#3: Tara O’Brien – Organizational Coaching, Leadership Coaching, The Boomtown Startup Accelerator, and Executive Coaching

Sasha Raskin:  Hi, everyone. So this is Go New. I’m Sasha Raskin. And this is a podcast and a vlog and a platform for transformation education. Our goal with that is to help anyone basically to transform their lives, lifestyle, for the better, whether it’s your personal relationship, your career, your relationships with your family, finances, building your own business. Basically all the good stuff that is not being taught in school. It still is not very clear for me why. But I think there is some education transformation that is happening as well.

And I’m very happy to talk to you, Tara, today. So we know each other from working in Boomtown and in a moment I will let you talk about that and introduce yourself. But it’s been such a pleasure working with you and seeing the hard work that you’re doing with helping start-ups to grow something that has a huge potential to benefit others and themselves in a very fast-paced environment. And I think the auto-response email that I get from you every time is kind of a testament to that. 

executive coaching and leadership coaching (business coaching) in Boulder, CO

So take it away, maybe tell us a bit about yourself and the work that you’re doing in Boomtown. 

Tara O’Brien:  Sure. Well, this is my second cohort with Boomtown. And Boomtown runs two, we call them cohorts, two cohorts a year. It’s basically just a very, very intense three-month program that we bring in anywhere from 10 to 12 teams. And when I say teams we could … we usually see two founders come in starting a company either from the idea stage or maybe they are earning revenue already, maybe they’ve been working together for a long time or only just a few months, all the way up to teams that have five or six people and a full staff that have exited companies in the past. So it’s a wide range of human dynamics and group and team dynamics going on. 

And I’ve been … This is my second cohort with Boomtown, I’m the education director here, so really what I’m doing is kind of my main job is to build and facilitate an ever adapting curriculum, whether it’s learning how to handle conflict and team dynamics all the way to building a financial model and learning how to do marketing and branding for their companies or pitching in front of investors. And that program is ever adapting, so depending on the teams that we have and where they need help we’ll kind of adapt that as well as adapt to the human side of our founders as well. 

Sasha Raskin:  Yeah. And what’s your background a little bit?

Tara O’Brien:  Sure. My background is I spent 12 years kind of traipsing all over the world as a journalist, and I did that for about six years and then I really learned that even though I love journalism I love team dynamics even more. And so I started running a television news station and really training and teaching and educating new journalists that were joining the realm of our television station. 

And that’s where I learned after a little over a decade of doing that I realized that I loved storytelling, I loved the way people come together and use their story with others, but I love teaching and educating. I think in the world of education you said there’s a lot of things that aren’t quite taught in school, but it’s starting to emerge, we see it in businesses today – there’s so much in the world of education that is dealing with each individual person to get through to them in the best way possible so they can learn in their own dynamic style, that I just find fascinating.

So I’ve been doing a lot of consulting for the last decade with small companies, doing a lot of coaching and mentoring, and then I knew that I wanted to make my way into the accelerator start-up world and that’s how I ended up here in Colorado with Boomtown. 

Sasha Raskin:  So you did a lot. 

Tara O’Brien:  It’s been a very unique kind of journey from point A to point B I suppose. 

Sasha Raskin:  Yeah. I’m very excited about our conversation today because it’s not really just about business or starting a company or working with a team, I think what you are doing at Boomtown is doing the same thing that everyone does in their own lives every day, but maybe on a much faster schedule and when sometimes maybe there is more at stake. And some of those things are goal-setting and time management, working with others, managing conflicts, being clear on my needs and what I wanted, what the team wants. And I’d love to hear from you about those things. 

My first question is what do you think is the main thing that might stop let’s say all individual to reach their goal? 

Tara O’Brien:  Well, I think it’s an art form to really be able to … you can teach people things in a very accelerated way, which we do here, you learn how to build a financial model even if you don’t know finances very quickly. But I think there’s an art form to learning how each individual person brings their best self forward. And that’s not always, like you said, it’s not always just around the company or the business, but when you really put stress on people and you really push them when they’re not getting a lot of sleep and they’ve got a lot of pressure and they’ve got pressure from their friends and their family, and they’re running out of money, and they’re building this company, and their heart and soul is tied to their success or failure – You can really get to the heart of who a person is.

And I think they become very vulnerable and they become very open. And at that moment it’s critical to be able to figure out how to help that person at their rawest, most vulnerable moment become their best self in all facets of their life. 

And it’s not just in building the company, so as you said, we see a lot of teaching them how to handle conflict and be resilient and communicate better. And we even go so far as to help them learn how to become vulnerable. I think these are the key aspects to helping a founder be prepared in a very well-rounded, holistic way, because if we’re not focusing on the person holistically they’re not going to be able to build a long-term sustainable company anyway. And they’re going to melt down in the process and we don’t want that to happen. 

