5 Steps to Stop the “What If” Treadmill

Quick note: Be sure to head over to the Brazen Careerist’s Blog (Brazen Life) this afternoon, where I share 4 Ways to Get Pumped About Your Current Job.

The act of starting is the key to success that many of us never reach because we are still on a treadmill loop of the What Ifs. For each decision, there are several different outcomes, barriers, potential domino effects, and so on. And if you’re anything like me, you hesitate to make a decision until you have thought of every single What If, a thousand times over.

It becomes your new internal soundtrack. You can’t concentrate on anything else.

Your brain is stuck on examining all of the reasons why you absolutely cannot move forward in a specific direction: you’re not going to get paid enough, you don’t have enough experience, you’re too young, you have a family to support, you’ve never lived away from your parents before, how could you waste so much money or so much time.

Pretty soon, one small What If, turns into a huge story you tell yourself – all swirling around in your head, gaining steam and traction, until you are certain that you original idea was so ridiculous, that you were crazy to think it in the first place.

Being the over-analyzer that I am, this What If treadmill used to be my friend (and probably the only treadmill I’d ever hop on). It used to keep me comfortable, it used to keep me on the safe path, and it refused to let me DO anything that had any value to me.

And even more than holding me back from starting or doing, it was also insulating me from who I truly am. I couldn’t possibly quit my job, or move across the country, or get a cat, or buy a new car, or go back to school, or so on – only after getting off that mental treadmill, was I able to see how much I was holding myself back – wishing that I had taken many steps so much sooner.

5 Steps to Get off the What If Treadmill

1. Get all of your What Ifs out of your head.

I know, genius, right? But stop giving your What Ifs power by letting them grow and fester in your mind. WRITE THEM DOWN. Stop living in your head.

Be fully transparent with yourself, you do not have to share your What Ifs with anyone, but write down in one setting, each and every potential road block along with all of the intricacies.

Do not stop at only the “why I can’t do this,” but also capture “the because” that follows. This step alone will help you feel lighter, and less pressured – I promise. If you still feel as though you’re stuck in a specific decision cycle, continue to the next step.

2. Reality-check your treadmill.

Seeing your various options written down on paper in front of you, cross out the ones that feel ridiculous – sometimes our minds get away from the reality of the situation, and seeing it written can seem like it’s laughable or even implausible. Cross the What Ifs that make no sense to you on paper, and if they all make sense, at least you have thoroughly reviewed your options.

3. Worst case scenario it.

In college, my roommate gave me the Worst Case Scenario book and it made me realize that sometimes the worst thing that could happen isn’t all that bad after all. Go back and review your remaining list and figure out what is the absolute worst thing that could happen for each If. Think each scenario all the way through and be sure to capture it on your index card or paper.

4. Let it breathe.

You do not have to make a decision right.this.moment for most decisions. If this is a situation that you’ve been pondering for enough time to let it hop on the treadmill to begin with, I’m guessing it’s not an urgent life or death situation.

So let your What Ifs and the scenarios, breathe. Look at them, revisit them a few times, and continue to see which ones resonate and which ones can be crossed off the list. Some are just not practical, and others may seem too aggressive. That’s ok – just sit with them for at least 24 hours, and let each If breathe.

5. Give yourself a deadline.

Pick a date in the near future that you will make the decision by – pick one that feels comfortable to you, and subtract one day. Make a commitment to yourself that you will have a decision of how to move forward by that date, period. If you need someone to help hold you accountable to that decision date, let me know – I’d be happy to help you out with that.

Follow Your Dreams – You’re Never Too Old… Or Too Young

Bold acrylic necklaceI just spent an amazing weekend in New York for the Make Sh*t Happen Weekend of Genius, and I am so energized and inspired by the others who attended. While I learned MANY things from them (and there is more to follow about the experience), I kept thinking that you are never too old… or too young, to start.

