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Software Development Career Coaching
Feeling stuck in your software development career?
It’s all fun and games when you’re a noob at working on software teams.
But if you’ve been in this field for a bit, you’ll suddenly be faced obstacles that decide whether you give up – or become a true professional. Maybe you’re having trouble meeting deadlines or people’s expectations. The relentless advances in AI and never-ending explosion of new frameworks and programming languages could have you concerned about staying relevant. Or maybe you’re struggling to keep a healthy work/life balance.
It can feel really overwhelming to deliver software, learn on the job, keep increasing your value in the market – and then conjure up the energy for a meaningful life OUTSIDE of work!
You’re not alone.
If you’re getting frustrated (or maybe even bored), you probably just need a little encouragement – and some perspective.
Whether you’re a developer, product manager, or any other role that works on a team to deliver software – many of our challenges are the same. Other people at your job may not admit it publicly, but you’re definitely not alone in how you feel. This industry can chew people up and spit them out without a care in the world about how it impacts their life. Without a plan, everyone in the industry is equally in danger. They just may not know it yet.
decisions a confusing road to navigate.
One of the things that’s unique about software development is that you’re using emerging technology (and often combining tools and APIs in ways that have never been done before), so predictability isn’t a luxury you have. We have all these processes like agile, devops, and system design to try and cope with this. But many managers and executives fear change. So you need to be careful about how you proceed with your career in software development.
While most employers will say they care about your career, don’t put your future in their hands. Your job is mostly about getting them results, so that’s what you should focus on when you’re at work. But the second what you need to do to keep growing doesn’t benefit them, they’ll try to convince you it’s not important. So keeping your career in IT growing is really up to you.
Your fortunes have just changed by stumbling on this page!
Well, fear not! That’s where my coaching comes in.
Many people are confused about what career coaching really is. Coding bootcamps often offer entry level developers a “career coach” to help them pass interviews and get a job. But that is coaching you on interviewing and hiring – not your actual career.
The truth is, getting a job is the easy part of a software development career – being successful once you’re working is the hard part!
A professional career coach is a mentor with deep experience in your industry. They can guide you through the treacherous waters of day-to-day challenges on the job. They can help you discover your best path to success over multiple jobs. They can help you look over the history of your career and identify patterns in where you may be stumbling. And they should be capable of helping you figure out if what you’ve been doing is really working – or if it’s time for a shift in your career focus.
Maybe you need to be more diligent about breaking work down before committing to estimates or designs. Sometimes what’s missing is communication, leadership, or persuasion skills. Maybe you’re not delegating enough work to other people so you can reduce your stress. Sometimes you need a change in your habits to keep your mind sharp and your body healthy. Other times a change in your mindset or attitude would do wonders.
If you’re trying to figure this out all on your own, I know how hard that can be!
I have big blind spots in my own life and career, and that’s why I’ve found trusted advisors over my life to guide me too.
Hi, I’m Jayme
As a software architect and consultant with 25 years of experience, and having worked on nearly 40 software projects to date – I’ve battled with the same challenges you have that come with working in this field. I didn’t plan to be career coach, but as I got older I started seeing a BIG problem.
Over the last 15 years of my career I’d been mostly working as a technology consultant to help people work together better to deliver software. And whenever I would meet people at a new company I was hired to help, I’d see the same depressing thing. Smart and motivated people, who found themselves burned out and frustrated – with nobody to help them get unstuck.
Your coach at a glance
How I became a coach
If you’re considering help from another person with something as precious as your career, it’s important to know what motivates them!
So let me share a quick story about how I got here…
Around the time I turned 41, several problems in my personal and professional life suddenly collided. My marriage was falling apart, my oldest son was in danger, and my job had become a non-stop series of fighting fires on projects that were mis-managed. I was struck with chronic insomnia and had to quit my job because I was only sleeping 3 hours a night. I couldn’t think. Over the next couple of years, I spent all the money I’d saved over my career to try and recover from serious burnout. With my life turned upside down, I struggled with figuring out what went wrong – and where to go next.