Sasha Raskin:  Yeah, so people behave differently when there is a lot of stress.

Tara O’Brien:  Absolutely. 

Sasha Raskin:  Yeah. How do you know when stress is beneficial and when stress is not? 

Tara O’Brien:  It’s taken me years and years of learning how, I think mainly through … I did a lot of reporting after the wars happened in 2001 and 2003. So I know what it’s like to be kind of out on the front lines. As a person that didn’t have that background a lot of stress happening around you, people, atmospheres. And I took that, and also I kind of put alongside of that stress public speaking because that’s very stressful as well, so it took me many years to realize for myself that you can turn anxiety and fear and nervousness into excitement and energy. 

Sasha Raskin:  That’s so interesting. I’ll pause you for a moment, because we actually have a video class about brain chemistry, it’s called Turn Your Anxiety into a Superpower.

Tara O’Brien:  Yes, I love it. 

Sasha Raskin:  It’s this energy of being alive and being prepared to take a massive action in the world, right? And the question is can you ride this energy or do you let this energy ride you, right? 

Tara O’Brien:  Absolutely. And I think there’s so much science and research now that’s really starting to emerge in the local media about the neuroscience of rebuilding your brain pathways. If you usually tend to let stress make you feel freaked out and anxious, it’s how can you read refocus that pathway in your brain to actually get excited about it instead? And so this fascinates me personally.

Boomtown is very, very big on founder wellness, so I think they go hand-in-hand. And I can sense just from my life experiences of being around thousands and thousands of people and having to understand their mental attitude at the time, I can sense when people are starting to go down that negative pathway with stress. And that then excites me and challenges me to find a way to re-shift and reframe what’s going on that day to get people motivated and excited, rather than stressed out, burned out.

So we do a lot of here … we do a lot of team activities, we bring in actual coaches and therapists to work with them individually. We have a brilliant young entrepreneur that comes in to teach the brain chemistry behind meditation, and we do meditation seminars. So I think there’s a lot of different things to at least get these founders started thinking in a different way. This is not all about caffeine and no sleep and just go, go, go toward your business. I think we’re starting to see a little bit of a shift in the entrepreneurial realm finally to start taking better care of ourselves. 

Sasha Raskin:  Yeah. And it’s been so interesting for me also to work with you guys as a leadership coach, and the realization that happens in pretty much at the beginning that we’re not going to talk mainly about business, we are going to talk about how you as a person can actually be resourced and resilient in anything that you’re going to do, right? 

Tara O’Brien:  Right. 

Sasha Raskin:  And relationships with others are a part of it. And this is such a hero’s journey, especially for the leaders, right? And I worked with leaders who cannot call themselves CEOs even if they are. Just literally they cannot pronounce it. So it’s like you would think that people in leadership positions are extremely self-confident, and it’s amazing to see that it’s not always the case. 

Tara O’Brien:  That’s very true. And I have to put a little plug for you right now, Sasha. We love having you come in and we love this part of our program, because like I said everyone loves the concept of the holistic approach to founder wellness. And it’s literally one of the most amazing things that we hear from our founders after they leave the program is, “Can I get my leadership coach back?” That was one of the best things that we had during the program, so much value to being able to step outside of the business like you said. And really just be able to be human and talk about behind closed doors in a confidential way what’s really going on aside from the business. 

Sasha Raskin:  Yeah. So you talked … I really appreciate this, and I appreciate being a part of it, and it sounds like this is a part of prevention in a way, right? Prevention. Being overwhelmed with stress and creating and life balance that’s not going to make it sustainable, right? It doesn’t really matter how successful your business is if you burnt out after a year, it’s just not going to go anywhere, right? 

And I think this is the biggest difference between Western and Eastern society in terms of medicine specifically – prevention versus fixing the problem after the problem happens. 

Tara O’Brien:  Right. 

Sasha Raskin:  And what did you do when in terms of fixing the problem? When you see that a person went over that threshold of they’re not in a good place in terms of dealing with what needs to happen and what they need to achieve, what do you do then?

Tara O’Brien:  My personal take and something that I take a lot of pride in and have for many years, I had a handful of amazing mentors that really taught me the value of honest feedback. I think that this is not an easy thing, especially in the entrepreneurial world, I also come from a background other than consulting, of venture capital and dealing with entrepreneurs that were being funded millions of dollars. And it’s just not always an ecosystem where really strong honest feedback is out there. 

