Last Updated on March 19, 2026 by Fly High Coaching
Entrepreneurial challenges are something every business owner faces along the way. But many professionals and executives struggle with how to handle them when things get real. You might wonder, am I staying focused? Am I making the right calls when everything feels uncertain?
In this episode, you will find real, practical help for handling entrepreneurial challenges. Our host, Porschia, sits down with returning guest David Shriner-Cahn for a warm conversation about navigating career pivots, staying focused, and building real stability in your business.
They open up about the obstacles that trip so many of us up. Things like shiny object syndrome, where every new idea pulls you in a different direction. Time management struggles that leave you exhausted but not productive. And that tricky question of when to pivot versus when to stay consistent. All these little things can quietly slow your growth.
David Shriner-Cahn is the host of Smashing the Plateau, a platform he built for professionals leaving corporate roles to start their own thing. His work has been recognized by Forbes and Inc. Magazine. But more than that, he truly understands the journey. He helps business owners build stronger foundations through community, accountability, and guidance that actually meet you where you are.
What you’ll learn:
- Why it’s so important to face entrepreneurial challenges head-on if you want your business to last
- The hardest problems that trip people up when leaving corporate careers behind
- How shiny object syndrome quietly steals your focus and makes decision-making harder
- A simple but powerful way to think about time by designing your ideal week
- Why watching your cash flow and planning ahead keeps your business steady through the ups and downs
Resources:
- Episode Transcript
Porschia: [00:00:00] Hello, I’m Portia Parker Griffin, and I wanna welcome you to the Career 1 0 1 Podcast, a place for ambitious professionals and seasoned executives who want an edge in their career. We’re talking about all of the things you were never taught or told when it comes to career growth, development, and change.
Now let’s get into it.
Today we are talking about overcoming entrepreneurship challenges with David Shriner Khan. David Shriner Khan’s weekly advice program has been named by Forbes as a podcast to power up your ultra lean business. David has also been recognized as an entrepreneur that will change the way you communicate by Inc.
Magazine. David is the podcast host and community builder behind Smashing the Plateau, an online platform offering resources, accountability, and [00:01:00] comradery to high performing professionals who are making the leap from the corporate career track. To entrepreneurial business ownership. Smashing the plateau is David’s solution to problems that keep entrepreneurs up at night, as he likes to say, with the help of people just like you in our community, you’ll be able to do more of what you love and get paid what you’re worth.
Hi David, how are you today? I’m
David: great, Portia. How are you? Good to see you.
Porschia: I’m doing well. Great to see you again. I’m excited to have you with us to discuss overcoming entrepreneurship challenges. But for those of you who don’t know, we were fortunate enough to have David on the show a while ago, back in episode 33 when we discussed developing an entrepreneurial mindset.
And I think David, that was one of our best entrepreneurship episodes. So for anyone who wants to know more [00:02:00] about David’s background and his career, please check out that episode.
David: Thank you, Pia.
Porschia: Great. So David, one thing that I don’t think we covered. In a lot of detail back in that episode was some of your own personal career challenges.
So I’m interested to know before starting your business what would you say was your biggest career challenge?
David: I would say that there are two, and honestly, there probably. The bigger kinds of challenges that most people face. One has to do with making transitions, like how do you make a pivot when it is either proactive or reactive?
And the second is what happens in between those pivots. Which has to do with perseverance. And so for me I’ve had a few pivots in my career. Some of them proactive, some of them reactive. The first one [00:03:00] that was a big one happened in my late twenties. I was I had just finished my second year in my second job as an engineer.
My boss called me into his office and this was just, this was a month after I had my performance review. It was a really good review. I got a nice raise. Anyway, he calls me into his office and he says, David, I have good news and bad news. The good news is you’re doing a great job. The bad news is you don’t have a job here anymore.
And I was like, what? I was. Not trained in business. I was trained in engineering. I focused on solving engineering problems. I didn’t really pay a whole lot of attention to the actual business of my employer, which was what paid their bills and paid my salary. They had lost a lot of contracts and it was a consulting firm.
