  2:27pm – I received a note from the co-founder and President of a local sports technology company aiming to transform the world of endurance sports.

Saturday, June 15th, 3:00pm – I interviewed with this local sports technology start-up, mostly out of curiosity.

Sunday, June 16th, 3:00pm – I blogged about the Case for Entrepreneurship. Trying to convince myself, perhaps?

Monday, June 17th, 8:30am – The  start-up made me a really fantastic offer to be their Director of Marketing.

[Insert INSANE amount of contemplation here.]

Tuesday, June 18th, 7:00pm – I get home from work completely frazzled and overwhelmed. My (new) wife is out on our balcony drinking a beer. (I’d finally drove her to drinking). There was a 12-pack in the fridge for me (to calm my anxiety, to celebrate?) and I (we) needed to make a decision tonight.


Between Monday morning and Tuesday evening I’d used every second of my free time to research the start-up, their product suite, the market viability, how start-up compensation typically works, and much more. I talked to my wife, my parents, my best friends, local (successful) businessmen and my mentors ad-nausem.

Here were some really helpful resources on start-up compensation, by the way:

I made pro and con lists and I weighted each item on each list. I spent 2 full days not eating or sleeping much at all. I had yelled, cried, practiced gratitude and likely given myself a stomach ulcer all in the course of 48 hours. Suffice to say I had searched the depths of my soul for a decision and I’d finally made one and hit send.

I felt relief for a couple of hours. My wife and I watched an episode of The Wire before bed. All these smart, trust-worthy people told me I’d feel relief once I’d made the decision and yet, just a few hours later I was counting mini-blinds and my head and heart were both going 90mph.

The harder I tried to calm myself down, the worse it got until finally I had a full-blown panic attack; the first I’ve ever had.

WHY? Have I made a mistake? This must be a sign.

I hadn’t signed anything yet. I could still say no.

Maybe this entire process just taught me that I had it better than I thought at MD Anderson. Maybe the little things that had lead me to gradually start complaining more and more often weren’t that bad. (See: they weren’t).

Maybe this entire process opened my eyes to just how good I had it at MD Anderson. I worked with great (and really smart) people on projects that aligned with my passions. I believed in the organization’s mission. Maybe I was getting a little restless, but I had all I needed, including fantastic benefits and more PTO than anyone my age ever deserves.

As much as I wanted to be that entrepreneurial-type who took a shot. As much as I’ve told you to take the shot and as much as I believed in the case for entrepreneurship maybe, just maybe, I was a poser. Maybe as bad I wanted to be that risk-taking person, I just didn’t fit that mold. And maybe I’d learned that as I navigated the decision. And that would be okay.

I’d go back to MD Anderson and I’d work hard during work hours, but I’d stop staying late. I’d actually use some of my PTO to do things I enjoy: consult, read, rest, workout, visit family and friends. I’d work even harder at practicing gratitude. I’d get frustrated less. I’d stop worrying about getting a promotion and just keep mindfully doing the best work possible. I’d meet, and take to lunch, even more people throughout the institution.

After all, MD Anderson had rescued me from an unsatisfying job and (for awhile) it’d made me really, really happy professionally. It was a feeling, that prior to my stint there, I wasn’t sure was possible. I owed it to the organization, to my co-workers and to myself to tough out the dip I currently felt like I was experiencing at work.

Ah, there was that relief I’d so hoped to feel. That comfort.

I finally went back to sleep. The next morning I woke up knowing what I needed to do, but I was still uneasy. I’d already told the start-up I was coming to work and I’d been relieved and excited for my next challenge when I’d hit send, but then the panic attack happened and I never wanted to feel that way again. I’d realized I was just being an entitled and ungrateful employee and I was going to stay at MD Anderson.

Regardless of my final decision, my wife said she wasn’t leaving for work until I made a decision. She’d said she was proud of me the night before when I’d chosen the start-up and that if it she was in my shoes she wouldn’t have needed 2 days to decide.