Until this weekend, I was usually the youngest person in the room trying to prove my experience and credibility to an older crowd: “listen to me, I know what I’m talking about;” “I have a new perspective, I’m not being juvenile;” “I have the pulse on the market you’re trying to target – listen to me!” But the tables finally turned on me, and I experienced feeling too old or too experienced to blaze a new path. My peers in the room were much younger than me and having the same thoughts, concerns and questions: “am I on the right path?;” “is it too soon to follow my dreams;” “will people take me seriously?”

You are Never Too Old or Too Young to Follow Your Dreams – BE BOLD

Following your dreams is not about age, it’s about being bold enough to put your thoughts into action. When in doubt, remember to BE BOLD!


  • Being brave enough to question your path and follow your dreams, does not follow a specific timeline. Asking difficult questions and being strong enough and give words and action to your inner most desires and dreams, allows you to plant the seeds to follow any career dream.


  • You do not have to have 10 years of corporate experience before you are considered an expert. You do not need to be a recent grad or a millennial, to go after a career that fulfills you. Expertise does not come with age – in either direction, it comes with knowledge, skills, hard work, and the drive to make yourself into an expert in something that you enjoy.


  • Believing in yourself and your dreams is the single most important step in the journey. If you do not believe that you are capable of your wild path, then why would anyone else? Great leaps in our society have always come from people whose ideas were doubted and ridiculed – but they believed in their idea and never gave up. You are not silly/crazy/ridiculous/unrealistic for wanting something different – believe in YOU, even if it feels like no one else does. You are not alone in your desire to change, and your belief in yourself will help you find others on the same journey.

Own it:

  • No more excuses – eliminate all of your excuses. Never again fall back on that crutch of your excuses: being too old; being too young; having a family (or not having one); starting over; not having enough/too much experience; not enough money saved up; not knowing where to start. Own your dream, just like you would any other object. You have to put gas in your car and water your plants for both to work – treat your dream like something that needs to be nurtured, and do not let excuses get in your way – keep watering it.


  • Learn everything you possibly can about your dream and then learn some more. Objections are more easily assuaged when we have facts to negate them. Learn about the facets of your dream, learn who the key players are and connect with them for advice, learn about the many paths to fulfillment, learn the skills needed to do your dream job. Turn your inner naysayer into a supporter through knowledge – and then apply your knowledge as part of your differentiation package.


  • Never give up on your dream. I’m not going to lie to you – it’s hard to stay on track and keep at it when you are going against the “normal” path. Following your dream takes all of the things above, but without determination and perseverance, your dream will never turn into reality. This is the action step – this is the differentiator between people who are dreamers versus people who are doers. You don’t have to be the best, the smartest, the youngest, the oldest, the most creative – you have to be the most determined. You have to continue to focus on your dream and not lose sight that your dream is worth pursuing; your personal path is meant to have some bumps – or you wouldn’t appreciate it as much once you arrive.

Photo Credit: By sakocreative

Break Out of Your Comfort Zone and Grow

Remaining comfortable will keep you stuck.

I have found myself in a rut once or twice, particularly when it came to my job. I’m not a huge routine person, I actually don’t mind change, but I inherently feel “lazy” most of the time. Sometimes I don’t push myself hard enough; I’m not as ambitious on the outside as I am inside my head; I don’t like to be outside of my comfort zone. I mean, who does – it’s called COMFORT for a reason. For as long as I can remember, I stayed firmly in my comfort zone… I did what was expected of me, I outwardly cared about things that I was told I should care about, I didn’t do anything that would appear as embarrassing to others. Until I almost had a meltdown at work…

I was traveling about 75% of the time and doing so much for the company (ahem, relocation) and my clients but was not feeling the love in return. One day, I literally had enough – I went home and for some reason, I JUMPED outside of my comfort zone and booked a cruise to Alaska, leaving in two weeks. By myself. Go ahead and gasp out loud, it happens every time I tell someone that. I felt prepared for my seven days of vacation bliss by myself in the middle of the ocean. At the time, I didn’t really question it – if felt as though it was something I could do, within my small zone of comfort since I had traveled on my own before. Until I arrived at my room and it sunk in. I was not going to have contact with anyone I knew, for seven days.