They’ve lost a lot of contracts [00:04:00] and, ended up firing a significant percentage of the staff, of the professional staff, myself included. So I was a bit blindsided by that and took me a while to figure out what I really wanted. To do as my next step. I did a lot of soul searching and some personal development and ended up going into the nonprofit sector.
So I didn’t practice engineering anymore after that. So that was a major pivot. And I’ve had some others along the way. I started my own business in 2006. That was a pivot. But I had, I didn’t change fields. I. When I started my business. So it wasn’t that kind of transition.
It was what my working environment was. And I obviously, I had to utilize skills that I didn’t have before. Like particularly marketing and sales was something I was never involved in, so I had to learn how to do that. But the other piece that is challenging is what happens in between those [00:05:00] pivots, which is for me trying to avoid shiny object syndrome actually takes a lot of work.
And and entrepreneurs in particular I think are subject to this shiny object syndrome. What other people are achieving. Other people give you advice like, oh, you should be on I don’t know. You should be on TikTok. You should have a YouTube channel. You should be you should be mining LinkedIn for leads.
You should be changing your business model. You should be charging more. There are all these things. And then you see other people in your in your sphere, whether they’re direct competitors, indirect competitors, or even other. Entrepreneurs in different kinds of businesses that seem to be achieving the kind of success that you wanna achieve, and they seem to be achieving it faster.
So it’s very tempting to try it. Lots of different things as opposed to just sticking with stuff that seems to be working reasonably well and [00:06:00] just getting better and better at it. I’ll give you an example. I. You mentioned podcasting. You’ve been on my podcast. We’re gonna do another episode soon, and I started podcasting in 2014.
That’s already over a decade ago. We’ve released episodes every single week since we started, since the first week, which is not so easy to do. And. It hasn’t always been clear exactly what the impact is of doing this podcast, and I’m sure you probably have felt this too, as a podcaster. Some episodes are really great.
Some episodes, eh sometimes I. There seems to be a fairly direct correlation between the podcast and your business objectives. Sometimes not so much. So how do you keep doing this sort of week in and week out for all these years? Takes a lot of perseverance. That’s true with a lot of things in our careers, in business.
It’s not always clear why we should keep doing [00:07:00] something. Even if it seems to be working reasonably well, this shiny object syndrome is a big distraction. So being able to focus on the long term and keeping doing work that may not appear to be so sexy is hard to do.
Porschia: You said a lot of great things there, David and I completely agree.
You made me think of a question that I think comes up a lot for entrepreneurs. Yes, the shiny object syndrome is a real thing and it is very difficult to move through. But how would an entrepreneur know if they should stick with something or if they should pivot and do something else?
David: The reality is, I don’t think you really do know Uhhuh.
I think I think you, to a certain extent, you need to trust your gut, right? And our it’s funny, but our intuition tells us [00:08:00] things that we need to pay attention to. So yes you should have metrics for the important. Elements of your business and you should pay attention to those metrics.
Obviously the financial metrics are important. There are other metrics are important and if we’re talking about a service business. Like yours or like mine. We want to have impact on the people, with the people that we serve. There are ways to measure that bes besides just the financial metrics.
And we want to get feedback from our customers and clients to make sure that we’re doing as good a job as we can do. And we wanna find ways to improve, but it is not always clear. When we should do, continue to do something and when we should give it up. And I mentioned the podcast. So for example if when I step back and look at some of the benefits of hosting a podcast for over 10 years, I can lay them out.
It’s an interview [00:09:00] based show. We’ve had a few solo episodes, but they’re almost all interview based shows. So I’ve connected with some great people and I. Relationships are really important in business and in life, that alone to me is of great value. And having a podcast is an easy vehicle to continue to always build relationships.
I can invite new people to come on. I get requests from people all the time that I don’t know who want to be on the show. It’s a great way to, again, to connect with new people, to deepen relationships with. People I already know. That’s, that’s a great thing. Do I know where they’re gonna lead these kinds of relationships?
No. It’s in particular, I don’t view relationships as being particularly transactional. I look at them as being collaborative and sometimes I’m able to help somebody who is in my network. Sometimes I can’t, sometimes people can help me. I. And I really can’t do much for [00:10:00] them, and they’re happy to do it, which is great.