She was proud of me. I can’t tell you how much those words meant to me. In that moment, they might’ve meant more than any “I love you” I’d ever heard.

So now, standing in our kitchen I was worried that I’d be disappointing her if I chose to stay at MD Anderson. I talked to her about the conversations I’d had with myself in the dark (actually, it’s not that dark in our bedroom; we need curtains).

She tried to remain calm and patient, but I knew she was growing tired and frustrated of the back and forth. The decision had consumed our lives. It had filled up every inch of our apartment and it was suffocating us.

“I only have two things to say,” she said.

I’m going to make her late to work, I thought.

“I don’t care what you decide to do,” she said. “But whatever you decide I’m not going to listen to you come home complaining about MD Anderson anymore and IF these guys all become millionaires in 2-3 years, I’m also not going to listen to you whine that it could’ve been you.”

She was right. And it was fair to say. In fact, I loved her more for saying it, but that comfort and relief I’d finally felt last night seemed to be speaking louder. I was going to call the start-up and tell them that as much as I wanted to be their guy, they deserved someone better. My wife told me she loved me and went to work late and without her Starbucks.

About a half hour later I called her back and asked her if it was okay if I changed my mind (again) and went to work for the start-up. She just laughed. What could she say at that point?

“We’re in this together,” she said. “Go for it.”

I signed on the dotted line and gave my two weeks notice to MD Anderson the following day.

I spent the next two weeks working my ass off to leave MD Anderson (and my position) in the best standing possible, saying my goodbyes and not necessarily feeling a whole lot of relief. I downright refused a going away happy hour for fear that the tears I’d shed (every day, I think) would turn into full blown ugly crying in front of my colleagues.

The decision was easily the most grueling I’ve ever had to make. It was uncomfortable, agonizing, panic-attack inducing and bittersweet as hell. (Apologies to those who have to make harder ones, like whether or not to take a loved one off of life support. The intent is not to be self-indulgent or insensitive to the fact that there are *much* harder decisions than whether or not I should stay at a great job or take a shot at a great opportunity; this was simply the most difficult decision I’ve had to make thus far in my life).

“You win either way,” my wife said. (See: if you can’t tell, she’s really smart).


You’ve experienced the commentary now, but how did I actually get to the final decision? After all, that’s what would help you should you encounter a big decision in your own career and/or life.

So here goes:

1.) Leverage Jeff Bezos’ Regret Minimization Framework

The gist is a paradigm to explore big decisions. If I project myself forward to age 80, will I regret not taking this shot? The easy thing to do was to stay at MD Anderson, but I kept thinking back to a podcast I listened to and Brené Brown’s words, “You don’t want to be at the end of your life asking yourself, ‘What would’ve happened had I shown up.” It’s easy to make a life and a career out of sitting in the bleachers, but how would I feel if one year later I was still in the exact same role, doing the exact same work at MD Anderson?

It’s not that there’s anything inherently wrong with that, but I have an insatiable desire to keep growing the breadth and the depth of my skill set. I’m the most engaged when I’m constantly challenged and at a start-up where I’ll wear a ton of hats, they’ll be a big learning curve. I don’t have a choice. I have to learn and I have to do it very quickly. I thrive in that environment.

2.) Ask Yourself, “What’s the worst that could happen?” And can I survive that?

The worst that could happen is that we don’t become profitable, we run out of money, we don’t get more funding and we don’t succeed. Could I survive that? Absolutely.

As one old co-worker told me, “You have to take this chance now why you’re DINK.”

“DINK?” I asked.

“Double income, no kids.”

It’s true. My wife has a good job that she enjoys and my insane frugality provides a really long runway for me to take smart risks before we start a family. Once that happens, our risk tolerance will go down significantly.

Besides,  if I go about this the right way and learn ton (which I should), even if it all falls apart, I should be more employable to other organizations, not less.

3.) Talk to a Ton of Different People.

This started with my wife, my family and my friends. Sometimes this group of people will have trouble giving you objective advice or might be hesitant to offer guidance because they just want to see you happy — and don’t want you to be able to point the finger at them if you’re not. I was fortunate to get great advice from this group, especially my wife who was (and is) a saint for being such an amazing and supportive sounding board.