And I find that when you’ve got a problem that’s already created and now you’re having to fix it, honest feedback is the only way that that’s going to happen. And the person giving the feedback really needs to realize that your goal is to be honest and forthcoming with what this person … where this person’s at and what they might need. But it’s also to help them be their best self. 

So this is the time that we bring honest feedback, I’ve had many people sitting across from me crying, as they get the honest feedback. But then there’s got to be the ability to lift them back up with actual action steps of how to fix this problem if we’re already in that realm. And so I think bringing in the right people for them to talk to, I think trying to get them to see the value of slowing down, being around family, taking a day off, recharging, regrouping – This works 70% of the time. 

Sasha Raskin:  Yeah. 

Tara O’Brien:  It definitely is not a 100% fix. I mean, especially in the entrepreneurial world there are many people that say, “I just don’t have time to eat. I just don’t have time to relax.” 

Sasha Raskin:  That’s very true. And this is usually my biggest surprise when I start walking with a team, realizing that you have a structure in place for giving each other feedback. They just go and do their own thing, many times in their own rooms, maybe sending some emails to each other, but kind of just isolating each other and there is no information flow, right? There is kind of this wall – I’m doing my thing, you’re doing your thing.

So this is valuable I believe, daily feedback, literally taking that time, 10 minutes, of sharing what works and what doesn’t work. Instead of letting it pile up and then after a month there’s just like a big blowup that comes out of nowhere, right? Instead of knowing exactly what’s happening with me and you when we work together.

Tara O’Brien:  Absolutely. I mean, it’s the same concept of doing maintenance on your house, doing maintenance on your car. If you take out the one hour a quarter to do what you need to do, it really makes a difference. And if you don’t, you’re really going to pay the price at the end. And this is really dealing with people rather than things and machines. And I unfortunately have seen stress get to the point where it will really break people all the way down, it’ll ruin relationships, it will ruin co-founder relationships, family relationships. 

And that’s why I really bring in … not everybody thinks about this, I think it’s important in the beginning when you’re working with entrepreneurs like this, we like to bring people in to talk about these difficult situations, to talk about how taking one hour out of your day to go for a walk and then come back and have the hard conversation with your team will save you a month of pain. 

Sasha Raskin:  Yeah.

Tara O’Brien:  So I think it’s done right this can get through to most people and make such a huge impact. 

Sasha Raskin:  Yeah, and hard conversations I believe don’t have to be just suffering, there can be an element of fun. The Goodman’s they did a lot of … 30 years of research about what helps couples work, and I think it’s just a microcosm of what helps relationships work in general. They talked about, “Well, if we want to make relationships stronger we need to do three things, one reduce the conflict then increase the friendship and the closeness of the relationship, and the third thing is increase the amount of friendship during conflict.”

Tara O’Brien:  Oh, that’s a good one. I like that. 

Sasha Raskin:  So I think it’s really about when I’m giving feedback which can result in conflict – what’s my intention? Is my intention to … let’s say we’re working on a team and I feel missed by the other person, am I trying to hit and run and let the person feel hurt because I feel hurt, right? Or am I trying to create a better stronger relationship that will facilitate growth for what we’re doing together?

Tara O’Brien:  Wow. I think I need you to come in here a lot more often and teach that almost on a daily basis. I love that concept. I think stress can easily push that concept out of our minds, that when we’re in conflict how do we make the other person laugh and take it down a notch. But I think that’s a skill that we could learn and teach early on, and then it just becomes even stronger every time they use it – brilliant, I love it. 

Sasha Raskin:  Yeah, and you would think that it might happen more with type-A personalities or maybe with high-paced environments, but I teach counseling classes where we do exactly the same thing and work with group dynamics, and you could count compassionate counselors in a group and put some pressure on them, just structure-wise sitting in a circle for an hour and a half in a large group, which puts a lot of pressure on them. And they’re given the freedom just go at each other, right? 

Tara O’Brien:  Wow. 

Sasha Raskin:  I want to make you feel pain. 

Tara O’Brien:  Wow. 

Sasha Raskin:  Yeah, and I think there is some intention, maybe good intention behind that, it’s just, “Well, I want to communicate what’s happening for me by maybe making you feel how painful it is for me,” right? And does it really work? Or if it works to some extent what is the price that people are paying by habitually communicating the way they have been communicating even if it’s not really beneficial? 

Tara O’Brien:  Right, and I think we just get stuck in those patterns without … You sometimes need a mediator, moderator, an outside person to come in and really show what that’s doing. And that’s where I think people will turn to therapists or coaches which we’ve seen do wonders here at Boomtown for our teams. Because sometimes you need someone to point out the habits that you are doing and the negativity that it’s bringing. 