It was in the midst of that confusion when it finally struck me. I needed to stop helping companies get rich off their customers, and start giving back to the people who work so hard to put food on the table for themselves and their families – the employees. Thankfully my wife and I worked things out, my son got back on track, and I found myself self-employed with a hopeful, but uncertain future.
I continued doing software development related work as a consultant, but part-time. And I started a YouTube channel to share the experiences I’d had in the industry, hoping to help the next generation not fall into some of the same traps I did. Nobody seemed to warn me about these or talk truly honestly about what I was up against on the job. Soon afterwards I began my coaching journey.
How I can help you
The ironic thing about a career in software development, is that the media and most “thought leaders” focus mostly on being skilled with technology. But anyone who’s been in the industry for a while will tell you that’s not the biggest challenge of working in this field. It’s what it requires of us as people. If you can’t communicate well, respect differences of opinion, and rally support for your cause – your technical skills are worthless.
Improve your relationships
I’ve been a husband and father for 25 years, and in that time learned a lot about how to have healthy relationships – mostly by doing it the wrong way at first. I learned the hard way that trite sayings like “happy wife, happy life” were bullshit. We needed to be honest, and wrestle through some messy stuff to stay together.
My wife and I changed over the many years we’ve been together. But not because we forced each other to. We realized we cared more about each other than being right. And we learned to stop talking past each other – and to listen better. That experience naturally translated into me communicating way better with my employers and consulting clients, and now I’m bringing this and other things I’ve learned along the way into the careers and lives of people just like you.
Reinvent your developer value proposition
Over the many years I’ve been in this industry, I’ve had to change drastically to stay growing.
I started out as a QA tester. Then I helped customers write their own code to integrate with our software. Then I wrote web applications. Next I was creating frameworks and architecture. A little later I got into consulting. I had to learn more advanced data analytics and business intelligence. Then it was expanding those skills into the cloud. Soon I was sitting in meetings alongside sales people, convincing clients that were skeptical why working with our consulting agency would help them be successful. And then I began offering process coaching for devops, agile, lean product management, and a host of other ways of working together better.
If you’re under the impression that the knowledge you have today will keep you going for very long, you’re in the wrong industry. The good news though, is that it’s getting easier than ever to learn. With Github copilot, Chat GPT, StackOverflow, and YouTube – we have access to resources I never could have dreamed of when I started out to help cope with learning. But even then, you need to be strategic about how you proceed. Some of my clients come to me overwhelmed because they’re trying to be experts at everything. Keeping growing is important, but it has to be done sustainably!
A customized coaching experience
Despite my experience, I have the humility to realize I sure as hell don’t know everything. This field has a bottomless pit of knowledge and niches. But there are some universal truths. That’s why, as a coach, I work with each client differently. People who work in the software industry have such a wide variety of unique experiences that they require a customized approach. There’s no one-size-fits-all solution to the challenges we face in our software development careers!
With that being said, we do face many of the same problems. That’s why I offer 6 outcome-based coaching packages that are designed to help you overcome the same trials we encounter again and again in the IT industry. From imposter syndrome to poor communication skills, from selling your value to employers to time management struggles, and even recovering from workplace burnout – my packages have got you covered.
If you’re skeptical – I get it. Yes – there ARE countless people online claiming to help you “level up” with your career in software. And though they may mean well, most people do not have nearly enough experience in this industry to produce changes in a person’s career that have a lasting effect. To be effective with such a daunting task, a coach needs to have seen the good, bad, and downright ugly in the software industry – and found a way through it without becoming jaded and bitter. Instead you typically have either the person who became a coach soon after finding the job too hard, or the person who worked at one or two high profile companies and now think that they’re God’s gift to programmers.
I’ve made many mistakes, and I’m far from perfect. I’ll probably make more. But I’ve been surprised to learn something after all I’ve been through.
I really love coaching – and my clients seem to love it too.
What’s it Like to Have a Software Development Career Coach?
Ever tried to learn a sport or a musical instrument?
You probably know working with a teacher can be way faster than trying to learn it on your own.