That’s how the world works. So I don’t think we always know when to keep doing something and when to give something up. I wish I had a good answer, but I don’t.
Porschia: No, I think that, it actually was a good answer and you gave us a lot to think about. Especially when it comes to entrepreneurship, because there really aren’t any guarantees, so to speak.
It is about trusting your gut, like you said before. And then I think that just having this conversation, so if somebody had that question about should I stop, doing TikTok for example. Or start doing TikTok. I think that’s also the benefit of working with a coach, right? And also being in a community where, you can get some feedback from other people who might have different perspectives.
And while they might not specifically tell you what to do, that can give you more insight than. You had before. Love it. Love it. So David, you have a very interesting background. We know that you’ve, been in [00:11:00] engineering and also the nonprofit world, but what motivated you to start your business and focus on helping people transition into entrepreneurship?
David: So I wanted to start my business ’cause I wanted more control over my career destiny. It really in addition to the fact. I just, I think I just like having control over my environment. I’m probably not particularly unique when it comes to that, but that first layoff that happened to me that I mentioned that was always in the back of my mind.
And one of the things that I’ve learned over the years is when you have a job and you’re. The income to pay your bills primarily comes from your job. The job is great. It’s it’s very steady. As long as you get paid. The minute the job goes away, your income goes from a hundred percent down to zero.
Then you have a gap. When you get another [00:12:00] job, your income goes from zero back up to a hundred percent the minute you walk into the next job. When you’re an entrepreneur, you you’re unlikely to lose a hundred percent of your income instantly. Particularly if you work to diversify your revenue sources you.
Personally I think there’s less risk and it,
You have it, it, on the other hand, it takes time to build up revenue and stability as an entrepreneur compared to as an employee. So I think, in terms of, in terms of risk and reward? I think entrepreneurship, for me it’s I think it creates greater stability and again, going back to like, why did I do it?
I just wanted more control. And yes, in initially it was scary to have to go out and and generate sales, but once I started to figure out how to do that, it got [00:13:00] easier and easier. Now, the piece about helping entrepreneurs, start, run and grow their own business after they’ve had a long corporate career.
That wasn’t actually something that was on my radar when I started my business at all. That kind of found me, and it happened in, in bits and pieces and has evolved over the last I’ve been in business now for I guess it’s 19 years. Yeah. So that, that has evolved and the more and more.
People who have sought my guidance have had a similar journey to mine, which is they’ve they’ve had some kind of corporate career, and I define corporate as you worked in somebody else’s structure as an employee, whether it’s a, big public corporations private corporations, small business, government, nonprofit whatever it is you’re fitting into somebody else’s structure.
And and most of the people that have sought my guidance have. Gone [00:14:00] from that kind of environment to their own business where they stay in the same discipline that they were in, in corporate. So that’s not a new sort of new learning thing. And they are the primary offering to their clients or customers.
They may have a team usually it’s a modest team, but they’re the face of the business and they’re selling themselves. So they go from a place where. They’ve they’ve had a a full calendar. It’s overflowing inbox team of people to take care of things and it’s built in social structure to an empty calendar, initially empty inbox, no social structure spending all this time alone.
And nowadays, most people like this. Work from home, or especially initially, they’re working from home. So there’s a lot of alone time, and then you have to. Get up every day and do something that you have never had to do before, which is market and sell yourself. That part of the transition is very hard.
[00:15:00] And as I said, those kinds of people have sought out my guidance. And what I have found is super helpful with people like this is to connect them with like-minded entrepreneurs in a facilitated environment. Because, you mentioned it, you get this sort of impartial viewpoint and shared experiences about how to solve the kinds of challenges that we all face.
And that can be super helpful and it shortens the learning curve to get you. Whatever the hurdle is you’re dealing with it’ll help you. And I’ve seen this over and over again. It’ll help you make more money. It’ll help you make money faster. It will help you avoid going down rabbit holes and wasting your time and wasting money.
