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Make Goals Inevitable with ADHD: Stressors and Entrepreneurship with Skye Waterson (2/2)

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Does the ADHD brain experience stress differently in situations like being laid off, for example? According to Skye Waterson, ADHD coach and our guest in episode 314, stress actually has the potential to hit you harder after a crisis.

In this discussion, Skye shares practical tips for setting achievable goals as a job seeker or an entrepreneur and the importance of taking a long-term view throughout the process. We talk about the strengths of the ADHD brain in the tech field and how to determine if a work environment is the right fit when you’re interviewing. Skye also shares the reasons she decided to walk away from academia to start a business and some of the lessons learned along the way.

Original Recording Date: 12-29-2024

Skye Waterson a former academic turned entrepreneur and ADHD coach. If you missed the first part of our discussion with Skye for a slightly different perspective on the ADHD brain, check out Episode 313.

Topics – Stress and the ADHD Brain, ADHD Strengths in Tech, Setting Goals and Maintaining Accountability, Walking away from Academia, Reflecting on Entrepreneurship, Job Interviews and Finding an Environmental Fit

2:34 – Stress and the ADHD Brain

  • Nick suggests we talk about stress in the context of the current job market. We’re seeing layoffs across tech and other industries continue. How do these stressful and traumatic situations affect the ADHD brain differently than perhaps those who do not have ADHD?
    • “There’s no conclusive thing that I can think of in the research that I’ve done that we experience stress in a different way…. What I would come back to with ADHD is that we have impulsivity struggles and we have executive functioning struggles. And so, it comes back to this idea that you’re ADHD all the time. When something stressful happens to you when you have ADHD…you have to deal with all of the emotional regulation, all of the thinking…all those things can mean it hits harder.” – Skye Waterson
      • People with ADHD can struggle with rejection sensitivity and self-criticism. Self-criticism could be partially due to receiving a lot of criticism when younger (positive or negative).
      • Stressful events can hit harder as well if you have PTSD or other mental health struggles.
    • Skye gives the example of getting into a car wreck. After it happens, you have to call the insurance company, figure out what to do with your car, and do many other things.
      • “And especially once the dopamine is gone…you might be good in the crisis, but post-crisis, you now have to pick up all of this executive functioning task work and do emotions. So, you might be struggling way longer than somebody else might be struggling…because now you have to deal with all this actual admin work as well.” – Skye Waterson, on experiencing stressful situations with ADHD
  • If we put that same set of challenges in the context of someone losing a job, someone would need to figure out how to spend the time they have left at a company (could be some or none), update their resume, update LinkedIn, and decide what to do next.
    • “I’ve worked with a lot of people in that job space…. Essentially what you’re doing is you’re starting a small business called finding another job. It’s really complicated…. Really it does have to be a system that you break down…. What is my goal? My goal is to get this job. What are the steps that make this goal inevitable in a day? …Make it an achievable goal for you to hit those things and focus on that and give yourself dopamine for that rather than…my goal is to wake up every morning and try and get a job. That’s very, very difficult and not very fun from an emotional point of view.” – Skye Waterson
      • Some of the people Skye has worked with chose to begin a small business on the side after being impacted by a layoff. It’s certainly one option for people but not the only one.
      • Part of the system might include a specific number of people to message per day, a specific number of resumes to send per day, and a specific number of jobs to check in on. These goals should be achievable for you.
    • Would the amount of dopamine required to work toward getting another job each day be even higher because of the compelling event that put you into a stressed state?
      • Skye says yes but you also do not have to start immediately. We can sometimes go into crisis mode and use the dopamine of stressful events to push us forward. It can seem like a crazy burst of energy that propels you until you crash.
      • “In the moment when it happens…and if you knew that this might happen it can be good to prepare this in advance…you want to go ahead and do something grounding. Things you liked as a kid are very helpful. Give yourself Chinese food, watch a movie with a friend…things like that could be really good. But have a time in your calendar that you’ve blocked out that is ‘plan to find another job.’ Give yourself a 2-hour window. Put it in your calendar like you’d put a doctor’s appointment. Take yourself to a coffee shop if that’s going to help you stay motivated to do it, especially if you’ve been used to a working environment, and once you’re there, give yourself a really nice cup of coffee (maybe a chocolate biscuit with this one) and then go ahead and plan it out.” – Skye Waterson
      • Skye recommends an AI-powered app called Goblin Tools to help with planning / breaking down things into steps. This app is free and is designed to help people with ADHD. You could search for “find a job in X industry in X country” for example, and the tool will break it down into steps that you can convert into a daily rhythm (focusing on the input and not the output) and overall system for finding another job.
      • With ADHD one of the struggles with executive function is working memory. It can be hard to break things down into subtasks once you have a high-level task or goal. Skye likes to use the example of buying a new rug to show all the subtasks required (measuring, finding a new one, going to get it, deciding what to do with the old one, carrying it upstairs, etc.).
      • Nick has seen the challenge of breaking things down into steps firsthand through working with his daughter. It’s like there are dependencies that are missed. But once Nick’s daughter has the list, it’s easy to move forward and make progress.
      • “A list, a daily routine, a reward,…making it a realistic thing….” – Skye Waterson, on the elements of a good system for a job search
      • Goblin Tools can also provide a rough time estimate for tasks. They probably are not really accurate, but it can help you understand everything will not happen tomorrow and that it will take time.
  • Is it easier for the ADHD brain to find closure after a stressful event (loss of a job, death in the family, etc.)?
    • Skye has not seen any evidence to suggest this is the case.
    • “It’s more the case that the admin of all of these things can tend to linger for a lot longer for people who are neurodiverse. So, they might still have boxes of things that they haven’t organized, for example, for years after other people would have organized them.” – Skye Waterson
    • Part of the reason Skye recommends using the prioritization filer we discussed last week was to account for things which might be lingering in someone’s mind for a long time (like things that have gone unorganized).
    • Some of the strengths of ADHD are creative problem solving, original thinking, etc.