I think too one of the things in the entrepreneurial world that I’ve seen is people tend to kind of silo themselves and work in the confines of their home or they work from there office with their team, and they don’t really get a lot of interaction from a bigger … when they’re first starting out in their business journey. And what we see here at Boomtown and what we hear from our founders is you bring together a group of 30 people from 12 different companies, and they really become one company for the first time. They have friends, they have people pointing out their flaws, they have people helping them with marketing needs.

And I think this is the one thing I would love to see shifts in the early stage entrepreneurial world, is really having more people work together in a bigger group. Because I think it can fix some of the things that you’re talking about in pointing out what you’re doing right now isn’t working and this is why. But you need others to see that, and then give you feedback on it before you can make that change sometimes. 

Sasha Raskin:  Yeah, it’s this mastermind that happens when people come together. And then in a way there is a presence of something bigger, right? 

Tara O’Brien:  Correct, yeah. 

Sasha Raskin:  [Unclear 23:34] 

Tara O’Brien:  Very much so, yeah. It’s a great thing to see. And then here we only give it to them for about three months so then they’re always sad when it ends. 

Sasha Raskin:  How do you create a buy-in for someone else to be open for feedback? 

Tara O’Brien:  I think one of the easiest ways for me, and this isn’t how I always did it, this is through a lot of trial and error, is have to find a way … You have to find a way to quickly analyze through body language, through non-verbals, through just kind of the way the energy is in the room of giving something that everybody can relate to. And the easiest thing I’ve come to is normalizing uncomfortable feelings. 

So for some reason, and it took me a while to get here, it’s how do you normalize I understand everybody’s probably uncomfortable right now, I understand some of you are angry right now, I understand that some of you are feelings fear right now. It’s saying the words that people especially in the tough entrepreneurial world don’t normally say, “I’m afraid or I’m depressed or I’m alone and feeling lonely today.” It’s putting those words out there to normalize and make it feel okay to be in that world. And that is something I’ve really seen works for the general group is. 

And then talking about it. And once you get people feeling like, “Oh, there are 30 other people that are feeling depressed right now, feeling stressed or having marital problems or having problems parenting. I feel like I will now buy in to anything else you throw my way. Oh, you want to sit down and have a feedback session? Yes, I’m there.” So it’s really having the difficult conversations upfront and getting people to relax around that I think. 

Sasha Raskin:  Yeah, because if I’m not alone in my struggles I can in do more and I have support and I can relate to others.

Tara O’Brien:  Absolutely, and there’s nothing wrong with me. 

Sasha Raskin:  Yeah, it’s normalizing. 

Tara O’Brien:  This is normal, there’s ten other people that feel this way, oh, now I can easily talk about it and be vulnerable. 

Sasha Raskin:  Yeah, this is so interesting. I remember my conversation in a different podcast with David James, and he’s leading space missions, and he is talking about the importance of talking about emotions with space scientists. On paper it’s kind of surprising, but it’s also not, right? 

Tara O’Brien:  Sure. 

Sasha Raskin:  It’s how can we pop up the balloon, this illusion of people are the roles that they are playing in their organizations? No, they’re just people, right? 

Tara O’Brien:  Right. 

Sasha Raskin:  That are doing things.

Tara O’Brien:  Right. Yeah, I think we’re shifting away finally from the mindset of the 1980s and 1990s where strength and power and holding your emotions back and not showing weakness, those were the … that was the importance in business decades ago. Now I think we’re finally starting … I’m seeing a shift in the last just few years, especially around start-up companies and early-stage entrepreneurs, of now really what makes you strong is vulnerable, humbleness, taking care of yourself. Instead of being prideful of I haven’t slept in six days, I haven’t eaten; I haven’t talked to my family. That used to make people look good, now it’s the complete opposite. So I love seeing that shift. About time. 

Sasha Raskin:  So the college of vulnerability, right? 

Tara O’Brien:  Right. 

Sasha Raskin:  Yeah. Instead of being afraid of showing difficulties or challenges.

Tara O’Brien:  That is totally true. 

Sasha Raskin:  Yeah. And the magic of connection that can come out of that.

Tara O’Brien:  Correct. It does. I think it bonds people in a very different way, and I think it’s also setting up more authentic, more genuine partnerships, friendships, kind of coalitions. We see a lot of our founders leave here and they will remain in contact with the people that they went through the cohort with for years, sometimes even hiring them, partnering with them, calling them when they’re having a problem as a CEO or fundraising. And so they’re really starting to lean on each other a little bit more, keeping that idea of the big group together. I like that. 