It’ll help you find resources you might not know existed. That can be super helpful. So there are all kinds of reasons to do it but again, it’s like. That particular niche found me, but I was paying [00:16:00] attention to it. I was open to it. I really love serving the kinds of people we have in our community.
We have in our podcast audience. And I think I honestly the people that I interact with every single day, I think make this world such a better place that it just it’s a reason to get up in the morning.
Porschia: Wow. Love it. Love it. You, I think you started touching on this, but I want to hear more.
Why do you think the ability to overcome entrepreneurial challenges is important?
David: If you wanna be an entrepreneur, first of all, we all face challenges, whether it’s in life, in business, if we’re employed, we face challenges in our work. There are always challenges. If you want to succeed and increase your rate of success as an entrepreneur the only way to do that is to figure out how to overcome your challenges.
So I think it’s critical and it’s like hand in glove with being an [00:17:00] entrepreneur.
Porschia: Agreed. Agreed. Yeah. I tell people that, as an entrepreneur, you are a problem solver. And to your point about waking up in the morning and doing something that you’ve never done before. Yes, there’s the sales, there’s the marketing, and then there’s all of the other fire of the day, right?
Oh, this technology software isn’t working. Now we have to figure out how to do this. We’ve gotta figure out how to do that.
David: And we don’t have big teams to do these things for us.
Porschia: It might just be you starting out. It might be you and your assistant, or you and your small team of contractors or employees.
And yes, to your point, there’s not a whole department for that, right? Like you have when you’re in corporate or you’re working for someone else. So about 25% of our clients are either interested in entrepreneurship. Or already have a business. We talked about mindset in episode 33, but I also see that time management is a major obstacle.
What are your suggestions for entrepreneurs who have [00:18:00] issues with time management?
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David: So I think what you actually need to do, and this is an exercise that we have as part of our SMASH framework. I think what you need to do is we’re all used to goal setting and. I believe that we need.
Audacious goals that are specific enough so we know when we’re working toward them, but they’re not metric driven, so that there’s always more to do. And they, and if you [00:19:00] go through this exercise and draft your goals that way, you will have kind of a guiding light for the rest of your life. And you can, you can re revisit them periodically and tweak them.
But I find that for most people, these big goals don’t change a whole lot over time. So that’s one. So the exercise with regard to time is when also this is a very future oriented exercise. If you look into the future, what would you like your ideal week to look like? In terms of what is your schedule?
Just map it out over seven days. ’cause we’re all used to a seven day cycle. Humans all over the world all follow the same seven day cycle. We don’t, we argue about a lot of things. We don’t argue about the days of the week. We, everybody has agreed to this, right? So map out what you would like every single day to look like in terms of what are the things you’re gonna be doing.
That [00:20:00] are work oriented, what are the things that you would consider I don’t know, personal, cultural, spiritual physical like whatever the major buckets are that are important to you in your life. How do you want your time to be allocated to those various buckets? And then when you look at your immediate calendar.
How does that compare to your ideal week? And look at where the gaps are. You will find when you do this exercise that you will probably be spot on some of the major. Categories that are important to you, and you may be off and sometimes off by quite a bit on some other ones. So what it means in terms of time management is you can’t make more time.
There are 24 hours in a day. There are 168 hours in a week. So what. What it likely means is you have to start saying no to some things. ’cause you can’t [00:21:00] say yes to more. Like we all have gone through this where you create a to-do list and you put 10 items on the to-do list and at the end of the day, if you’re lucky, you finish two.
And all that does is leads to frustration. So if you wanna get better at time management, look at what’s really important to you. Figure out where you are. Where you’re off and what you can say no to. And keep in mind one important thing, which is the 80 20 rule, which applies to, I find it applies to pretty much everything we do in life, in business, et cetera, which is 80% of our success comes for from 20% of our activities.
So when you do this exercise, you can probably stop doing. A lot of things that you’re currently doing, and it’s not gonna have much of an impact on where the, where you’re headed towards those big goals. So just be prepared to let it go. [00:22:00] And if you can do that first, then you can figure out other techniques like there’s, the, oh gosh, I forgot the name of the book. A Alan’s book about time management. He has a system that he uses to e either do it now, defer it. Delegate it. Yeah. Which is a great way to think about things. If you can do something in two minutes or less, do it now. Otherwise delegate it to somebody else or defer it to another time and put it on your calendar.