But a coach doesn’t actually kick the ball or play your instrument for you.
This is the same relationship I provide as your coach.
The benefits of confidential advocacy
The politics at software companies can make it hard to be honest.
A big advantage to coaching with me is having a confidential advocate for your success.
Being able to speak frankly with me lets you work through situations with coworkers without the fear of politics.
It also lets you share struggles with yourself that are too sensitive to discuss at work.
I don’t do the work for you – I help you do the right work.
It’s taken me 25 years to learn the software development techniques I use.
And I know many of them can help, but you still know your unique situation the best.
So I use the co-active coaching method.
The industry generally agrees this is the best method for coaching people.
My goal is to help you be transformed into the best possible version of yourself.
Depending on what you need, I may:
- Help you create structures to hold you accountable
- Teach you methods for practicing new skills
- Ask you to practice awareness exercises to get rid of bad habits
- Suggest ways to protect yourself from people who can damage your reputation
- Offer strategies for your online presence and networking to get better opportunities
- Roleplay to prepare you for interactions with coworkers
…and more.
But I believe the answers to many of your questions are within yourself.
You should be improving your own intuition and abilities by working with me.
If a coach makes you dependent on them, they aren’t a coach – just an expensive “guru”!!
What Clients are Saying
“Working with Jayme has been a wonderful experience that boosted my confidence tremendously. The nature of the tech hiring process, and dev culture in general, too often led me to question my abilities and self worth.
Minutes into our first session, I realized I wasn’t alone! Before working with Jayme, I was miserable at a dead end job – desperately sending my resume to any job posting I could find. Since then I’ve recalibrated my goals to be in line with who I truly am as a human being. I’m working with great people and enjoying what I do.
Jayme’s positivity and experience in the industry could be helpful for just about anyone. He’s truly honest and will happily tell you what he can and can’t do without any façade. His developer coaching truly changed my life for the better, and I highly recommend it.“
Dan Kurfirst
Frontend Developer
Joe Sak
Senior Developer
“I hired Jayme last year to help me improve as a leading member of my team, and I have to say the results have been phenomenal! Since working with him as my career coach, I’ve demonstrated higher level skills, and became a role model for my team – even my CTO!
I’ve also gotten better at conflict resolution and persuasion, learning how to choose my battles and show up better prepared for high stakes conversations. I’ve learned more about how to advocate for myself with management, and to push my team in a healthy way for higher standards. At every performance review, management considers my contributions to be invaluable.
I’ve also improved my work-life balance. I used to throw myself into the work more than my employer even required of me. But this led to burnout and resentment. Jayme pushed me to put my creative energy into my free time more, and to take regular personal time off. I’ve seen growth in my personal pursuits, such as learning to play guitar.
If you’re on the fence, jump over and hire Jayme today, you will not regret it!”
“My first job out of college was working for a small company. As a result, I didn’t receive much mentorship and was basically trying to find my own path and figure out how to grow as a developer and keep up with industry standards.
When I decided I needed to move forward elsewhere, I was new to the software engineering interview process and wasn’t sure how to properly prepare for it. Jayme reassured me that I wasn’t alone and helped me immensely in these areas.
The process can be grueling, but Jayme helped me develop a better mindset and get to a better work/life balance. I’m looking forward to continuing to work with Jayme again in the future, and would definitely recommend him to anyone else.“
Brendan Williams
Software Engineer
Brian Fitzgerald
Associate VP of Technology
“Let me put it simply: Jayme is the man. The information and guidance he shares, based on his extensive and diversified experience in the world of software, is TRULY NEEDED, and yet very rarely discussed.
Through his work, both in the form of recorded content and custom sessions, he shines a very important light on how to have a healthy career, healthy work life balance, healthy mindset, and how to be a true professional in the world of software development.
In our one-on-one coaching sessions, Jayme shared a lot of value in helping me find my personal areas of strength and encouraging me to lean into them, letting those strengths be a distinguishing factor in my craft as a software professional. That’s been a huge help
I’m so glad I stumbled upon Jayme’s content when searching “programmer burnout” one day on YouTube, because I’ve been appreciating Jayme as a trusted resource and mentor ever since!“
“If you’re feeling stuck in your career, you’ll need to hire a coach sooner or later. Anyone doing development needs to break his elitist mental barriers.