11:53 – ADHD Strengths in Tech

  • How might the strengths of the ADHD brain play out in the world of technology?
    • Nick mentions a great discussion from the ADHD Skills Lab podcast with guest Lisa Ballard about working in technology sales with ADHD.
    • “There are a ton of strengths. When I work with people who have ADHD it’s really about how do we mitigate the struggles so we can focus on the strengths. We’re not living a life of just mitigating the struggles, and sometimes people think that…. We know from the research that we’re original thinkers. If you give a person with ADHD a task and an example of the task, people who are neurotypical will tend to iterate around that example. People who are ADHD be fully left field…and completely originally redesign this thing…. You can sort of see how that would work well if you were in a workplace and you were solving a problem. One of the best things about ADHD in the technology space is that we are out of the box thinkers. We love pulling a solution to a complex problem out that no one else has seen before. And we’ll usually have an original perspective on why it exists, what we should do about it…. They’re great people to have in the room when you are ideating, when you are problem solving, when you are bug fixing even…all of those spaces.” – Skye Waterson, on ADHD strengths and how they play out in tech
  • Would this support the theory that many entrepreneurs have ADHD?
    • Skye says ADHD is so common in entrepreneurs that people just assume entrepreneurs have it instead of the other way around.
    • Skye mentions two types of entrepreneurs:
      • The first type would be someone who has ADHD, never really worked on it, managed to focus without burning out completely, and became a very successful business owner with multiple employees. This person has not sorted out their own ADHD.
      • The second type is the entrepreneur with ADHD who is struggling (and maybe burning out) who seeks out strategies and support.
    • “Sometimes people will say ‘I have ADHD, but it doesn’t affect me….’ You should talk to the people in your office. It might.” – Skye Waterson

14:43 – Setting Goals and Maintaining Accountability

  • How can the entrepreneur stick to the business they have chosen and focus on it without getting distracted or losing interest in it completely? One of the ADHD traits is losing interest in things after a time and abandoning them.
    • Skye says it’s very hard, and she’s spoken to other entrepreneurs with ADHD about this.
    • One way to combat this is to only do things that add to what you’re already doing. If you only help people in the technology space, you should only decide to do things that help people in the technology space.
    • Another way is to set a very long-term goal for your business (possibly a 25-year goal) and then smaller, shorter term goals or targets you’re working toward along the way (i.e. where you might want to be in 5 years or even 1 year, etc.). Ng
    • Having an EA or executive assistant can also be very helpful to hold you accountable and to be honest when you have added too much to your plate. External accountability can be very helpful.
  • Can we have people hold us accountable in a way that we don’t feel the shame of not accomplishing a goal or abandoning a goal? With the challenges in emotional regulation that come with ADHD, does the sense of shame become greater?
    • Skye says yes it can be greater. But the problem may lie with the goal you have set.
    • In business, we often talk about the idea of a BHAG or big, hairy, audacious goal. It can be easier to not feel shame if the goal doesn’t have a strict timeline.
    • When working with an executive assistant, ask them about their goals to ensure their goal fits within yours.
    • Skye gives the example of having a goal to create a business that eventually becomes a media empire but at the same time is sustainable and will support balance with family life.
    • “If you said to somebody, ‘that’s my goal,’ and maybe part of that, because we do want some kind of measure, is ‘I want my business to hit 6 figures by the end of the year. That’s my goal.’ If you don’t hit 6 figures by the end of the year because something happened, it doesn’t super matter because you’re working toward a 25-year goal…a media empire 25-year goal. This was just a bit of a valley year. And so, you’re still going toward the goal but you’re just adjusting the goal posts when you get there. Don’t adjust them prematurely….” – Skye Waterson
    • Skye is advising us to take a longer-term view of our goals and to remind ourselves of the progress we have made, even if the progress was not as much as we wanted.
    • Don’t think about missing pre-defined targets as failures but rather as puzzles to solve while you make progress.
    • “This is a lot easier to do when you get out of the ‘I need to make enough money to survive’ part of business. But usually, when you’re in the ‘I need to make enough money to survive’ part of business, you have enough dopamine. It’s that middle piece that can sometimes be the problem when you’re scaling, you don’t yet have the finances to bring other people on to support yourself…to be able to get out of the things that you don’t love. You’re starting to do that, but you’re in that…complicated middle space.” – Skye Waterson, speaking to the dilemma of the solo entrepreneur
    • Nick says at this point effort has to go up because you are not quite big enough as a business.
    • “There’s that bit where…there’s no one, there’s no money, and it doesn’t super matter what the goals are because you’re just starting. No one will really notice. You can sort of play around in that space and figure it out. And I did this for years…. The middle piece is often where people find themselves stuck. They’ve got something. It’s making money, but they don’t know how to hand off those tasks and in what order and how to focus to do the thing.” – Skye Waterson
    • When you reach the point of being able to hire someone to help you, that can come with its own set of unique challenges according to Skye.
    • Before starting Unconventional Organisation, Skye helped her husband run a frozen foods business during which she learned a lot.