So there are all these different systems you can use. You could find one, that one happens to work for me. There are a lot of these different systems. You can find one that works for you, but you can’t do more than you can accomplish in 24 hours in a day. And you wanna spend some time sleeping and eating and.
Socializing. So really look at you, look at what’s ideal for you in terms of your ideal week. And then look at what you’re doing now. Identify where you can make some cuts. ’cause you’ve gotta make cuts first. And then figure out, okay, how can [00:23:00] I. Generate more success in the areas where I have some gaps in what I’m trying to achieve.
Again, whether it’s financial, business, personal relationship building cultural, spiritual physical exercise, mental health, et cetera.
Porschia: I love that. I wanted to get your engineering brain on the time management conundrum. David love what you said about, just making those cuts first and thinking about what you can say no to.
And then, utilizing Pareto’s principle, the 80 20 rule I think is also really beneficial. From your perspective, what are some of the biggest problems you’ve seen executives and entrepreneurs have when it comes to overcoming challenges in entrepreneurship?
David: One of the big ones for entrepreneurs and this is true actually for it’s true for employees too is lack of cash.[00:24:00]
This is a very practical thing that you can solve, right? Your income minus expenses equal surplus, and you can build up a reserve. The bigger the reserve you have, the more cushion you have for when stuff happens that you didn’t expect. So if you’re, have a right, if you have a job and you have. Let’s say you have 12 months worth of expenses covered with a reserve, you get laid off.
You’re not gonna have to make any changes in your lifestyle if you don’t find a job in 12 months. Yes, it may feel uncomfortable to spend down your reserve, but I, but keep in mind that’s what it’s there for. And the number one reason for business failure is lack of cash. And I’ve seen this over and over again.
I’ve seen entrepreneurs that have [00:25:00] built up a fair amount of cash and when they feel like they, they need to take a break because they’re feeling a little bit of burnout they do it and they say I’m taking some time. We’re not worried about generating income. I’m gonna take X number of months.
I’ve seen people even do it for a year or two because they can. And then there’s the, all of a sudden the market changes. I. Or we’ve experienced in this country a couple months ago, the political world changed, which impacted a lot of people very quickly. Employees, entrepreneurs, a lot of things have changed very quickly.
And I’ve seen some people in our community have had both ups and downs as a result of these kinds of. Changes that are beyond their control. If you have a down cycle and you have cash built up, you have you have [00:26:00] a cushion to be able to figure out how to make some changes, how to ramp things up.
It also means, for example, you’re not gonna feel pressured to take on work that is not a good fit for you or to take on work where. It’s not as profitable. We’ve seen this with employees where they end up taking a job at less pay than they really should be receiving because they have to.
And we, I see this with entrepreneurs all the time. They will take on clients that are difficult clients. They’re difficult to work with. They don’t pay well, they don’t pay on time. All these things that you can avoid if you feel like you have the strength and the wherewithal to negotiate more strongly.
And again, it all comes from having a cash cushion.
Porschia: Agreed. Agreed. And I. Wanna kind of piggyback on that while talking about another problem that I see and get your, feedback on it. One of my favorite [00:27:00] quotes is by Theodore Roosevelt, and it is, comparison is the thief of Joy, which I’m sure you’ve probably heard before.
And I think that’s a big problem that I see when it comes to a lot of entrepreneurs. To your point, and you mentioned this earlier, oh, I see this person doing this tactic or on this social media platform or with this business model or this service offering, this product offering. And they’re comparing themselves.
So I think I’d love to get your feedback on comparison and then I’ll give a real example, I guess first of our business. So we do competitive research and our marketing manager a few years ago, she helped with SEO and all this other stuff and she pulled together a list of competitors and we looked at, keywords and what they were doing on their websites and all of this.