Sasha Raskin:  Yeah. So pivoting a little bit, how do you measure success in Boomtown? I know that there are a lot of measurable goals and clearly defined goals. And I’m really curious about it, and also maybe personally for yourself, what is success? 

Tara O’Brien:  Well, I’ll start with the Boomtown and what we think makes a successful company or successful people, and we really truly do focus from the minute we start interviewing before the cohort to bringing them into the cohort through the 12 weeks and then beyond as they become alumni, we find that we have been successful and they are successful if they are prepared for whatever is to come when they leave. 

We know in 12 weeks we can’t teach them everything that they would learn in Business School, we know that we can’t necessarily get them funded after 12 weeks of helping them create a company. But what we can do is prepare them, again, I use the word holistically, to leave here and still be successful. Even if they completely change the company that they’re doing and pivot in three different directions – Do they have the support network and resources and the tools and the confidence to do all of the things that are necessary to then go on and be successful? So that’s how we view success from a Boomtown stance, is how prepared our founders are when they leave? 

For myself, personally, that’s a great question. I would say I find or feel that I’m successful if our founders leave here feeling supported and balanced and excited. I think there’s so many moments in an entrepreneur’s journey where they can feel impostor syndrome, which is a real thing, where they can suffer human dynamics problems, whether it’s at home with their family or it’s with their co-founders. 

I think there are so many low points that they can hit and get stuck in, that I feel successful if … and it is normal to hit those valley, but if I can bring them back up and show them, “This is a journey of peaks and valleys.” And it’s all normal, and if you realize that that is just going to happen as you go, can they overcome it when they’re in those valleys? Can they ride through it and overcome it? Leave here excited, leave here feeling I got this. Even though things might go bad in a month I’ll work through it and I’ve got this. I’ve got the tools, the people, the support and the inner strength to help me get through that. That’s how I feel successful at the end of the day or end of three months. 

Sasha Raskin:  Yeah. I completely agree. What is the secret sauce then? What differentiates teams that are succeeding and feel that they are succeeding as well from teams that do not? 

Tara O’Brien:  Wow, it’s going to sound so cliché, but I actually think … 

Sasha Raskin:  Please do not shy away from cliché. I think clichés have true in them.

Tara O’Brien:  Right? They got there for a reason. I think to be a successful entrepreneur you don’t have to have an MBA, you don’t even have to have a college education, I don’t think you have to have the best company idea in the world or a rocket science team behind you. I think you have to be flexible, you have to not beat yourself up, so you have to have some self-love, some self-care and be able to do that, and you have to be mindful. And that’s the cliché is mindfulness. 

And what I actually mean by that is can you step back and allow to evaluate that you might not know it all, that you might need some help in this area, that you might not be the best CEO, you might not be the best leader. And whether that means you need to step aside and let someone else do that job or you need to go out and learn. I think this is the key to a successful entrepreneur – are you able to step back and question yourself, and either step aside and let someone else do it or go learn how to do it better? 

Sasha Raskin:  Yes. 

Tara O’Brien:  I think that’s what makes an entrepreneur successful. All the other stuff can come in a lot of different ways and the team you bring in can help fill in the gaps, but if you are a leader and you’re not able to do that – I think it’s an automatic fail. 

Sasha Raskin:  Yes, so being open to influence.

Tara O’Brien:  Absolutely. 

Sasha Raskin:  And having maybe the humbleness or just the patience to outsource work to others, right? I do not have to control everything, I do not have to do everything myself. The world will continue spinning even if others will do other things that I won’t be doing.

Tara O’Brien:  Right. It’s absolutely true, yep. I think that’s an art that can be taught and learned. So I think if we could … if every entrepreneur could take a class in that and really dedicate themselves to it I think we’d have a lot more success in that world. 

Sasha Raskin:  Yeah. Well, if we talk theory for a moment I’m thinking about cybernetics theory and system theory and the idea of positive feedback loops and negative feedback loops. Positive being there is a system that can be a family or an organization or a school, whatever it is, that the information flow allows external information to come in and influence the system. 

Tara O’Brien:  Oh, yeah. 

Sasha Raskin:  And the system can adapt and grow and change and be flexible. And negative feedback loops just stay the same, the same information flows and things are … that’s the catch-22 situation. When things are being done just because they’ve always been done that way, right? And nothing changes.

Tara O’Brien:  Right. 

Sasha Raskin:  And there’s no reason for things not to change, right? 

Tara O’Brien:  And I think it’s a control, what you’re saying too is very much a control factor. And when you get stressed and you get put into very uncomfortable situations it’s a normal human tendency to fall back on doing things the way it’s always been done, because it gives you a sense of control in a very uncontrollable environment. 

Sasha Raskin:  That’s such a good point, yeah. 