21:43 – Walking away from Academia

  • Why did Skye become an entrepreneur, and how has she seen the challenges and strengths of ADHD play out during that experience?
    • Skye originally wanted to be an academic. Being part of that world involved a lot of short-term contracts and grant writing. It did not seem as stable or as free as she would have liked.
    • “I didn’t really know what to do about that, but I did start looking at entrepreneurship at that time.” – Skye Waterson
    • Skye loved art and tried to sell a few paintings, but that didn’t really work well. She continued experimenting.
    • Skye’s then boyfriend (and now husband) who also has ADHD was starting a business selling frozen food in New Zealand. Skye helped him with the business and gained some experience, but the business fell victim to COVID shutdowns.
    • “It taught me a lot…. The thing I love about business is no one tells you no…and this kind of goes back to the idea of getting let go…. When you’re in a workplace, you can do your absolute…best, and you can still get fired, or you can still not get the promotion. There can be politics. There can be other things. When you are running your own business it’s sort of like a big giant puzzle. Yes, someone can say no to this thing, but maybe you just need to rethink what you’re doing, or maybe you need to talk to a different audience…. There’s often a solution. There’s something to do. And that for me was very good.” – Skye Waterson
    • When Skye started as an ADHD coach, she did not anticipate it becoming a large business, but she did hire a business coach. Skye knew from her previous experience how important this would be, and she also hired an executive assistant for a few hours per week. Skye highlights these two decisions as helping her grow and develop tremendously.
    • Skye would eventually decide to leave her PhD program and tells us it was one of the most difficult decisions she’s ever had to make after spending so much time pursuing that path. Skye found that her PhD supervisors / advisors were supportive of her decision to start a business and leave the program.
    • Skye is still involved in research and has a researcher on staff. Skye’s podcast, The ADHD Skills Lab, is a platform to discuss the current research which she can then turn into helpful teaching tools.
    • “In that way, it’s been great because businesses are like this little interesting engine that you can craft to however you want to work…. I still do the things I want to do. I just do them in a slightly different way.” – Skye Waterson
    • Nick thinks Skye has taken the things she enjoyed from academia and put them into a slightly different context.
    • Skye was at the dissertation stage when she left her PhD program, having already done the research that just needed to be written up. She also had a small baby at the time.
    • Skye said she was going to pursue a PhD and then didn’t finish it, but it’s ok that she didn’t finish. There is no shame in it because that was a small step in a much longer-term journey or goal. Skye is modeling for us that her own focus is on longer-term goals.