And one of the main ones that I realized we were comparing ourself to, for lack of a better term, they had venture capital [00:28:00] money as part of their startup, right? And I started this business about 12 years ago, and there was no venture capital money ever within, what we do. And everything was, put initial investment by me and everything was, grew from there.
But again. We could look at that competitor and, research what they were doing. But in the comparison, is it really a real comparison to compare our business to one that even though they’re a super small business and on the surface they look like they do what we do, they have intercapal money.
That’s my example and way of positioning a problem. I see a lot to you, David. What are your thoughts on that?
David: I think comparisons are helpful and. I actually use them to see what I can model based on what I see somebody else doing in a similar kind of business model or a similar kind of marketplace.
So I look for kind of strategies or tactics that they may be [00:29:00] using or perhaps messaging that they’re using that oh. That is really smart. That could work. We could adapt this for our business. And again, it could be a similar kind of business model, but a different industry, so for example, we have a community business model.
There are a lot of communities out there. There are communities that have nothing to do with entrepreneurship. And some of them are quite successful. So I could, look at other community businesses and see, oh. These are some things they’re doing that we’re not. So I would say comparison is good for learning.
I don’t know that it is necessarily that you need to should yourself into doing something that either makes you uncomfortable or that maybe isn’t gonna work for your business. So I think you need to look at. In comparison through the right kind of lens.
Porschia: Love it. Love it. So tell us more about your business, [00:30:00] David.
David: Yeah, so we have a community business, so it’s it’s a smash in the Plateau is a platform, as you mentioned in the introduction, which includes. Our weekday newsletter and our podcast, which are free, and we have a paid membership community for entrepreneurs and honestly, some employees too.
It’s really the whole idea of the community is to connect. Like-minded people who are trying to, either they haven’t left their job yet, or they have both a job and a business simultaneously. More and more people do this, which, there are reasons to do that. Most of our members are just entrepreneurs and they’re somewhere in this trajectory of starting, running and growing their business.
Some of them are in relatively early stage, some have been in business for decades. The whole point is connecting people. Using a framework of thinking partners where you are constantly in [00:31:00] dialogue with other entrepreneurs so that you can get this impartial feedback on challenges that you face and you can offer your impartial feedback to them around challenges that they face so that.
Everybody can do better. It also offers opportunities for collaboration. It offers opportunities for introductions. ’cause relationships are really key to success in business and in life. So it ex expands everybody’s sphere of relationships and it’s really done in in a culture of caring and thoughtfulness.
Yeah, so even though we have members that are, that provide some of the same kinds of services, the whole point of being in the community is to help one another so you can be in competition with somebody else and still be supportive and helpful of them. And I’ve seen actually some great collaborations often result from people that [00:32:00] seem like they’re in competition and all of a sudden they realize, oh.
There are ways we can actually do some things together that will benefit us and our clients.
Porschia: Yeah, I completely agree. We’ll be providing a link to your website and other social channels in our show notes so people can find you online. Now, David, I wanna ask you our final question, and that is, how do you think executives or entrepreneurs can get a positive edge in their career?
David: Spend more time listening than talking.
Leave your ego at the door.
Porschia: Yes. I think that is a great advice and insight there. And especially with entrepreneurship. I think sometimes entrepreneurs have a great idea. They think they, know everything about that idea, to your point about ego and to be successful, especially nowadays with technology and [00:33:00] everything changing so fast, like you were mentioning earlier, I.
You’ve really gotta learn, you’ve gotta grow, you’ve gotta develop and leave that ego at the door. So thank you. David. You have shared, good question. Yeah. Yeah. I think you’ve shared a lot of wisdom with us today, and I’m sure that our listeners can use it to be more confident in their businesses.
We appreciate you being with us.
David: Thank you so much, Portia.
Porschia: This episode was brought to you by the Brave Bird Career Alliance, the go-to membership designed for seasoned executives and ambitious professionals with everything you need for career planning, strategy, training, and support. Thank you again for listening to the Career 1 0 1 podcast. I hope you have at least one key takeaway that you.
Can use in your own career. If you [00:34:00] enjoyed hanging out with us, please rate, subscribe, and share this podcast. Until next time, here’s to your success.