Being Uncomfortable, Brings Results

I was SO uncomfortable – I tend to be a bit shy in typical social settings; I did not know another human being on the ship; it felt like I was the only person traveling on my own; and people were making comments and muttering about it to my face! But I was DETERMINED. It was the first time in ages that I felt energized and engaged. I was uncomfortable as hell, but I turned it into a game – I refused to let others tell me how I “should” be vacationing, or have their judgments influence MY first real vacation. I learned very quickly that being uncomfortable, forces you to start doing something.

When you’re stuck – either on an issue, questioning how to move forward, which answer to go with, what your passion is – whatever it is, you need to start with doing something that nudges you outside of that safety zone. Being uncomfortable provides you with a new and different perspective about… everything. With your new perspective, answers will seem to just appear. But more than simply solving something, you will change your perspective about YOURSELF. I have never been so proud of myself in my life – there may have been a tear or two in my cabin after the first dining room experience, but I finally saw myself as a strong, brave, courageous person. It was the last time I ever cared about what someone else thought of me – truly, I have not cared an iota since; because I saw my own truth shining brighter than their judgments. This one act of being uncomfortable has propelled me on my mission to live the best life FOR ME that is possible.

Here are few of the ways that I’ve pushed myself out of my box I call comfort… not at all inclusive, but I’d love to hear some of the ways you’ve pushed yourself:

  • Attended a speed dating event
  • Plan a weekend trip to a city – along with activities and sightseeing planned
  • Went to a piano bar by myself on a Saturday night while out of town
  • Walking tours – one of my favs was the coffee walking tour in Seattle
  • Comment on your favorite blog
  • Take an exercise class with other people
  • Invite a coworker that I don’t interact with much, out to lunch
  • Go to a movie by yourself – if that feels just too awkward, I found that going on Saturday or Sunday morning during the first showing, is typically less busy
  • Go to a museum – it’s a good way to be around other people while still doing your own thing and taking in amazing scenery
  • Go on a hike with someone who’s more fit than you
  • Attend a networking event (I think I just heard you groan), and make it a goal to speak with five people
  • Go to a community/religious “open house” event – this one still kinda freaks me out
  • Join an adult kickball league (or any sport)
  • With a smile, say good morning to the person in the elevator
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Moving Forward without the End Result in Mind

I am a type A person. It’s a label that has been thrown at me: sometimes to offend or insult me, but usually in acknowledgement of getting things done. It used to be a dirty word to me, or a character flaw, but it is who I am. I’m always pushing, driving, completing, inpatient. It has worked in my favor most of the time, but it has definitely gotten in the way on my path to my dream job.

When I was finally ready to make a choice about my career, I found myself frozen. In my mind I knew exactly what I wanted… not to be in a corporate job, but I had nothing else formulated. I was stuck in analysis paralysis. So instead, I created a web of “if, then” activities to help move me along. My plan looked a bit like this:

  • If I quit my job, then I can start figuring out my business
  • If I figure out my business, then I need to get certified/education
  • If I complete certification, then I need to determine my niche
  • If I determine my niche, then I can write a business plan

I think you see the pattern here. I set myself up for failure while hiding behind stagnation. I absolutely refused to move forward on any task, without completing everything in a linear fashion or having all of the answers lined up and ready to go. I have no clue why I thought that – it’s not how I typically approached the world; it’s definitely not how I approached work-related decisions/actions, but I was uncertain about how to move forward without having all of the minute details of the end result, all laid out with a pretty bow on it.  

I had a million ideas of what I wanted to do. I knew what my skills were. But I literally could not put pen to paper on any other item, until I ticked off the action item prior to it. And I accomplished nothing. People around me wanted to hear what my plan was. What I was going to do? What is my new business? I remember explaining to someone that my plan after quitting was going to be “to plan what I wanted to do.” And I honestly set-out to do that! And I failed.