26:56 – Reflecting on Entrepreneurship

  • What are some of the things Skye wishes she had asked about being an entrepreneur that she had to learn only after becoming one?
    • Skye wishes she had asked how to make money. That was definitely harder than it looked.
    • It wasn’t until after building a 6-figure business that someone told Skye how to do sales properly. She mentions she had been order taking rather than making sales.
    • “At the end of the day the number 1 thing you want to do is sell. Sales is super important, and I’ve had amazing business mentors throughout my career. That’s been the thing that has been most helpful. Do you know how to sell something to someone? …I knew how to do academia. I could talk for ages, but I didn’t know to sell something. That was big.” – Skye Waterson, on learning how to sell
    • Skye would highly recommend the book Spin Selling.
    • Skye has also found putting on her psychologist hat really helpful within the context of selling. People have a problem, and you may have the solution to that problem. But you need to understand the problem before proposing a solution.
    • “So, if somebody has this problem and you have the solution to this problem, then it’s…your job to make sure you understand all the objections to the problem…. I did clinical psychology in my undergrad, so if you think about it from that perspective, I find that much better than sales.” – Skye Waterson
  • When selling a product or service, in many ways it’s like a bi-directional job interview. The entrepreneur can say no to the wrong kind of client / customer.
    • Skye tells us she has said no to potential clients before and that there is a qualification process one has to go through before working with her.
      • Often times saying no to someone is because the person may need more intensive mental health support.
      • Skye only supports clients (business owners) who do high ticket, high value products.
    • Skye mentions most of her work being centered on helpful content creation and development. Some people who have found the content helpful are potential customers and can then be taken through the qualification process to determine if they are a good fit for the product or service.
      • Skye says in this way, it feels less like what we expect traditional sales to be, but in reality, this process is what high-level salespeople are actually doing.
    • One of the patterns we’ve seen in the careers of previous guests is using content creation / public proof of work to stand out in the job market. Just as it helps entrepreneurs like Skye sell a product or service, it can help individuals land a new job opportunity (even if it’s unexpected).

31:41 – Job Interviews and Finding an Environmental Fit

  • Within the context of a job interview situation, what are some of the things the neurodiverse individual can ask to pinpoint any red flags in a potential work environment?
    • The number one thing for Skye is to understand the options for flexibility in the workplace. When you are given the chance to ask questions, consider asking:
      • What are your different workplace options?
      • What are the different ways that people in your office work?
    • “Often times with ADHD the thing we’re looking for is an environmental fit…. What we want to know is are you going to get dirty looks every time you put your headphones on? …If you just said, ‘I’m really curious about the different ways people in your office work. Is everybody at their desk? Do people have their own offices? Do people work from home? What are the different options?” – Skye Waterson, on environmental fit in interviews
      • Some environments may have flexible working hours as well.
      • If the options for working sound like a fit, Skye would also recommend (if you can) speaking to someone else who works for the company (in the office or remotely) to get the inside scoop on what it’s really like.
    • Ask about whether the work is project based or repetitive. Will there be clear deadlines, or will new tasks come from multiple different departments every day? Either can be fine, but it depends on what you as the job seeker with ADHD want.
  • Should someone share their neurodiversity openly during the interview process?
    • Skye says this is a very personal decision and that many people choose not to share it in an interview scenario unless it will have a big impact on the workplace.
    • It is more likely for people to share their neurodiversity once others get to know them as a person. This helps avoid stereotyping from others.
    • “Instead of saying, ‘I have ADHD,’ you might say, ‘by the way, I work best in these environments.’ So, you’re giving them the context, the information about what ADHD is without saying, ‘I have ADHD….’ You might say, ‘I have these characteristics,’ whatever it is that is important to you about expressing from the ADHD.” – Skye Waterson
      • You could say that you like strict deadlines, for example.
      • Nick suggests expressing what you want to express to multiple people throughout the interview process (recruiter, hiring manager, others on the team, etc.) to gauge responses.
      • Even though a company may not advertise the flexibilities an individual with ADHD might be looking for, the right manager and the right team could be the fit needed.
      • Skye says one challenge of the workplace is that it is team based, and different department managers may have different rules.
  • To reach out to Skye or learn more about her work…

Mentioned in the Outro

  • Nick loves the idea of making your goal inevitable within a day or setting yourself up so it is a given that you will hit your goal. It does involve breaking things down into smaller steps and chunks that are parts of systems and processes, but it sounds a lot like we need to develop a routine we can use to work toward our goals (like finding a new job) during the time slot we have!
    • Have you tried Goblin Tools yet? If so we would love to hear how you use it! Send us an e-mail.
    • This development of a routine can translate to preparing for the interview process. For example, we can develop the go-to questions about the type of work environment that best suits our brain or working style.
  • We’ve had a number of discussions with guests about deciding to stop doing something that once took a great deal of time and effort. Skye decided to walk away from her PhD, but taking the longer-term view helped her gain perspective on that single step in the journey toward something else.
    • Nick feels like he heard an episode of the Truth, Lies, and Workplace Culture Podcast that discussed the idea of no experience ever being a waste. That experience in academia wasn’t wasted for Skye. She uses many of those same skills and more as an entrepreneur and business owner.
    • Seth Godin as said deciding to stop doing something is a gift from our past self to our future self.

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