Recharging & accumulating perspective takes a lot of time. No matter what level you’re at in your career, eventually you reach a plateau from which you’ll either go up – or down.
Hiring Jayme as my coach has helped me cut that plateau / recharge period in half & go upwards – call it a career-hack if you will.“
Robert Rusu
CTO / Lead Developer
J. Max Shaer
Technical Project Manager
“Prior to meeting with Jayme, I was trying to decide whether to go back to school or find a new job. I was split on what made the most sense for my career, and he helped me make that decision. Rather than sticking to prefixed agendas, Jayme actively listens and asks challenging questions to help guide you through the process of making key career decisions on your own. Jayme has helped me restore confidence in myself and my career path.
Additionally, Jayme’s plethora of industry experience makes him a very reliable resource to help you find a new job opportunity. From preparing your resume to nailing your interview, he will give you all the tools you need to successfully lock down your next position in the technology industry.”
“I was fortunate enough to work with Jayme during my recent client project, fulfilling a new role as automated QA.
Jayme guided me through preparation for testing in cloud environments, and slowly and patiently taught me everything he could about DevOps with which I’d never worked before.
Without Jayme’s help, I don’t believe I could have fulfilled my responsibilities in time for the client. I highly recommend him for mentoring others.“
Timothy Hall
Senior Consultant
Curtis Randolph
Animator & Digital Asset Manager
“Working with Jayme was great. I was in the position of having only worked for one company, and having no idea how valuable I was to the industry at large. We worked together to create a negotiation plan for a promotion, and Jayme was able to help me write it using language that management could hear and be interested in.
While that negotiation did not ultimately work for me, my talks with Jayme gave me the confidence to walk away from the 6-figure salary they were offering. I’m now working on starting my own business, and pursuing that vision with a confidence I didn’t think I’d have.”
How To Get Started with Software Development Career Coaching
To find out if you’re a good fit to participate in this software development career coaching program:
Schedule a free 45 minute initial consultation with me over Zoom* videoconferencing.
Your free consultation helps you get to know me and explore your situation before investing in services.
At your consultation we’ll talk about:
- How you got here and where you’re going
- Your most urgent desired goals and strategies for impacting them
- Whether you have the mindset to get everything you can from coaching
If I agree to take you on as a client, you can pick the software development career coaching program that fits your needs.
You can enroll in a monthly subscription, or purchase a pre-paid bundle of sessions.
* Zoom is a trademark of Zoom Video Communications, Inc.
Schedule a Free Career Consultation
Don’t worry, this consultation isn’t a sales meeting in disguise. You won’t be pressured to work with me or make a decision on the spot. It’s a chance to share your situation and get some feedback from me on whether I may be able to help you. I’ll send you links afterwards to read more about whatever coaching package I recommend for you.
But please… don’t bother booking a consultation if you’re “just curious”. I have limited time to meet with potential clients.
I only work with clients who are willing to be open, try new things, and do whatever it takes to reach their goals. So If you want to get back to loving your career again, it’s going to take an investment in your time and money, and keeping an open mind. Anyone who tells you improving your career won’t require anything from you, is selling you false promises.
But if you really want to get unstuck, you don’t have to struggle through it alone! I’d love to get to know you a little – and help you figure it out!!
Schedule a free 45-minute career consultation to discuss your situation with Jayme below:
As of 5/15/2023, I have 4 openings for new clients.
Already had a consultation? Choose the software development coaching program that’s best for you:
Career Coaching Packages
Achieve common outcomes many professionals want from their software development career.
Career Coaching Bundles
Get help with outcomes not covered by the coaching packages above.
Sessions may also be booked individually for $300.
What happens when I enroll?
Upon purchase of any coaching, you’ll immediately receive an email with a unique link you can click to easily book your session(s) online.