Tara O’Brien:  So I think it’s very … Again, when I see this coming on I think it’s just a matter of calming everyone down and letting them know this is a very normal thing that happens now, let’s try something different. 

Sasha Raskin:  Yeah. There is so much danger in being comfortable.

Tara O’Brien:  That’s so true, right? 

Sasha Raskin:  In life, right? 

Tara O’Brien:  Yeah, in almost all aspects of life I would say for sure. 

Sasha Raskin:  Yeah. I see that a lot when working as a family therapist with families and the way that they try to solve the problem usually is the problem. 

Tara O’Brien:  That’s so true. And you can try to overcorrect a problem, right? 

Sasha Raskin:  Yep.

Tara O’Brien:  And spend way too much time on it which could make it an even bigger problem. 

Sasha Raskin:  Yeah. The kind of illusion that the only reason that I didn’t fix the problem yet is because I did not try enough the same solution.

Tara O’Brien:  Very true. Wow, it’s amazing how you can take that from your practice. And I can see it with people building companies as well. Very similar. It didn’t work the last time I did it this way, let me try it eight more times the exact same way without removing or adjusting. Yeah, very true. 

Sasha Raskin:  Yeah, humans are humans, right? I asked my history teacher once in high school why do they say that history doesn’t change. Objectively why there are repeating patterns in history? And he said it’s so simple, because humans don’t change.

Tara O’Brien:  It’s true. Wow, all the way down to the smallest aspects from history. It is true. And I think this is a key, what you’re saying is such a point to keeping more people in your network, right? You could go from the family that’s siloed in their house and fighting and trying to make fixes and trying the same thing over and over again, and it’s not working, all the way to an entrepreneur, a couple of co-founders building a company – If you’re alone and trying the same things over and over you’re not getting anywhere. 

I love bringing in a bigger network, a bigger community, family to help you kind of see things in a different way and try new things and try it in a different way. And we use our strongest aspect to Boomtown as our mentorship network. We’re so lucky with all the people in Colorado, the Bay Area, New York City, that we use as mentors. And that’s really what we’re trying to do, is create that bigger community so that people can start thinking about things in different ways. 

Sasha Raskin:  Yes. So the value of experimentation and the renewal, right? By allowing other people to step in and … yeah, maybe I can learn from someone else.

Tara O’Brien:  Right. I’m learning from you right now. 

Sasha Raskin:  Oh, I learn from you a lot. Thank you. Sometimes it’s difficult to take in compliments, you know? So I’m just giving myself the opportunity to do so. 

Tara O’Brien:  Well, good for you. 

Sasha Raskin:  Yeah, I co-teach this counseling class with another great teacher, and she’s telling me, “When you get compliments that you can take in, just kind of imagine putting them in a pouch.” 

Tara O’Brien:  I like that idea. 

Sasha Raskin:  Yeah. And when no one’s looking you can just take a peek and take … Yeah. 

Tara O’Brien:  I love it. 

Sasha Raskin:  And that’s what I love about family therapy and coaching as an extension of “traditional talk therapy” versus letting the client lead the conversation and we’ll just talk about anything that comes to mind, and then I can just hear the same narrative just repeated, right? I’m not afraid to go into the system, organization, or family, or a couple, or the individual and disrupt habitual ways of being in a conversation, right? And it sounds like in the way you’re doing the same thing. 

Tara O’Brien:  It is, because … well, I mean, when you’re dealing with people and especially the emotions that can come with that and the fears and when those emotions and fears can really affect their nine-to-five performance, you have to be able to pivot with them like in the way that you’re saying you’re going with them in their conversation and letting them kind of steer where they need to steer. And then you’re adding in … I mean, you have to be on your game to be able to follow them and help them along the way, instead of you steering the conversation. 

I think that sometimes it is a mistake in the world of education, we do try to steer teaching, even in elementary school education we try everyone the same way and if they don’t fit that mold we say that they need to go get special education or they need to leave the school or they need to go to a special school. And I think this is luckily starting to change but not fast enough. And I try as hard as I can to bring this into my profession, because I living all over the world everybody is different and they handle everything differently. And if you want them to succeed you want them to leave your one hour therapy session or you want them to leave at the end of the day still wanting to build a company, you need to be able to give them what they need along that journey. So it’s not always easy. 

Sasha Raskin:  Easier said than done, right? 

Tara O’Brien:  Right. 

Sasha Raskin:  How do you work with time management? When I hear about the schedules that you create for the start-ups that you help, even listening to it it’s overwhelming sometimes. They just have one thing after another, and while learning stuff they need to produce results as well. What creates a success in that regard? 