That said, you have to go beyond these people. I started talking to friends and mentors, most of which thought I should take the start-up gig and had sound reasons — many of which I’ve already covered.

Finally, I sought out other people, in different fields and at different stages of their lives, for advice . This is the group where you can receive some very objective advice and get a wide variety of thoughts and opinions that you can then make applicable to your situation. Don’t skip this step.

4.) Face Discomfort

It’s hard to categorize this one and why it makes sense, but I’ve always heard that when you face your fears you grow the most. This theory proved to be true for me, on a much smaller scale, during grad school, which I documented in one of the earliest posts on this blog entitled, “Be Willing to Step Outside Your Comfort Zone.”

“I’ve found that the greatest rewards I’ve received in my life have come from jumping at the opportunities to take on things that scare me.” – Ashton Kutcher on his decision to play Steve Jobs

To know that this is true is one thing, but to actively practice it is another beast all together. If you’ll regret not taking a shot and you know you can survive the worst case scenario then your fear is just a wasted emotion holding you back. Don’t let it.

Your biggest failure is the thing you dreamed of contributing but didn’t find the guts to do. – Seth Godin, The Icarus Deception

5.) Stop Caring What Other People Think

This is something I’ve harped on for years and link to often. And yet, it’s one of the hardest things to practice consistently.

Nobody ever leaves MD Anderson I told myself. I must be stupid to even consider it. Hell, Glassdoor named it the 5th best place to work in the country. I get great PTO, benefits, retirement, et al.

But here’s the thing. A lot of people will tell you what you SHOULD or should not do, but you’re the only person who can truly make that decision. And furthermore, you should be asking yourself what makes you say (and feel) “Hell yes.” It’s scary going against the norm, but countless people have changed the world by doing just that.

You can worry about what other people will think: Ryan’s a job-hopper, he was ungrateful, he didn’t realize how good he had it, he’s impatient… whatever.

At the end of the day you have to do what’s best for and makes the most sense for you and your family. If this post is any indication, I weighed that decision with great care. It doesn’t do me (or you) any good to waste a lot of mind space on what other people people think. Except, of course, the opinions I solicited as part of number three.

People will always have an opinion, but I encourage you to remember that it’s not the critic who counts.


I still don’t know if I made the right decision or not, but now over a month later, I think about it less. I eat again and sleep a little better. I still miss my old co-workers (see: friends) at MD Anderson and I miss being inspired by our patients there. I miss our janitor, Mrs. Pam. And I miss my favorite security guard. I miss the comfort I felt there and I definitely miss the paid time off, but I also feel great about where I’m at and what we’re working on. We have the ability to really make a difference in the health and fitness community and the self-satisfaction I’ll get knowing that I gave it my all and helped move that needle… well you can’t really put a price on that. Regardless of what happens, I’m (finally) proud of myself for taking a shot.


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  • Fantastic post, Ryan. And what I took away actually wasn’t about how to choose between a new job and a current one, but rather how important a partner can be in tough decisions. Your wife, by the way, sounds genius and you clearly chose well. Her comments through your decision process were honest, supportive, and insightful. Jobs come and go, but (ideally, hopefully) our partner is there throughout.

    I think you made the right choice and appreciate you letting us in on the process. Godspeed in all your endeavors.


    Ryan Stephens Reply:

    Sam – Thanks for the truly awesome feedback on the post! You hit the nail on the head with respect to my wife. She was such a Godsend throughout the entire process. As I wrote the post, I felt her role in the process shining through, but I didn’t necessarily think about it (much) when I actually wrote the post. So thank you for clarifying that, putting it into perspective and bringing her support to the forefront.

    On frustrating days when I can’t seem to move the needle, or I get discouraged, I just tell myself that everything will be okay because I have her in my corner. Knowing I have her support, regardless of what happens with this risk, is an invaluable feeling that I’m grateful for every day.