The online booking system allows you to see what time slots Jayme has available so you can book single, or recurring sessions.
Jayme is available for sessions from 1:00pm – 5:00pm Central Standard Time (CST), Tuesday through Thursday.
How coaching packages and bundles work
Coaching packages and bundles are designed to let you meet with Jayme every other week.
However you can schedule your sessions any time Jayme has availability over the term.
Each session you attend will reduce those remaining in your coaching product or bundle by one until they’re all used up.
Learn more about coaching packages and bundles in the terms & conditions of coaching, or contact Jayme for any questions you have.
Ready for experienced, confidential guidance to accelerate your career?
Schedule your free consultation today:
Frequently Asked Questions
It’s hard to be completely honest with people employed by the same company as you. There’s competition for pay and promotions, and egos get in the way. I provide confidentiality, and I’m an advocate for you with no conflict of interests.
I can provide you with the opportunity to be honest and vulnerable, and share challenges you’re having with specific people so you can do something about it. I would often vent to my wife about struggles at work. And while she’d listen to my problems – I couldn’t really expect her to help me through them.
One of the biggest challenges in software development is having a healthy work/life balance. Depending on your situation, I may recommend books, products, or activities to do to balance out your life with working in this industry. There’s no “silver bullet” solution to stress and anxiety on software projects – each person is different.
With that being said, I’ve found some things that work very well for me and learned a lot through trial and error. I believe the unique experience I have with trying to raise a family while working in software development can offer you solutions a regular life coach can’t.
From a technology standpoint – I can advise you on your product’s design, architecture, release strategy, and how you and your team work together as examples. I’m paid highly as a consultant because of the wide variety of problems I’ve solved in different industries. But this service is not for debugging and working through specific programming algorithms. It would be too expensive for you due to the time needed.
Software development projects and the nature of our work can be incredibly contextual. So it’s likely that what we do together will be specific to a combination of variables that make your situation special. Depending on what you’re trying to achieve, I may offer coaching activities you can do outside of your session (provided as PDF files you’ll print out and complete usually). I may also suggest both physical and online learning resources as necessary.
We’ll be sure to discuss together how realistic it is that you can actually do the activities, or learn from the resources, before you commit to anything. Having been in this industry a long time, I know time is one of the hardest things to find in our career. I want to help you get slack back into your life again, and I wouldn’t be doing a very good job if I overwhelmed you with too much homework!
I’m happy to provide guidance on what you need to do to win in your pursuit of new positions! However I will not provide a reference unless we’ve worked together on a project. It’s important that your reputation is kept ethical and honest as you grow.
Getting promoted can be a complicated process, but there are several strategies I’ve used that have worked well for me. How we approach this will depend a lot on how measurable we can make the goals you feel will put you in the best position for promotion, as well as the personalities of the people you work with. I cannot guarantee that you’ll get promoted if you apply my guidance, but I’m confident we can put you in the best position possible to be considered if you’re willing to put the work in.
I’m all too familiar with confronting high pressure leaders. As a neutral advocate for you, I cannot directly get involved in the politics at your company by communicating with others on your project(s). This is why I’ll help you learn consulting strategies as needed to earn respect for your ideas and convince people yourself!.
You can cancel your session up to 24 hours in advance. If you cancel by then, you’ll be refunded in full.
You may email me about scheduling questions, or to respond to materials I send you. And feel free to discuss any of the content on my blog, YouTube channel, or podcast with me there. I personally invite you be part of our growing community of healthy software developers! You can also find links to all my social media accounts at the bottom of this web page. But please don’t abuse these channels to discuss your case – you should book a session for that. 😊
Some people prefer sharing high level ideas to a big audience. And while it’s fun to get up on stage, make people laugh, and throw ideas around – it takes getting your hands dirty to actually put them into practice. I’ve spent my career doing the hard work needed to implement these ideas one on one with people on real teams.
I’ve given many presentations over my career and they are great tools for making decisions, or raising awareness. But achieving goals and overcoming challenges is done by people working closely together. This is why I offer one-on-one coaching.