Tara O’Brien:  Again, adaptability, flexibility, things … You can set up an entire week full of programming and accomplishments and deliverables and key metrics and objectives to hit for the week, but you’ve got to be able to adjust as you go. But I think too it’s learning how, notice how, how – keyword, how to say no and when to say no. And this has always been difficult for me in my past because I love taking on everything, it’s a great challenge. But I’ve also had a lot of amazing feedback in the past that says, “When you take on 20 things you’re only good at two.” And I don’t like that idea, I want to be good at everything I’m taking on, and so if everything I’m taking on should only be two things and then I can really be good at those two things, that’s the shift I’ve made in the last decade or so. 

And I like kind of helping other people understand that, because in the entrepreneur world you really do think it’s very normal to think I’m not successful unless I’m working a hundred hours this week. And I won’t have time to take a 20-minute walk and get fresh air, I don’t have time. And I think it is you always have the time. You need to learn what else is not so important. 

Learning to say no is one way to manage time, the other way is taking care of yourself. If you don’t get a 20-minute walk you’re really not going to be so productive for the next three hours that you’re going to be working anyway. If you don’t get seven or eight hours of sleep at night, tomorrow is really not going to be that productive anyway. So I think there’s a lot of value to taking care of yourself in order to be productive with your time management throughout the week. 

Sasha Raskin:  Yeah. So the art of adapting to when things don’t go according to plan, and can I say no, or just when things are not going my way just be okay with it, instead of hitting my head against the wall, no, I’m just going to push through. 

Tara O’Brien:  It’s such a good point that you bring up there actually. It’s learning how to accept your failures and think of the word failure in a new light. Failure not being a negative word, right? I didn’t get that done today, I didn’t do well, I pitched in front of a hundred people and it was terrible. Not wasting the time, effort, and energy with negative self-talk. 

Sasha Raskin:  Yeah. Failure is just such a ridiculous human construct. That just leads to negative self-talk or creating negative feedback for others, which is just this is a situation where what I wanted to achieve maybe I didn’t in the way that I wanted, right? There is literally … I don’t think it’s possible when someone tries to do something that nothing was achieved, like there’s literally at least learning happened. 

Tara O’Brien:  Right. And I mean, something is happening, even if you accidently fall asleep at your desk for two hours right in the middle of a big deadline, there’s still something positive to come from that. You wake up and you’re more productive than you would have been for the next hour or you got the sleep that you really needed. That’s such a low level example.

But I think I see in this world, I see a lot of negative self-talk, and I also see the detriment. It can ruin people for a week or a month, and the productivity they could have had if they just would have said, “You know what? It’s okay. I didn’t do so great yesterday. I didn’t meet that deadline. I didn’t build my product to my liking. But that’s okay. There’s tomorrow and the next day and the next day.” So when I see this happen I really do try to find a way to help people learn that failure is not this bad thing that we’ve always been told it is. 

Sasha Raskin:  Yeah. And I think that’s the main thing that stops people from starting projects that might become start-ups or anything that’s bigger than ourselves. And what would be your maybe biggest tip from what you see in terms of self-doubt and taking risks, staring out of comfort zone, for people who are watching or listening and they have a great idea? This could really be a thing maybe it can something creative like writing a book or starting a company or just teaching a new role in their job for themselves, what is your biggest tip that can help them to do so? 

Tara O’Brien:  It’s a great question. I actually just had a conversation not too long ago with my own sister, so very personal to me, where my sister is a brilliant entrepreneur. She has built two companies, one of them failed pretty badly, the other one did fairly well, and now she’s been in a limbo state and we talked recently and she said, “I really want to start these other ideas, but I am frozen with the fear of failure.” Frozen. 

Sasha Raskin:  That’s the result, right? I’m not going right, I’m not going left, I’m not going straight, I just am not taking action.

Tara O’Brien:  I’m not taking action. But I think my biggest piece of advice which is what I give her and what I tell people here is just make little steps in one direction. It doesn’t matter if you go out and start a company tomorrow. It doesn’t matter if you go out and accomplish this in a month. Just leave the house and go do this today toward your goal. Anything. It can be so minor. Go out and talk to somebody, if you’re thinking about starting a business in flowers, go to a flower shop once a week, go to a flower shop, go talk to a florist. Just keep moving in that direction of interest. And at least you’re moving, you’re not stuck. 

I think the biggest piece of advice is don’t sit and do nothing, do something, even if it’s not deliberately moving you in the direction of starting a company. 

Sasha Raskin:  Yeah. How can someone get unstuck? When I start working with clients they usually either having a very negative dip or they feel stuck, nothing is happening and they cannot move forward. And they might have small steps in mind, right? They might be thinking, “Well, how about I just go and talk to a florist,” but they don’t.