Starting Something… Somehow

But here’s what I learned. You don’t need to know what the end result looks like – in fact, you may be at a disadvantage if you have everything planned out perfectly. Instead, I just started… in the middle. I thought about who I wanted to interact with; I brainstormed business names; I designed website samples; I created a list of things I love doing. I just started. Each mini-step, and sometimes they were miniscule, brought me closer to figuring out what my dream job was. I did not need to complete things by a checklist and I did not need to know where exactly I was going, it was the act of doing; the momentum of starting; the engagement with thinking; that ignited my broad view of my dream job.  

The end result, once you get there, will always be wildly different and bigger than you ever could imagine – so dare I say, it’s almost impossible to have it ready with a bow, before you take your first step? There will be no then, if you don’t start with ONE if.

My Sister the Fashion Designer

Everything Starts from Your Imagination

shelby simonI was lucky enough to grow up in a family with a lot of kids – as an adult, I feel blessed to be able to look at my four siblings and learn from each of them. We are all very different in so many ways, but we are also from the same house, they are my peeps and often reluctant sounding boards.

My youngest sister has always been the most different from me, almost un-relatable, ok dare I say it – there were times that I thought she could be from a different planet. I am innately so type A and a driver, and she’s always been a creative dreamer. If we’re being honest, I thought she was irresponsible at times, perhaps a bit flighty, and definitely unrealistic. All of the qualities that I had a preconceived notion of, that would prevent success. During my sabbatical from Corporate America, I finally allowed myself to talk to her in-depth about her career and life choices. My sister the fashion designer, changed my life (and she didn’t even know it).

Choosing Your Career When One Hasn’t Chosen You Yet

I was stuck thinking work HAD TO BE a certain way. I had to commute to a building I hated; I had to earn as much money as possible and then ask for even more; I had to interact with people who I ethically clashed with; I had to listen to bosses who had merely sat in a certain seat for a period of time; I had to keep climbing and climbing even though I hated every second of it. It sounds so trite looking back at it, but it was my reality at the time. I HAD to do these things because I was the responsible one. When I called my sister and asked her about fashion, where she was going with it and what was next. I just HAD to know what her five year plan was, how she was going to pay her bills, how she could love her job and act so irresponsibly (in my perspective from afar). She laughed – an honest-to-goodness laugh and then asked me one question: “I don’t understand. If you hate your job, why do you do it everyday?” Yes, I’ve thought that many times before, but what followed was how SHE approached work – it was a non-planned approach really, she just did it (and didn’t see another alternative – she clearly had found her passion).

She had doors slammed in her face, she had to live with roommates, money was tight at times, she had to put up with fussy designers and even fussier clients; but her world didn’t implode around her. She paid her bills, had an amazing social life (I still don’t hold a candle to hers), and lived without regrets about anything. Her approach was SO DIFFERENT than mine, it was almost foreign. Through that one conversation I realized that there are millions of people who don’t follow the “corporate ladder predetermined path” of work and are still very successful. And I don’t mean those people we see on TV or the random one-in-a-million success stories. I know a whole bunch of people who consciously chose their own path and career, without second-guessing if their parents were supportive; what the neighbors would say; how it would look; and so on. They are my baristas at Starbucks who work there to help supplement their music; they are the people so passionate about their job at the Container Store that they stayed on for over 20 years; they are an artist who refuses to give up on his talent; they are MY SISTER – who grew up in the same house as I did, and never once thought about NOT being a fashion designer. What in the world was holding ME back?

From that one conversation, my preconceived notions about my options, my family, my sister, and success, were all turned upside down in the most enlightening way possible. I saw that I had made many choices to get me to that job I had loathed, but I was finally at the place where I was able to  make the choice to get off the treadmill to follow something else. I saw my family was supportive, not indulgent as I had seen it before – if they supported my sister following her dream without question, surely they would be open-minded about mine (more about this in another post!). And my sister the fashion designer, became my INSPIRATION, my biggest silent supporter, and reignited my imagination.

When I’m struggling, I remind myself to be more like her, and I urge you to do the same.

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