Tara O’Brien:  That’s a great point. 

Sasha Raskin:  How can they move forward? 

Tara O’Brien:  So wow, I have … and I’ve even done it for myself, sometimes it’s hard for me to find, I preach to the people here building in self-wellness or personal wellness time, and then I find myself not doing it sometimes for myself. So I actually put it out, usually one month out, I will put these placeholders to go do these things that I find hard to do – I will put them in my calendar. And I really have made a point to hold myself accountable to canceling calendar dates. So if I cancel a coffee with a friend because I don’t have time or I cancel going to talk to a florist when I scheduled it for Wednesday at 2:00, those are the things I hold myself accountable to. 

And after time you may fail once or twice a year or three times or four times, that’s fine. But the key is to get to a point where most of those calendar dates you are actually going to. And that is moving forward. 

Sometimes you might even go as far as to say, “I really need to get out and talk to this florist. I’ve cancelled the appointment 80 times.” Call your friend and say, “Will you go do this florist thing with me? And will you hold me accountable to go?” Reach out for somebody else to drag you. It’s that dragging you to the gym or dragging you out to go take care of something. 

Sasha Raskin:  Yes.

Tara O’Brien:  Get support from somebody else to bring you out and do it. Because once you get over that first hurdle every other one is so much easy. 

Sasha Raskin:  I truly believe in everything you just said. And I feel …

Tara O’Brien:  Well, that’s kind. Thanks. 

Sasha Raskin:  Yes. And thank you for saying that that works for you. And that works for me too, I think when mentoring or executive coaching, whatever it might be, it’s I should practice what I preach. And if it works for me there is a big chance that it works for someone else. 

And I think that calendars are a modern-day magic, right? This is the first action when putting a thought into a reality, right? And I’m actually doing a training right now that I would encourage anyone to sign up for about working with the calendar in a realistic way and actually making things happen. And you said it – it’s all about commitment. And it’s about accountability to yourself and in a way a calendar is a representation of that friend that you’re committed to, right? You can develop a relationship with a calendar.

Tara O’Brien:  You can. 

Sasha Raskin:  Like a relationship of commitment to someone that’s external, like something.

Tara O’Brien:  Very true. Yeah, no, I love that concept. And I’ll go one extra step further and say, “Put a reward on your calendar,” after you’re doing the thing that you kind of don’t want to do. Like, if your reward is treating yourself to a really nice dinner or your reward is going to get a massage or go for a hike, literally put that right after going to see the florist, and you’re not allowed to go do it until you do the things you’re supposed to do. 

Sasha Raskin:  Yes, so the calendar is not just for the boring stuff.

Tara O’Brien:  Yeah, right, no. Well, of course not, that’d be terrible. 

Sasha Raskin:  Yeah. Well, it was such a pleasure and privilege to talk to you today.

Tara O’Brien:  You as well. Thanks for inviting me on. I appreciate it. 

Sasha Raskin:  Me too.

Tara O’Brien:  Always great to learn from you. I can’t wait to see you next time. 

Sasha Raskin:  Yes, thank you.

About the Author Sasha Raskin

Sasha Raskin, MA, is an  international #1 bestselling co-author , the founder and CEO of  Go New , a transformational education program, a  life coach, and business coach and a  psychotherapist in Boulder, CO. He is working on a P.h.D in Counseling Education and Supervision and is an adjunct faculty at the Contemplative Counseling master’s program at Naropa University, from which he also graduated. Sasha has been in the mental health field for more than 10 years, worked with youth at risk, recovery, mental health hospitals, and coached individuals, couples, families, startups, and groups. He has created mindfulness stress reduction and music therapy programs within different organizations. Whether it’s in person or via phone/video calls, whether as  a counselor , a  life coach or a  business coach, Sasha uses cutting-edge, research-based techniques to help his clients around the world to thrive.   As a  coach Sasha Raskin provides individual and group  coaching in Boulder, Colorado, and worldwide via video and phone calls, drawing from over ten years of experience. His services include:  life coaching,  business coaching,  career coaching,  ADD / ADHD coaching,  leadership coaching, and  executive coaching. Schedule your free 20-minute  coaching phone consultation with Sasha Raskin As a  counselor in Boulder, CO, Sasha provides  individual counseling in Boulder, CO ,  family therapy in Boulder, CO, and  couples therapy in Boulder,  marriage counseling in Boulder, and  couples intensives /  couples retreats, drawing from over ten years of clinical experience.  Schedule your free 20-minute  psychotherapy phone consultation with Sasha Raskin

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